HRP20010866A2 - 13-methyl-erythromycin derivatives - Google Patents

Info

Publication number

HRP20010866A2

HRP20010866A2 HR20010866A HRP20010866A HRP20010866A2 HR P20010866 A2 HRP20010866 A2 HR P20010866A2 HR 20010866 A HR20010866 A HR 20010866A HR P20010866 A HRP20010866 A HR P20010866A HR P20010866 A2 HRP20010866 A2 HR P20010866A2

Authority

HR

Croatia

Prior art keywords

crarb

alkyl

nar

substituents

compounds

Prior art date

1999-05-24

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 claims description 420
• -1 4-phenyl-imidazol-1-yl Chemical group 0.000 claims description 117
• 125000001424 substituent group Chemical group 0.000 claims description 92
• 238000000034 method Methods 0.000 claims description 85
• 208000015181 infectious disease Diseases 0.000 claims description 42
• 229910052799 carbon Inorganic materials 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 34
• 125000000217 alkyl group Chemical class 0.000 claims description 29
• 125000003342 alkenyl group Chemical group 0.000 claims description 28
• 125000000304 alkynyl group Chemical group 0.000 claims description 28
• 125000004429 atom Chemical group 0.000 claims description 27
• 239000000651 prodrug Substances 0.000 claims description 23
• 229940002612 prodrug Drugs 0.000 claims description 23
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
• 241000251468 Actinopterygii Species 0.000 claims description 15
• 241000124008 Mammalia Species 0.000 claims description 15
• 238000011282 treatment Methods 0.000 claims description 15
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 14
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
• 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 14
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 125000004122 cyclic group Chemical group 0.000 claims description 13
• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 12
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• 239000012453 solvate Substances 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 229910052786 argon Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 6
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 229910052705 radium Inorganic materials 0.000 claims description 4
• 229910052701 rubidium Inorganic materials 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 3
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
• 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 claims description 2
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 3
• 125000001589 carboacyl group Chemical group 0.000 claims 1
• 108010030975 Polyketide Synthases Proteins 0.000 description 80
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Natural products O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 76
• 238000011068 loading method Methods 0.000 description 55
• 108090000623 proteins and genes Proteins 0.000 description 50
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• 229960003276 erythromycin Drugs 0.000 description 42
• 238000006243 chemical reaction Methods 0.000 description 39
• 239000000203 mixture Substances 0.000 description 38
• 230000015572 biosynthetic process Effects 0.000 description 33
• 239000007858 starting material Substances 0.000 description 33
• 238000003786 synthesis reaction Methods 0.000 description 26
• 229930001119 polyketide Natural products 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 239000002585 base Substances 0.000 description 23
• 238000012360 testing method Methods 0.000 description 23
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 22
• 208000035143 Bacterial infection Diseases 0.000 description 22
• 208000010362 Protozoan Infections Diseases 0.000 description 22
• 208000022362 bacterial infectious disease Diseases 0.000 description 22
• 239000000047 product Substances 0.000 description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 239000002253 acid Substances 0.000 description 21
• 239000003120 macrolide antibiotic agent Substances 0.000 description 21
• 125000000830 polyketide group Chemical group 0.000 description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 16
• 238000004519 manufacturing process Methods 0.000 description 16
• 239000011541 reaction mixture Substances 0.000 description 16
• 239000000243 solution Substances 0.000 description 16
• 210000004027 cell Anatomy 0.000 description 15
• 208000035475 disorder Diseases 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• 230000001580 bacterial effect Effects 0.000 description 14
• 238000002360 preparation method Methods 0.000 description 14
• 239000007787 solid Substances 0.000 description 14
• 239000003242 anti bacterial agent Substances 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 108020004414 DNA Proteins 0.000 description 12
• 239000001257 hydrogen Substances 0.000 description 12
• 230000009467 reduction Effects 0.000 description 12
• 230000029936 alkylation Effects 0.000 description 11
• 238000005804 alkylation reaction Methods 0.000 description 11
• 241000606856 Pasteurella multocida Species 0.000 description 10
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 10
• 239000003153 chemical reaction reagent Substances 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 239000008194 pharmaceutical composition Substances 0.000 description 10
• 238000006722 reduction reaction Methods 0.000 description 10
• 238000005932 reductive alkylation reaction Methods 0.000 description 10
• 241000271566 Aves Species 0.000 description 9
• 206010061218 Inflammation Diseases 0.000 description 9
• 241001465754 Metazoa Species 0.000 description 9
• 239000007832 Na2SO4 Substances 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
• 150000002148 esters Chemical class 0.000 description 9
• 238000000855 fermentation Methods 0.000 description 9
• 230000004151 fermentation Effects 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 230000004054 inflammatory process Effects 0.000 description 9
• 125000006239 protecting group Chemical group 0.000 description 9
• 229910052938 sodium sulfate Inorganic materials 0.000 description 9
• 235000011152 sodium sulphate Nutrition 0.000 description 9
• 239000005660 Abamectin Substances 0.000 description 8
• 241000283690 Bos taurus Species 0.000 description 8
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 230000000844 anti-bacterial effect Effects 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 8
• AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical class O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 8
• 238000007796 conventional method Methods 0.000 description 8
