HUE028667T2 - Parenteral administration of azole pharmaceutical compositions for use in treating diseases susceptible to azole compounds and methods for their preparation. - Google Patents
Parenteral administration of azole pharmaceutical compositions for use in treating diseases susceptible to azole compounds and methods for their preparation. Download PDFInfo
- Publication number
- HUE028667T2 HUE028667T2 HUE11849408A HUE11849408A HUE028667T2 HU E028667 T2 HUE028667 T2 HU E028667T2 HU E11849408 A HUE11849408 A HU E11849408A HU E11849408 A HUE11849408 A HU E11849408A HU E028667 T2 HUE028667 T2 HU E028667T2
- Authority
- HU
- Hungary
- Prior art keywords
- solvent
- itza
- peg
- azole
- drug
- Prior art date
Links
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title claims description 121
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 16
- 201000010099 disease Diseases 0.000 title claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 238000011282 treatment Methods 0.000 title description 30
- 238000000034 method Methods 0.000 title description 26
- 150000003851 azoles Chemical class 0.000 title description 25
- 238000007911 parenteral administration Methods 0.000 title description 14
- 239000002904 solvent Substances 0.000 claims description 198
- 239000000203 mixture Substances 0.000 claims description 185
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 165
- 238000009472 formulation Methods 0.000 claims description 100
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- 239000003795 chemical substances by application Substances 0.000 claims description 36
- 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 claims description 35
- 239000008121 dextrose Substances 0.000 claims description 34
- 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 claims description 33
- 239000003978 infusion fluid Substances 0.000 claims description 33
- 238000010790 dilution Methods 0.000 claims description 15
- 239000012895 dilution Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000003852 triazoles Chemical class 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 239000008177 pharmaceutical agent Substances 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 241000193830 Bacillus <bacterium> Species 0.000 claims 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 1
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims 1
- 229940069428 antacid Drugs 0.000 claims 1
- 239000003159 antacid agent Substances 0.000 claims 1
- 230000001458 anti-acid effect Effects 0.000 claims 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 claims 1
- 230000000366 juvenile effect Effects 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 210000005070 sphincter Anatomy 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 141
- 239000003814 drug Substances 0.000 description 104
- 229940079593 drug Drugs 0.000 description 101
- RAGOYPUPXAKGKH-XAKZXMRKSA-N posaconazole Chemical compound O=C1N([C@H]([C@H](C)O)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@H]3C[C@@](CN4N=CN=C4)(OC3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 RAGOYPUPXAKGKH-XAKZXMRKSA-N 0.000 description 91
- 229960001589 posaconazole Drugs 0.000 description 91
- 239000003981 vehicle Substances 0.000 description 78
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 51
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 50
- 235000019445 benzyl alcohol Nutrition 0.000 description 45
- 210000002381 plasma Anatomy 0.000 description 44
- 239000002131 composite material Substances 0.000 description 43
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 42
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 41
- 208000015181 infectious disease Diseases 0.000 description 40
- 239000003085 diluting agent Substances 0.000 description 37
- 238000004128 high performance liquid chromatography Methods 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 229960004130 itraconazole Drugs 0.000 description 32
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 description 30
- 241000282414 Homo sapiens Species 0.000 description 28
- 241001465754 Metazoa Species 0.000 description 27
- 230000000843 anti-fungal effect Effects 0.000 description 24
- 229940121375 antifungal agent Drugs 0.000 description 24
- 208000031888 Mycoses Diseases 0.000 description 21
- 230000009885 systemic effect Effects 0.000 description 21
- 238000002474 experimental method Methods 0.000 description 20
- 230000000694 effects Effects 0.000 description 19
- 239000013543 active substance Substances 0.000 description 18
- 210000004369 blood Anatomy 0.000 description 18
- 239000008280 blood Substances 0.000 description 18
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 241000699670 Mus sp. Species 0.000 description 17
- 239000000523 sample Substances 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 16
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 16
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 16
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 15
- -1 Emulgen 913 Chemical compound 0.000 description 15
- 206010017533 Fungal infection Diseases 0.000 description 15
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 14
- 238000001802 infusion Methods 0.000 description 14
- 230000036470 plasma concentration Effects 0.000 description 14
- 230000031891 intestinal absorption Effects 0.000 description 13
- 239000002736 nonionic surfactant Substances 0.000 description 13
- 238000000338 in vitro Methods 0.000 description 12
- 238000010268 HPLC based assay Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 230000037396 body weight Effects 0.000 description 11
- 238000000605 extraction Methods 0.000 description 11
- 241000282412 Homo Species 0.000 description 10
- 241000124008 Mammalia Species 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 9
- 230000002924 anti-infective effect Effects 0.000 description 9
- 230000008901 benefit Effects 0.000 description 9
- 230000002949 hemolytic effect Effects 0.000 description 9
