BE487577A - - Google Patents
Info
- Publication number
- BE487577A BE487577A BE487577DA BE487577A BE 487577 A BE487577 A BE 487577A BE 487577D A BE487577D A BE 487577DA BE 487577 A BE487577 A BE 487577A
- Authority
- BE
- Belgium
- Prior art keywords
- penicillin
- procaine
- amine
- soluble
- salt
- Prior art date
Links
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 193
- 229940049954 Penicillin Drugs 0.000 claims description 187
- 229960000626 benzylpenicillin Drugs 0.000 claims description 187
- 239000011780 sodium chloride Substances 0.000 claims description 66
- 150000003839 salts Chemical class 0.000 claims description 59
- 239000000243 solution Substances 0.000 claims description 54
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 52
- 230000003115 biocidal Effects 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 37
- 238000002360 preparation method Methods 0.000 claims description 37
- 150000001412 amines Chemical class 0.000 claims description 33
- UCSJYZPVAKXKNQ-HZYVHMACSA-N 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 32
- 235000010323 ascorbic acid Nutrition 0.000 claims description 31
- 239000011668 ascorbic acid Substances 0.000 claims description 30
- -1 amine salt Chemical class 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 29
- 229910052751 metal Inorganic materials 0.000 claims description 28
- 239000002184 metal Substances 0.000 claims description 28
- 239000004202 carbamide Substances 0.000 claims description 26
- 229960005070 ascorbic acid Drugs 0.000 claims description 22
- NLJVXZFCYKWXLH-DXTIXLATSA-N 3-[(3R,6S,9S,12S,15S,17S,20S,22R,25S,28S)-20-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-3,22,25-tribenzyl-15-[(4-hydroxyphenyl)methyl]-6-(2-methylpropyl)-2,5,8,11,14,18,21,24,27-nonaoxo-12-propan-2-yl-1,4,7,10,13,16,19,23,26-nonazabicyclo[26.3.0]hentriacontan Chemical compound C([C@H]1C(=O)N[C@H](C(=O)N[C@@H](CCCN)C(=O)N[C@H](C(N[C@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)N1)=O)CC(C)C)C(C)C)C1=CC=C(O)C=C1 NLJVXZFCYKWXLH-DXTIXLATSA-N 0.000 claims description 20
- 108010021006 Tyrothricin Proteins 0.000 claims description 20
- 229960003281 tyrothricin Drugs 0.000 claims description 20
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Vitamin C Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- MFDFERRIHVXMIY-UHFFFAOYSA-N Procaine Chemical group CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims description 18
- 229960004919 procaine Drugs 0.000 claims description 18
- 229940072107 Ascorbate Drugs 0.000 claims description 16
- TYQCGQRIZGCHNB-JLAZNSOCSA-N L-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 claims description 16
- 229960005322 Streptomycin Drugs 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- WHRVRSCEWKLAHX-LQDWTQKMSA-N benzylpenicillin procaine Chemical compound [H+].CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 WHRVRSCEWKLAHX-LQDWTQKMSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 239000003242 anti bacterial agent Substances 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 12
- 229910052708 sodium Inorganic materials 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 11
- 229940064005 Antibiotic throat preparations Drugs 0.000 claims description 10
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 claims description 10
- 229940042052 Antibiotics for systemic use Drugs 0.000 claims description 10
- 229940042786 Antitubercular Antibiotics Drugs 0.000 claims description 10
- 229940093922 Gynecological Antibiotics Drugs 0.000 claims description 10
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 claims description 10
- 150000001413 amino acids Chemical class 0.000 claims description 10
- 230000000844 anti-bacterial Effects 0.000 claims description 10
- 229940079866 intestinal antibiotics Drugs 0.000 claims description 10
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- MYWUZJCMWCOHBA-UHFFFAOYSA-N N-methyl-1-phenylpropan-2-amine Chemical group CNC(C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-UHFFFAOYSA-N 0.000 claims description 9
- 229960001295 Tocopherol Drugs 0.000 claims description 9
- 235000010384 tocopherol Nutrition 0.000 claims description 9
- 239000011732 tocopherol Substances 0.000 claims description 9
- 229930003799 tocopherols Natural products 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000003531 protein hydrolysate Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 230000001975 sympathomimetic Effects 0.000 claims description 7
- VKYKSIONXSXAKP-UHFFFAOYSA-N Hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 6
- 229960004011 Methenamine Drugs 0.000 claims description 6
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000150 Sympathomimetic Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 6
- 150000002736 metal compounds Chemical class 0.000 claims description 6
- 229960001663 sulfanilamide Drugs 0.000 claims description 6
- 108010009736 Protein Hydrolysates Proteins 0.000 claims description 5
- JNMRHUJNCSQMMB-UHFFFAOYSA-N Sulfathiazole Chemical group C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 5
- 229960002685 biotin Drugs 0.000 claims description 5
- 235000020958 biotin Nutrition 0.000 claims description 5
- 239000011616 biotin Substances 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 229960001544 sulfathiazole Drugs 0.000 claims description 5