• 238000005516 engineering process Methods 0.000 description 8
• 229940041033 macrolides Drugs 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 239000013612 plasmid Substances 0.000 description 8
• 150000003881 polyketide derivatives Chemical class 0.000 description 8
• 230000008569 process Effects 0.000 description 8
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 8
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 8
• 229960002930 sirolimus Drugs 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• 101710146995 Acyl carrier protein Proteins 0.000 description 7
• 241000187432 Streptomyces coelicolor Species 0.000 description 7
• 229940088710 antibiotic agent Drugs 0.000 description 7
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
• 239000003085 diluting agent Substances 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
• 239000003937 drug carrier Substances 0.000 description 7
• 150000002431 hydrogen Chemical class 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• ACTOXUHEUCPTEW-BWHGAVFKSA-N 2-[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2s,5s,6r)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-o Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)[C@@H]1CC[C@H](N(C)C)[C@@H](C)O1 ACTOXUHEUCPTEW-BWHGAVFKSA-N 0.000 description 6
• 241000894006 Bacteria Species 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• 241001293418 Mannheimia haemolytica Species 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• 241000187559 Saccharopolyspora erythraea Species 0.000 description 6
• 239000004187 Spiramycin Substances 0.000 description 6
• 241000193996 Streptococcus pyogenes Species 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• 230000009471 action Effects 0.000 description 6
• 239000012190 activator Substances 0.000 description 6
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 6
• 238000010276 construction Methods 0.000 description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
• 125000005843 halogen group Chemical group 0.000 description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• 231100000252 nontoxic Toxicity 0.000 description 6
• 230000003000 nontoxic effect Effects 0.000 description 6
• 150000002923 oximes Chemical group 0.000 description 6
• 229920001184 polypeptide Chemical group 0.000 description 6
• 108090000765 processed proteins & peptides Chemical group 0.000 description 6
• 102000004196 processed proteins & peptides Human genes 0.000 description 6
• 229960001294 spiramycin Drugs 0.000 description 6
• 235000019372 spiramycin Nutrition 0.000 description 6
• 229930191512 spiramycin Natural products 0.000 description 6
• 230000001225 therapeutic effect Effects 0.000 description 6
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• 102000004190 Enzymes Human genes 0.000 description 5
• 241000282414 Homo sapiens Species 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
• 241000699670 Mus sp. Species 0.000 description 5
• 239000004104 Oleandomycin Substances 0.000 description 5
• RZPAKFUAFGMUPI-UHFFFAOYSA-N Oleandomycin Natural products O1C(C)C(O)C(OC)CC1OC1C(C)C(=O)OC(C)C(C)C(O)C(C)C(=O)C2(OC2)CC(C)C(OC2C(C(CC(C)O2)N(C)C)O)C1C RZPAKFUAFGMUPI-UHFFFAOYSA-N 0.000 description 5
• 150000001447 alkali salts Chemical class 0.000 description 5
• 239000003904 antiprotozoal agent Substances 0.000 description 5
• 150000007514 bases Chemical class 0.000 description 5
• 150000001732 carboxylic acid derivatives Chemical group 0.000 description 5
• 238000007385 chemical modification Methods 0.000 description 5
• 239000002552 dosage form Substances 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 150000002118 epoxides Chemical group 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 229960002351 oleandomycin Drugs 0.000 description 5
• RZPAKFUAFGMUPI-KGIGTXTPSA-N oleandomycin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C RZPAKFUAFGMUPI-KGIGTXTPSA-N 0.000 description 5
• 235000019367 oleandomycin Nutrition 0.000 description 5
• 238000007254 oxidation reaction Methods 0.000 description 5
• 239000000546 pharmaceutical excipient Substances 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 5
• XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 4
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
• 238000006237 Beckmann rearrangement reaction Methods 0.000 description 4
• 241000588724 Escherichia coli Species 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 229960000583 acetic acid Drugs 0.000 description 4
• ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 4
• 125000002252 acyl group Chemical group 0.000 description 4
• 238000005917 acylation reaction Methods 0.000 description 4
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
• 150000001540 azides Chemical class 0.000 description 4
• 230000003115 biocidal effect Effects 0.000 description 4
• 150000001768 cations Chemical class 0.000 description 4
• 210000000349 chromosome Anatomy 0.000 description 4
• 239000002270 dispersing agent Substances 0.000 description 4
• 235000019256 formaldehyde Nutrition 0.000 description 4
• 235000019253 formic acid Nutrition 0.000 description 4
• 125000000524 functional group Chemical group 0.000 description 4
• 230000002140 halogenating effect Effects 0.000 description 4
• 150000007522 mineralic acids Chemical class 0.000 description 4
• 150000007524 organic acids Chemical class 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 230000003647 oxidation Effects 0.000 description 4
• 230000037361 pathway Effects 0.000 description 4
• 238000003752 polymerase chain reaction Methods 0.000 description 4
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 230000002829 reductive effect Effects 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• 238000013207 serial dilution Methods 0.000 description 4
• 238000007920 subcutaneous administration Methods 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• 230000000699 topical effect Effects 0.000 description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• YHVUVJYEERGYNU-UHFFFAOYSA-N 4',8-Di-Me ether-5,7,8-Trihydroxy-3-(4-hydroxybenzyl)-4-chromanone Natural products COC1(C)CC(O)OC(C)C1O YHVUVJYEERGYNU-UHFFFAOYSA-N 0.000 description 3
• 229920001817 Agar Polymers 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• 241000282472 Canis lupus familiaris Species 0.000 description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
• 241000193403 Clostridium Species 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• 241000282326 Felis catus Species 0.000 description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
• 241000606768 Haemophilus influenzae Species 0.000 description 3
• 241000282412 Homo Species 0.000 description 3
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
• 229930191564 Monensin Natural products 0.000 description 3
• GAOZTHIDHYLHMS-UHFFFAOYSA-N Monensin A Natural products O1C(CC)(C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CCC1C(O1)(C)CCC21CC(O)C(C)C(C(C)C(OC)C(C)C(O)=O)O2 GAOZTHIDHYLHMS-UHFFFAOYSA-N 0.000 description 3
• 108091028043 Nucleic acid sequence Proteins 0.000 description 3
• 229910019142 PO4 Inorganic materials 0.000 description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• 241000191967 Staphylococcus aureus Species 0.000 description 3
• 241000191963 Staphylococcus epidermidis Species 0.000 description 3
• 241000187747 Streptomyces Species 0.000 description 3
• 239000004182 Tylosin Substances 0.000 description 3
• 229930194936 Tylosin Natural products 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
• VTIKDEXOEJDMJP-WYUUTHIRSA-N actinorhodin Chemical compound C([C@@H](CC(O)=O)O[C@@H]1C)C(C(C2=C(O)C=3)=O)=C1C(=O)C2=C(O)C=3C(C(=C1C2=O)O)=CC(O)=C1C(=O)C1=C2[C@@H](C)O[C@H](CC(O)=O)C1 VTIKDEXOEJDMJP-WYUUTHIRSA-N 0.000 description 3
• 230000010933 acylation Effects 0.000 description 3
• 239000008272 agar Substances 0.000 description 3
• 229910052783 alkali metal Inorganic materials 0.000 description 3
• RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 235000001014 amino acid Nutrition 0.000 description 3
• 125000000539 amino acid group Chemical group 0.000 description 3
• 150000001413 amino acids Chemical class 0.000 description 3
• 238000000429 assembly Methods 0.000 description 3
• 230000000712 assembly Effects 0.000 description 3
• 238000004587 chromatography analysis Methods 0.000 description 3
• 238000002648 combination therapy Methods 0.000 description 3
• 235000014113 dietary fatty acids Nutrition 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 238000006345 epimerization reaction Methods 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 239000000194 fatty acid Substances 0.000 description 3
• 229930195729 fatty acid Natural products 0.000 description 3
• 150000004665 fatty acids Chemical class 0.000 description 3
• 239000011737 fluorine Substances 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 108091008053 gene clusters Proteins 0.000 description 3
• 230000014509 gene expression Effects 0.000 description 3
• 230000012010 growth Effects 0.000 description 3
• 238000001727 in vivo Methods 0.000 description 3
• 238000001802 infusion Methods 0.000 description 3
• 239000010410 layer Substances 0.000 description 3
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
• 230000004048 modification Effects 0.000 description 3
• 238000012986 modification Methods 0.000 description 3
• 229960005358 monensin Drugs 0.000 description 3
• GAOZTHIDHYLHMS-KEOBGNEYSA-N monensin A Chemical compound C([C@@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O2 GAOZTHIDHYLHMS-KEOBGNEYSA-N 0.000 description 3
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
• 239000010452 phosphate Substances 0.000 description 3
• 229920001223 polyethylene glycol Polymers 0.000 description 3
• 102000004169 proteins and genes Human genes 0.000 description 3
• 230000008261 resistance mechanism Effects 0.000 description 3
• 238000009097 single-agent therapy Methods 0.000 description 3
• 239000000758 substrate Substances 0.000 description 3
• 239000000375 suspending agent Substances 0.000 description 3
• WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 3
• 229960004059 tylosin Drugs 0.000 description 3
• 235000019375 tylosin Nutrition 0.000 description 3
• 239000013598 vector Substances 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
• 241000186361 Actinobacteria <class> Species 0.000 description 2
• VTIKDEXOEJDMJP-UHFFFAOYSA-N Actinorhodine Natural products CC1OC(CC(=O)O)CC2=C1C(=O)c3c(O)c(cc(O)c3C2=O)c4cc(O)c5C(=O)C6=C(C(C)OC(CC(=O)O)C6)C(=O)c5c4O VTIKDEXOEJDMJP-UHFFFAOYSA-N 0.000 description 2
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 241001148536 Bacteroides sp. Species 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 241001647372 Chlamydia pneumoniae Species 0.000 description 2
• 241000606153 Chlamydia trachomatis Species 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
• 101710095468 Cyclase Proteins 0.000 description 2
• 241000194033 Enterococcus Species 0.000 description 2
• 241000194032 Enterococcus faecalis Species 0.000 description 2
• 241000194031 Enterococcus faecium Species 0.000 description 2
• 230000005526 G1 to G0 transition Effects 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
• 239000002841 Lewis acid Substances 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
• DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 2
• 108700026244 Open Reading Frames Proteins 0.000 description 2
• 241000191992 Peptostreptococcus Species 0.000 description 2
• 201000005702 Pertussis Diseases 0.000 description 2
• 239000004721 Polyphenylene oxide Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• 102100029437 Serine/threonine-protein kinase A-Raf Human genes 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
• 206010062255 Soft tissue infection Diseases 0.000 description 2
• 241000295644 Staphylococcaceae Species 0.000 description 2
• 241000193998 Streptococcus pneumoniae Species 0.000 description 2
• 241000186988 Streptomyces antibioticus Species 0.000 description 2
• 241001468227 Streptomyces avermitilis Species 0.000 description 2
• QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 2
• 239000004098 Tetracycline Substances 0.000 description 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
• 108091006088 activator proteins Proteins 0.000 description 2
• 239000004480 active ingredient Substances 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• 125000004423 acyloxy group Chemical group 0.000 description 2
• 229910052784 alkaline earth metal Chemical class 0.000 description 2
• 125000005907 alkyl ester group Chemical group 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 125000003277 amino group Chemical group 0.000 description 2
• 230000003698 anagen phase Effects 0.000 description 2
• 230000000842 anti-protozoal effect Effects 0.000 description 2
• 238000011203 antimicrobial therapy Methods 0.000 description 2
• 238000013459 approach Methods 0.000 description 2
• 239000007900 aqueous suspension Substances 0.000 description 2
• 239000012298 atmosphere Substances 0.000 description 2
• 125000002393 azetidinyl group Chemical group 0.000 description 2