- 230000036826 Excretion Effects 0.000 claims description 4
- 229930013930 alkaloids Natural products 0.000 claims description 4
- 230000029142 excretion Effects 0.000 claims description 4
- 230000002829 reduced Effects 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-Aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N Glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 2
- 229960003180 Glutathione Drugs 0.000 claims description 2
- 108010024636 Glutathione Proteins 0.000 claims description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 229960004838 Phosphoric acid Drugs 0.000 claims 2
- 230000002035 prolonged Effects 0.000 claims 2
- 150000000996 L-ascorbic acids Chemical class 0.000 claims 1
- 229940064707 Sympathomimetics Drugs 0.000 claims 1
- 150000003797 alkaloid derivatives Chemical class 0.000 claims 1
- 229960004050 aminobenzoic acid Drugs 0.000 claims 1
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000006228 supernatant Substances 0.000 claims 1
- ZJHHPAUQMCHPRB-UHFFFAOYSA-N urea urea Chemical compound NC(N)=O.NC(N)=O ZJHHPAUQMCHPRB-UHFFFAOYSA-N 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 10
- 229910052791 calcium Inorganic materials 0.000 description 10
- 239000011575 calcium Substances 0.000 description 10
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 230000001225 therapeutic Effects 0.000 description 10
- 235000001014 amino acid Nutrition 0.000 description 9
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 9
- 230000000087 stabilizing Effects 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 7
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 7
- 229960005055 SODIUM ASCORBATE Drugs 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 239000002674 ointment Substances 0.000 description 7
- 235000010378 sodium ascorbate Nutrition 0.000 description 7
- 210000004369 Blood Anatomy 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 230000001745 anti-biotin Effects 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000003000 nontoxic Effects 0.000 description 6
- 231100000252 nontoxic Toxicity 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000006046 creatine Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 4
- 229960003624 Creatine Drugs 0.000 description 4
- KWGRBVOPPLSCSI-WPRPVWTQSA-N Ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 4
- 239000004472 Lysine Substances 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine zwitterion Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 230000002633 protecting Effects 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 210000001519 tissues Anatomy 0.000 description 4
- 230000002588 toxic Effects 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 150000003672 ureas Chemical class 0.000 description 4
- PLKYJWLKIDFVHM-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;urea Chemical compound NC(N)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O PLKYJWLKIDFVHM-UHFFFAOYSA-N 0.000 description 3
- 229940025084 Amphetamine Drugs 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 3
- 210000004051 Gastric Juice Anatomy 0.000 description 3
- 210000002850 Nasal Mucosa Anatomy 0.000 description 3
- 210000002700 Urine Anatomy 0.000 description 3
- 230000002378 acidificating Effects 0.000 description 3
- 229960002734 amfetamine Drugs 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 229940079593 drugs Drugs 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000010255 intramuscular injection Methods 0.000 description 3
- 239000007927 intramuscular injection Substances 0.000 description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000001603 reducing Effects 0.000 description 3
- 239000008159 sesame oil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 229930006677 A03BA01 - Atropine Natural products 0.000 description 2
- UDMBCSSLTHHNCD-KQYNXXCUSA-N Adenosine monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N Atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 Atropine Drugs 0.000 description 2
- 229960003067 Cystine Drugs 0.000 description 2
- 229940093915 Gynecological Organic acids Drugs 0.000 description 2
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine zwitterion Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 2
- 210000000214 Mouth Anatomy 0.000 description 2
- 210000001331 Nose Anatomy 0.000 description 2
- BRBKOPJOKNSWSG-UHFFFAOYSA-N Sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 description 2
- QPPBRPIAZZHUNT-UHFFFAOYSA-N Sulfamerazine Chemical compound CC1=CC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 QPPBRPIAZZHUNT-UHFFFAOYSA-N 0.000 description 2
- 229960002597 Sulfamerazine Drugs 0.000 description 2
- HMNOVBZVCHMSQG-UHFFFAOYSA-N [Na].NCCO Chemical compound [Na].NCCO HMNOVBZVCHMSQG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000003385 bacteriostatic Effects 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001615 biotins Chemical class 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- ORMNPSYMZOGSSV-UHFFFAOYSA-N dinitrooxymercury Chemical compound [Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ORMNPSYMZOGSSV-UHFFFAOYSA-N 0.000 description 2
- 201000009910 diseases by infectious agent Diseases 0.000 description 2