• 244000052616 bacterial pathogen Species 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
• 238000007068 beta-elimination reaction Methods 0.000 description 2
• 230000002457 bidirectional effect Effects 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 125000004432 carbon atom Chemical group C* 0.000 description 2
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
• 239000001768 carboxy methyl cellulose Substances 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 238000010531 catalytic reduction reaction Methods 0.000 description 2
• 239000003638 chemical reducing agent Substances 0.000 description 2
• 239000000460 chlorine Substances 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 238000003776 cleavage reaction Methods 0.000 description 2
• 238000009833 condensation Methods 0.000 description 2
• 230000005494 condensation Effects 0.000 description 2
• 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 2
• 238000006114 decarboxylation reaction Methods 0.000 description 2
• 238000010790 dilution Methods 0.000 description 2
• 239000012895 dilution Substances 0.000 description 2
• 201000010099 disease Diseases 0.000 description 2
• 239000012039 electrophile Substances 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 230000029142 excretion Effects 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 238000011049 filling Methods 0.000 description 2
• 235000019867 fractionated palm kernal oil Nutrition 0.000 description 2
• 239000012458 free base Substances 0.000 description 2
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
• 239000007903 gelatin capsule Substances 0.000 description 2
• 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 description 2
• 125000005456 glyceride group Chemical group 0.000 description 2
• 229940047650 haemophilus influenzae Drugs 0.000 description 2
• UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
• 238000004128 high performance liquid chromatography Methods 0.000 description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
• 125000002883 imidazolyl group Chemical group 0.000 description 2
• 230000002458 infectious effect Effects 0.000 description 2
• 230000002401 inhibitory effect Effects 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 230000010354 integration Effects 0.000 description 2
• 208000028774 intestinal disease Diseases 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• 238000007912 intraperitoneal administration Methods 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• 239000002555 ionophore Substances 0.000 description 2
• 230000000236 ionophoric effect Effects 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• 150000007517 lewis acids Chemical class 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• 229930013918 macrolide polyketide Natural products 0.000 description 2
• 125000000585 macrolide polyketide group Chemical group 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 230000007246 mechanism Effects 0.000 description 2
• 239000002609 medium Substances 0.000 description 2
• 229910052987 metal hydride Inorganic materials 0.000 description 2
• 150000004681 metal hydrides Chemical class 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• 239000002480 mineral oil Substances 0.000 description 2
• 235000010446 mineral oil Nutrition 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• 238000012544 monitoring process Methods 0.000 description 2
• 239000012044 organic layer Substances 0.000 description 2
• 230000008520 organization Effects 0.000 description 2
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
• 244000052769 pathogen Species 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• 239000013600 plasmid vector Substances 0.000 description 2
• 229910003446 platinum oxide Inorganic materials 0.000 description 2
• 229920000570 polyether Polymers 0.000 description 2
• 229920000642 polymer Polymers 0.000 description 2
• 229920000136 polysorbate Polymers 0.000 description 2
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
• 229910000105 potassium hydride Inorganic materials 0.000 description 2
• 159000000001 potassium salts Chemical class 0.000 description 2
• ZMJJCODMIXQWCQ-UHFFFAOYSA-N potassium;di(propan-2-yl)azanide Chemical compound [K+].CC(C)[N-]C(C)C ZMJJCODMIXQWCQ-UHFFFAOYSA-N 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 238000012545 processing Methods 0.000 description 2
• 230000000069 prophylactic effect Effects 0.000 description 2
• QAQREVBBADEHPA-IEXPHMLFSA-N propionyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 QAQREVBBADEHPA-IEXPHMLFSA-N 0.000 description 2
• 235000018102 proteins Nutrition 0.000 description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
• 150000003254 radicals Chemical class 0.000 description 2
• 230000003252 repetitive effect Effects 0.000 description 2
• 208000023504 respiratory system disease Diseases 0.000 description 2
• 230000007017 scission Effects 0.000 description 2
• 206010040872 skin infection Diseases 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 239000012279 sodium borohydride Substances 0.000 description 2
• 229910000033 sodium borohydride Inorganic materials 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 229910000104 sodium hydride Inorganic materials 0.000 description 2
• 238000000638 solvent extraction Methods 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• 239000004094 surface-active agent Substances 0.000 description 2
• 208000024891 symptom Diseases 0.000 description 2
• 239000003826 tablet Substances 0.000 description 2
• QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 2
• 229960002180 tetracycline Drugs 0.000 description 2
• 235000019364 tetracycline Nutrition 0.000 description 2
• 229930101283 tetracycline Natural products 0.000 description 2
• 150000003522 tetracyclines Chemical class 0.000 description 2
• 229940124597 therapeutic agent Drugs 0.000 description 2
• 238000002560 therapeutic procedure Methods 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 238000013518 transcription Methods 0.000 description 2
• 230000035897 transcription Effects 0.000 description 2
• 230000007704 transition Effects 0.000 description 2
• SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 2
• 208000019206 urinary tract infection Diseases 0.000 description 2
• 239000000341 volatile oil Substances 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
• GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
• 101150084750 1 gene Proteins 0.000 description 1
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 1
• CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
• LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• PTPROPUVXIZJPL-UHFFFAOYSA-N 3,4-dihydroxycyclohexane-1-carboxylic acid Chemical compound OC1CCC(C(O)=O)CC1O PTPROPUVXIZJPL-UHFFFAOYSA-N 0.000 description 1
• BRMWTNUJHUMWMS-UHFFFAOYSA-N 3-Methylhistidine Natural products CN1C=NC(CC(N)C(O)=O)=C1 BRMWTNUJHUMWMS-UHFFFAOYSA-N 0.000 description 1
• 108010019608 3-Oxoacyl-(Acyl-Carrier-Protein) Synthase Proteins 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
• 102100037149 3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrial Human genes 0.000 description 1
• 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 description 1
• 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
• 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
• ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
• HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• 241000606750 Actinobacillus Species 0.000 description 1
• 108700037654 Acyl carrier protein (ACP) Proteins 0.000 description 1
• 102000048456 Acyl carrier protein (ACP) Human genes 0.000 description 1
• 241000588986 Alcaligenes Species 0.000 description 1
• 229930183010 Amphotericin Natural products 0.000 description 1
• QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• 241001518086 Bartonella henselae Species 0.000 description 1
• 102000011802 Beta-ketoacyl synthases Human genes 0.000 description 1
• 108050002233 Beta-ketoacyl synthases Proteins 0.000 description 1
• 102000004506 Blood Proteins Human genes 0.000 description 1
• 108010017384 Blood Proteins Proteins 0.000 description 1
• 241000588807 Bordetella Species 0.000 description 1
• 241000180135 Borrelia recurrentis Species 0.000 description 1
• 241000589969 Borreliella burgdorferi Species 0.000 description 1
• 241000589893 Brachyspira hyodysenteriae Species 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• 206010051226 Campylobacter infection Diseases 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
• 101710134389 Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 2 Proteins 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 208000024172 Cardiovascular disease Diseases 0.000 description 1
• 241000193468 Clostridium perfringens Species 0.000 description 1
• 108010065152 Coagulase Proteins 0.000 description 1
• 241000224483 Coccidia Species 0.000 description 1
• 244000060011 Cocos nucifera Species 0.000 description 1
• 235000013162 Cocos nucifera Nutrition 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 241000186216 Corynebacterium Species 0.000 description 1
• 241000186227 Corynebacterium diphtheriae Species 0.000 description 1
• 241001518260 Corynebacterium minutissimum Species 0.000 description 1
• 241000223935 Cryptosporidium Species 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 241000605721 Dichelobacter nodosus Species 0.000 description 1
• 241000792859 Enema Species 0.000 description 1
• 241000588914 Enterobacter Species 0.000 description 1
• 241000520130 Enterococcus durans Species 0.000 description 1
• 101100119095 Enterococcus faecalis (strain ATCC 700802 / V583) ermB gene Proteins 0.000 description 1
• 229930006677 Erythromycin A Natural products 0.000 description 1
• IDRYSCOQVVUBIJ-UHFFFAOYSA-N Erythromycin-B Natural products CC1C(OC2C(C(CC(C)O2)N(C)C)O)C(C)(O)CC(C)C(=O)C(C)C(O)C(C)C(CC)OC(=O)C(C)C1OC1CC(C)(OC)C(O)C(C)O1 IDRYSCOQVVUBIJ-UHFFFAOYSA-N 0.000 description 1
• 108090000371 Esterases Proteins 0.000 description 1
• 241000186394 Eubacterium Species 0.000 description 1
• 206010015943 Eye inflammation Diseases 0.000 description 1
• 239000004606 Fillers/Extenders Substances 0.000 description 1
• 206010016952 Food poisoning Diseases 0.000 description 1
• 208000019331 Foodborne disease Diseases 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
• 241000605909 Fusobacterium Species 0.000 description 1
• 241000605952 Fusobacterium necrophorum Species 0.000 description 1
• 201000000628 Gas Gangrene Diseases 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• 108700039691 Genetic Promoter Regions Proteins 0.000 description 1
• 206010018364 Glomerulonephritis Diseases 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 206010019375 Helicobacter infections Diseases 0.000 description 1
• 241000590002 Helicobacter pylori Species 0.000 description 1
• 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
• 101000601394 Homo sapiens Neuroendocrine convertase 2 Proteins 0.000 description 1
• 102000008100 Human Serum Albumin Human genes 0.000 description 1
• 108091006905 Human Serum Albumin Proteins 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 description 1
• PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
• 238000012404 In vitro experiment Methods 0.000 description 1
• 101150111320 KS gene Proteins 0.000 description 1
• 241000588748 Klebsiella Species 0.000 description 1
• SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
• AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
• RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
• UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 1
• UCUNFLYVYCGDHP-BYPYZUCNSA-N L-methionine sulfone Chemical compound CS(=O)(=O)CC[C@H](N)C(O)=O UCUNFLYVYCGDHP-BYPYZUCNSA-N 0.000 description 1
• SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• 239000004166 Lanolin Substances 0.000 description 1
• 241001148567 Lawsonia intracellularis Species 0.000 description 1
• 241000589242 Legionella pneumophila Species 0.000 description 1
• 101001110310 Lentilactobacillus kefiri NADP-dependent (R)-specific alcohol dehydrogenase Proteins 0.000 description 1
• 241000186781 Listeria Species 0.000 description 1
• 208000016604 Lyme disease Diseases 0.000 description 1
• 101150052154 MSRA1 gene Proteins 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 208000010315 Mastoiditis Diseases 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 241000187723 Micromonospora sp. Species 0.000 description 1
• 101001014220 Monascus pilosus Dehydrogenase mokE Proteins 0.000 description 1
• 241000588622 Moraxella bovis Species 0.000 description 1
• 241000588655 Moraxella catarrhalis Species 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 241000186367 Mycobacterium avium Species 0.000 description 1
• 241000513886 Mycobacterium avium complex (MAC) Species 0.000 description 1
• 241000187482 Mycobacterium avium subsp. paratuberculosis Species 0.000 description 1
• 241000187478 Mycobacterium chelonae Species 0.000 description 1
• 241000186364 Mycobacterium intracellulare Species 0.000 description 1