- RDJCIKZLXHKBPH-SEPHDYHBSA-L disodium;5-[2-(4-oxocyclohexa-2,5-dien-1-ylidene)hydrazinyl]-2-[(E)-2-[4-[2-(4-oxocyclohexa-2,5-dien-1-ylidene)hydrazinyl]-2-sulfonatophenyl]ethenyl]benzenesulfonate Chemical compound [Na+].[Na+].C=1C=C(\C=C\C=2C(=CC(NN=C3C=CC(=O)C=C3)=CC=2)S([O-])(=O)=O)C(S(=O)(=O)[O-])=CC=1NN=C1C=CC(=O)C=C1 RDJCIKZLXHKBPH-SEPHDYHBSA-L 0.000 description 2
- 230000002708 enhancing Effects 0.000 description 2
- 229960002179 ephedrine Drugs 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 230000002349 favourable Effects 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000002496 gastric Effects 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000000879 imine group Chemical group 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- BJHIKXHVCXFQLS-PYWDMBMJSA-N keto-D-sorbose Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)C(=O)CO BJHIKXHVCXFQLS-PYWDMBMJSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 201000009890 sinusitis Diseases 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 2
- 229960004306 sulfadiazine Drugs 0.000 description 2
- 229960004257 sulfaguanidine Drugs 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
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- CIWBSHSKHKDKBQ-MVHIGOERSA-N D-ascorbic acid Chemical compound OC[C@@H](O)[C@@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-MVHIGOERSA-N 0.000 description 1
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- UCTWMZQNUQWSLP-VIFPVBQESA-N Epinephrine Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
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- 206010028735 Nasal congestion Diseases 0.000 description 1
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- 206010035664 Pneumonia Diseases 0.000 description 1
- 229960001309 Procaine hydrochloride Drugs 0.000 description 1
- HCBIBCJNVBAKAB-UHFFFAOYSA-N Procaine hydrochloride Chemical compound Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 HCBIBCJNVBAKAB-UHFFFAOYSA-N 0.000 description 1
- 210000004915 Pus Anatomy 0.000 description 1
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- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- GECHUMIMRBOMGK-UHFFFAOYSA-N Sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 1
- 206010044008 Tonsillitis Diseases 0.000 description 1
- 206010046577 Urinary tract infection Diseases 0.000 description 1
- 206010046736 Urticarias Diseases 0.000 description 1
- 240000006745 Valeriana officinalis Species 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 206010048629 Wound secretion Diseases 0.000 description 1
- MWAZVPWTTWPXJF-UHFFFAOYSA-N acetic acid;urea Chemical compound CC(O)=O.NC(N)=O MWAZVPWTTWPXJF-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating Effects 0.000 description 1
- 230000001154 acute Effects 0.000 description 1
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- 235000004279 alanine Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
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- 229940087168 alpha Tocopherol Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002921 anti-spasmodic Effects 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- NSGOVOMOUNRVAC-UHFFFAOYSA-N benzoic acid;urea Chemical compound NC(N)=O.OC(=O)C1=CC=CC=C1 NSGOVOMOUNRVAC-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 230000003139 buffering Effects 0.000 description 1
- 235000010376 calcium ascorbate Nutrition 0.000 description 1
- 239000011692 calcium ascorbate Substances 0.000 description 1
- BLORRZQTHNGFTI-ZZMNMWMASA-L calcium-L-ascorbate Chemical compound [Ca+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BLORRZQTHNGFTI-ZZMNMWMASA-L 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 230000000295 complement Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000003111 delayed Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000003203 everyday Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000002949 hemolytic Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 230000002045 lasting Effects 0.000 description 1
- 201000009906 meningitis Diseases 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000035786 metabolism Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000008729 phenylalanine Nutrition 0.000 description 1
- LUBJCRLGQSPQNN-UHFFFAOYSA-N phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000002980 postoperative Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001698 pyrogenic Effects 0.000 description 1
- 230000000717 retained Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 229960002211 sulfapyridine Drugs 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002195 synergetic Effects 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 238000007483 tonsillectomy Methods 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000000083 urinary anti-infective agent Substances 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- LTVDFSLWFKLJDQ-UHFFFAOYSA-N α-Tocopherolquinone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-UHFFFAOYSA-N 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE487577A true BE487577A (de) |
Family
ID=132981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE487577D BE487577A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE487577A (de) |
-
0
- BE BE487577D patent/BE487577A/fr unknown
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