• 241000186363 Mycobacterium kansasii Species 0.000 description 1
• 241000186362 Mycobacterium leprae Species 0.000 description 1
• 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
• 241000204031 Mycoplasma Species 0.000 description 1
• 241001138504 Mycoplasma bovis Species 0.000 description 1
• 241000202934 Mycoplasma pneumoniae Species 0.000 description 1
• JDHILDINMRGULE-LURJTMIESA-N N(pros)-methyl-L-histidine Chemical compound CN1C=NC=C1C[C@H](N)C(O)=O JDHILDINMRGULE-LURJTMIESA-N 0.000 description 1
• FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical class CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
• 241000588652 Neisseria gonorrhoeae Species 0.000 description 1
• 102100037732 Neuroendocrine convertase 2 Human genes 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• 241000187681 Nocardia sp. Species 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 206010048685 Oral infection Diseases 0.000 description 1
• AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
• UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
• 206010031252 Osteomyelitis Diseases 0.000 description 1
• 206010033078 Otitis media Diseases 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 101000573542 Penicillium citrinum Compactin nonaketide synthase, enoyl reductase component Proteins 0.000 description 1
• 238000005835 Pfitzner-Moffat oxidation reaction Methods 0.000 description 1
• 201000007100 Pharyngitis Diseases 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• 206010035664 Pneumonia Diseases 0.000 description 1
• 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 229920001214 Polysorbate 60 Polymers 0.000 description 1
• 241000605894 Porphyromonas Species 0.000 description 1
• 241000605861 Prevotella Species 0.000 description 1
• 102000007327 Protamines Human genes 0.000 description 1
• 108010007568 Protamines Proteins 0.000 description 1
• 102000055027 Protein Methyltransferases Human genes 0.000 description 1
• 108700040121 Protein Methyltransferases Proteins 0.000 description 1
• 206010037660 Pyrexia Diseases 0.000 description 1
• 108020004511 Recombinant DNA Proteins 0.000 description 1
• 229930189077 Rifamycin Natural products 0.000 description 1
• 241000187560 Saccharopolyspora Species 0.000 description 1
• 241001468199 Saccharopolyspora sp. Species 0.000 description 1
• 241000607142 Salmonella Species 0.000 description 1
• 206010040070 Septic Shock Diseases 0.000 description 1
• 208000019802 Sexually transmitted disease Diseases 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
• 241000191980 Staphylococcus intermedius Species 0.000 description 1
• 241001147691 Staphylococcus saprophyticus Species 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 102100021588 Sterol carrier protein 2 Human genes 0.000 description 1
• 241000193985 Streptococcus agalactiae Species 0.000 description 1
• 241000194042 Streptococcus dysgalactiae Species 0.000 description 1
• 241001312524 Streptococcus viridans Species 0.000 description 1
• 108010015795 Streptogramin B Proteins 0.000 description 1
• 108010034396 Streptogramins Proteins 0.000 description 1
• 241000187758 Streptomyces ambofaciens Species 0.000 description 1
• 241001509463 Streptomyces caelestis Species 0.000 description 1
• 241000187434 Streptomyces cinnamonensis Species 0.000 description 1
• 101100161930 Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145) actIII gene Proteins 0.000 description 1
• 241000187438 Streptomyces fradiae Species 0.000 description 1
• 241000936710 Streptomyces griseoplanus Species 0.000 description 1
• 241000187391 Streptomyces hygroscopicus Species 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 241000282898 Sus scrofa Species 0.000 description 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
• 102000005488 Thioesterase Human genes 0.000 description 1
• 229910010062 TiCl3 Inorganic materials 0.000 description 1
• 206010044248 Toxic shock syndrome Diseases 0.000 description 1
• 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
• 206010044302 Tracheitis Diseases 0.000 description 1
• 241000589884 Treponema pallidum Species 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• 241000202921 Ureaplasma urealyticum Species 0.000 description 1
• 206010046793 Uterine inflammation Diseases 0.000 description 1
• 108010059993 Vancomycin Proteins 0.000 description 1
• SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
• 241000606834 [Haemophilus] ducreyi Species 0.000 description 1
• 206010000210 abortion Diseases 0.000 description 1
• 231100000176 abortion Toxicity 0.000 description 1
• 229940124532 absorption promoter Drugs 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 238000012382 advanced drug delivery Methods 0.000 description 1
• 238000002814 agar dilution Methods 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
• 229940024548 aluminum oxide Drugs 0.000 description 1
• 229940063655 aluminum stearate Drugs 0.000 description 1
• 125000003368 amide group Chemical group 0.000 description 1
• 229940126575 aminoglycoside Drugs 0.000 description 1
• 229940009444 amphotericin Drugs 0.000 description 1
• APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
• PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
• 230000000845 anti-microbial effect Effects 0.000 description 1
• 239000004599 antimicrobial Substances 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• 150000001491 aromatic compounds Chemical class 0.000 description 1
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
• 150000005840 aryl radicals Chemical class 0.000 description 1
• ZDQSOHOQTUFQEM-PKUCKEGBSA-N ascomycin Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C\C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 ZDQSOHOQTUFQEM-PKUCKEGBSA-N 0.000 description 1
• ZDQSOHOQTUFQEM-XCXYXIJFSA-N ascomycin Natural products CC[C@H]1C=C(C)C[C@@H](C)C[C@@H](OC)[C@H]2O[C@@](O)([C@@H](C)C[C@H]2OC)C(=O)C(=O)N3CCCC[C@@H]3C(=O)O[C@H]([C@H](C)[C@@H](O)CC1=O)C(=C[C@@H]4CC[C@@H](O)[C@H](C4)OC)C ZDQSOHOQTUFQEM-XCXYXIJFSA-N 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 101150036080 at gene Proteins 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
• 125000003828 azulenyl group Chemical group 0.000 description 1
• 229940092524 bartonella henselae Drugs 0.000 description 1
• 235000013871 bee wax Nutrition 0.000 description 1
• 239000012166 beeswax Substances 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 235000019445 benzyl alcohol Nutrition 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 229940000635 beta-alanine Drugs 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 230000001851 biosynthetic effect Effects 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• 239000012267 brine Substances 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 235000014121 butter Nutrition 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 210000004899 c-terminal region Anatomy 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 235000013877 carbamide Nutrition 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 125000002843 carboxylic acid group Chemical group 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 239000012876 carrier material Substances 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 235000019438 castor oil Nutrition 0.000 description 1
• 239000006285 cell suspension Substances 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 210000003679 cervix uteri Anatomy 0.000 description 1
• 229940081733 cetearyl alcohol Drugs 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 125000003636 chemical group Chemical group 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 229960005091 chloramphenicol Drugs 0.000 description 1
• WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 229940001468 citrate Drugs 0.000 description 1
• 229960002173 citrulline Drugs 0.000 description 1
• 235000013477 citrulline Nutrition 0.000 description 1
• 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
• 230000001332 colony forming effect Effects 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 210000000795 conjunctiva Anatomy 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 210000004087 cornea Anatomy 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 201000010251 cutis laxa Diseases 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 235000013365 dairy product Nutrition 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• 230000018044 dehydration Effects 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• 238000012217 deletion Methods 0.000 description 1
• 230000037430 deletion Effects 0.000 description 1
• YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
• 238000003386 deoximation reaction Methods 0.000 description 1
• 238000010511 deprotection reaction Methods 0.000 description 1
• 238000009795 derivation Methods 0.000 description 1
• 238000001212 derivatisation Methods 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• 210000002249 digestive system Anatomy 0.000 description 1
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
• GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
• GZRYBYIBLHMWCD-UHFFFAOYSA-N dimethyl(methylidene)-$l^{4}-sulfane Chemical compound CS(C)=C GZRYBYIBLHMWCD-UHFFFAOYSA-N 0.000 description 1
• DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
• 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
• 235000019797 dipotassium phosphate Nutrition 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000006073 displacement reaction Methods 0.000 description 1
• 125000005883 dithianyl group Chemical group 0.000 description 1
• 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 description 1
• PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
• 238000012377 drug delivery Methods 0.000 description 1
• 239000003792 electrolyte Substances 0.000 description 1
• 239000008387 emulsifying waxe Substances 0.000 description 1
• 206010014665 endocarditis Diseases 0.000 description 1
• 239000007920 enema Substances 0.000 description 1
• 229940095399 enema Drugs 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 229940032049 enterococcus faecalis Drugs 0.000 description 1
• 101150016744 ermC gene Proteins 0.000 description 1
• YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 1
• IDRYSCOQVVUBIJ-PPGFLMPOSA-N erythromycin B Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@H]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)C)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 IDRYSCOQVVUBIJ-PPGFLMPOSA-N 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
• 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 125000003838 furazanyl group Chemical group 0.000 description 1
• 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 238000010353 genetic engineering Methods 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 229930195712 glutamate Natural products 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
• 229960002449 glycine Drugs 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 230000003862 health status Effects 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
• 230000006801 homologous recombination Effects 0.000 description 1
• 238000002744 homologous recombination Methods 0.000 description 1
• 210000000003 hoof Anatomy 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
• 229960002591 hydroxyproline Drugs 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 230000001506 immunosuppresive effect Effects 0.000 description 1
• 230000006872 improvement Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• 230000002779 inactivation Effects 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000000977 initiatory effect Effects 0.000 description 1
• 229940102223 injectable solution Drugs 0.000 description 1
• 229940102213 injectable suspension Drugs 0.000 description 1
• 238000011081 inoculation Methods 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 230000000968 intestinal effect Effects 0.000 description 1
• 238000007917 intracranial administration Methods 0.000 description 1
• 238000007919 intrasynovial administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 150000002596 lactones Chemical class 0.000 description 1
• 235000019388 lanolin Nutrition 0.000 description 1
• 229940039717 lanolin Drugs 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 229940115932 legionella pneumophila Drugs 0.000 description 1
• 125000005647 linker group Chemical group 0.000 description 1
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000000391 magnesium silicate Substances 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 229940099273 magnesium trisilicate Drugs 0.000 description 1
• 235000019793 magnesium trisilicate Nutrition 0.000 description 1
• 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 101150111763 mefA gene Proteins 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 230000011987 methylation Effects 0.000 description 1
• 238000007069 methylation reaction Methods 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical group OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
• MZFOKIKEPGUZEN-FBMOWMAESA-N methylmalonyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C(C(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MZFOKIKEPGUZEN-FBMOWMAESA-N 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 229940042472 mineral oil Drugs 0.000 description 1
• 238000003032 molecular docking Methods 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 101150021123 msrA gene Proteins 0.000 description 1
• 101150114366 msrA2 gene Proteins 0.000 description 1
• 101150006794 msrAB gene Proteins 0.000 description 1
• 101150109310 msrAB1 gene Proteins 0.000 description 1
• 101150052209 msrAB2 gene Proteins 0.000 description 1
• 210000004400 mucous membrane Anatomy 0.000 description 1
• 230000035772 mutation Effects 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 239000007922 nasal spray Substances 0.000 description 1
• 229930014626 natural product Natural products 0.000 description 1
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• 108020004707 nucleic acids Proteins 0.000 description 1
• 150000007523 nucleic acids Chemical class 0.000 description 1
• 102000039446 nucleic acids Human genes 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
• 239000003921 oil Substances 0.000 description 1
• 235000019198 oils Nutrition 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 239000004006 olive oil Substances 0.000 description 1
• 235000008390 olive oil Nutrition 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 229960003104 ornithine Drugs 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000003551 oxepanyl group Chemical group 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical class C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
• 229940014662 pantothenate Drugs 0.000 description 1
• 235000019161 pantothenic acid Nutrition 0.000 description 1
• 239000011713 pantothenic acid Substances 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 235000019271 petrolatum Nutrition 0.000 description 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
• 150000003014 phosphoric acid esters Chemical class 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• 230000026731 phosphorylation Effects 0.000 description 1
• 238000006366 phosphorylation reaction Methods 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 239000000049 pigment Substances 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 229920000058 polyacrylate Polymers 0.000 description 1
• 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
• 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
• 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
• 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
• 229940113124 polysorbate 60 Drugs 0.000 description 1
• 229920000053 polysorbate 80 Polymers 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 235000010241 potassium sorbate Nutrition 0.000 description 1
• 239000004302 potassium sorbate Substances 0.000 description 1
• 229940069338 potassium sorbate Drugs 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 230000002028 premature Effects 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• YGXCETJZBDTKRY-DZCVGBHJSA-N pristinamycin IA Chemical compound N([C@@H]1C(=O)N[C@@H](C(N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(=CC=2)N(C)C)C(=O)N2CCC(=O)C[C@H]2C(=O)N[C@H](C(=O)O[C@@H]1C)C=1C=CC=CC=1)=O)CC)C(=O)C1=NC=CC=C1O YGXCETJZBDTKRY-DZCVGBHJSA-N 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229950008679 protamine sulfate Drugs 0.000 description 1
• 244000079416 protozoan pathogen Species 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 230000002285 radioactive effect Effects 0.000 description 1
• 238000009790 rate-determining step (RDS) Methods 0.000 description 1
• 229940100618 rectal suppository Drugs 0.000 description 1
• 239000006215 rectal suppository Substances 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 210000002345 respiratory system Anatomy 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 201000003068 rheumatic fever Diseases 0.000 description 1
• 229960003292 rifamycin Drugs 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 238000012163 sequencing technique Methods 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
• JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 201000009890 sinusitis Diseases 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• YVOFSHPIJOYKSH-NLYBMVFSSA-M sodium rifomycin sv Chemical compound [Na+].OC1=C(C(O)=C2C)C3=C([O-])C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O YVOFSHPIJOYKSH-NLYBMVFSSA-M 0.000 description 1
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 239000001587 sorbitan monostearate Substances 0.000 description 1
• 235000011076 sorbitan monostearate Nutrition 0.000 description 1
• 229940035048 sorbitan monostearate Drugs 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000011550 stock solution Substances 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 229940115920 streptococcus dysgalactiae Drugs 0.000 description 1
• 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
• 229940041030 streptogramins Drugs 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 230000001629 suppression Effects 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 125000001583 thiepanyl group Chemical group 0.000 description 1
• 125000002053 thietanyl group Chemical group 0.000 description 1
• 108020002982 thioesterase Proteins 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 238000003354 tissue distribution assay Methods 0.000 description 1
• YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
• 206010044008 tonsillitis Diseases 0.000 description 1
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 239000011573 trace mineral Substances 0.000 description 1
• 235000013619 trace mineral Nutrition 0.000 description 1
• 230000002103 transcriptional effect Effects 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 108091005703 transmembrane proteins Proteins 0.000 description 1
• 102000035160 transmembrane proteins Human genes 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 231100000397 ulcer Toxicity 0.000 description 1
• 210000003708 urethra Anatomy 0.000 description 1
• MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
• 229960003165 vancomycin Drugs 0.000 description 1
• MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
• 235000013311 vegetables Nutrition 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 239000003871 white petrolatum Substances 0.000 description 1
• 238000010626 work up procedure Methods 0.000 description 1
• 150000003751 zinc Chemical class 0.000 description 1
• 150000003952 β-lactams Chemical class 0.000 description 1