- 239000002960 lipid emulsion Substances 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- 239000003643 water by type Substances 0.000 description 9
- 206010061598 Immunodeficiency Diseases 0.000 description 8
- 239000003429 antifungal agent Substances 0.000 description 8
- 230000002198 cosolvency Effects 0.000 description 8
- 230000008030 elimination Effects 0.000 description 8
- 238000003379 elimination reaction Methods 0.000 description 8
- 229960004884 fluconazole Drugs 0.000 description 8
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 230000000968 intestinal effect Effects 0.000 description 8
- 150000002632 lipids Chemical class 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- 231100000252 nontoxic Toxicity 0.000 description 8
- 230000003000 nontoxic effect Effects 0.000 description 8
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 8
- 238000005063 solubilization Methods 0.000 description 8
- 230000007928 solubilization Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000002560 therapeutic procedure Methods 0.000 description 8
- 102000004506 Blood Proteins Human genes 0.000 description 7
- 108010017384 Blood Proteins Proteins 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 238000001647 drug administration Methods 0.000 description 7
- 230000002440 hepatic effect Effects 0.000 description 7
- 230000002035 prolonged effect Effects 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 7
- 229960004740 voriconazole Drugs 0.000 description 7
- 208000037026 Invasive Fungal Infections Diseases 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 238000002512 chemotherapy Methods 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000002538 fungal effect Effects 0.000 description 6
- 230000001408 fungistatic effect Effects 0.000 description 6
- 238000001990 intravenous administration Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 230000010412 perfusion Effects 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 6
- 229920000053 polysorbate 80 Polymers 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 5
- 241000228212 Aspergillus Species 0.000 description 5
- 241001225321 Aspergillus fumigatus Species 0.000 description 5
- 206010018910 Haemolysis Diseases 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 229940091771 aspergillus fumigatus Drugs 0.000 description 5
- 239000006184 cosolvent Substances 0.000 description 5
- 239000013583 drug formulation Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 210000003743 erythrocyte Anatomy 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 230000008588 hemolysis Effects 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 229940126701 oral medication Drugs 0.000 description 5
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 5
- 229940068968 polysorbate 80 Drugs 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- ZCJYUTQZBAIHBS-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-{[4-(phenylsulfanyl)benzyl]oxy}ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C=CC(SC=2C=CC=CC=2)=CC=1)CN1C=NC=C1 ZCJYUTQZBAIHBS-UHFFFAOYSA-N 0.000 description 4
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 description 4
- QXHHHPZILQDDPS-UHFFFAOYSA-N 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound S1C=CC(COC(CN2C=NC=C2)C=2C(=CC(Cl)=CC=2)Cl)=C1Cl QXHHHPZILQDDPS-UHFFFAOYSA-N 0.000 description 4
- JLGKQTAYUIMGRK-UHFFFAOYSA-N 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C2=CC=CC(Cl)=C2SC=1)CN1C=NC=C1 JLGKQTAYUIMGRK-UHFFFAOYSA-N 0.000 description 4
- 201000002909 Aspergillosis Diseases 0.000 description 4
- 208000036641 Aspergillus infections Diseases 0.000 description 4
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 4
- 206010007134 Candida infections Diseases 0.000 description 4
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 4
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 4
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 4
- TYBHXIFFPVFXQW-UHFFFAOYSA-N abafungin Chemical compound CC1=CC(C)=CC=C1OC1=CC=CC=C1C1=CSC(NC=2NCCCN=2)=N1 TYBHXIFFPVFXQW-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- SWLMUYACZKCSHZ-UHFFFAOYSA-N butoconazole Chemical compound C1=CC(Cl)=CC=C1CCC(SC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 SWLMUYACZKCSHZ-UHFFFAOYSA-N 0.000 description 4
- 201000003984 candidiasis Diseases 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 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 4
- 230000036541 health Effects 0.000 description 4
- 239000012678 infectious agent Substances 0.000 description 4
- 238000007913 intrathecal administration Methods 0.000 description 4
- DDFOUSQFMYRUQK-RCDICMHDSA-N isavuconazole Chemical compound C=1SC([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC=C(F)C=2)F)=NC=1C1=CC=C(C#N)C=C1 DDFOUSQFMYRUQK-RCDICMHDSA-N 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 238000010172 mouse model Methods 0.000 description 4
- 201000007524 mucormycosis Diseases 0.000 description 4
- JMFOSJNGKJCTMJ-ZHZULCJRSA-N omoconazole Chemical compound C1=CN=CN1C(/C)=C(C=1C(=CC(Cl)=CC=1)Cl)\OCCOC1=CC=C(Cl)C=C1 JMFOSJNGKJCTMJ-ZHZULCJRSA-N 0.000 description 4
- QRJJEGAJXVEBNE-MOHJPFBDSA-N oxiconazole Chemical compound ClC1=CC(Cl)=CC=C1CO\N=C(C=1C(=CC(Cl)=CC=1)Cl)\CN1C=NC=C1 QRJJEGAJXVEBNE-MOHJPFBDSA-N 0.000 description 4
- 235000016236 parenteral nutrition Nutrition 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- 239000008389 polyethoxylated castor oil Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- OPAHEYNNJWPQPX-RCDICMHDSA-N ravuconazole Chemical compound C=1SC([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=1C1=CC=C(C#N)C=C1 OPAHEYNNJWPQPX-RCDICMHDSA-N 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 4
- BLSQLHNBWJLIBQ-OZXSUGGESA-N (2R,4S)-terconazole Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2N=CN=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 BLSQLHNBWJLIBQ-OZXSUGGESA-N 0.000 description 3
- MPIPASJGOJYODL-SFHVURJKSA-N (R)-isoconazole Chemical compound ClC1=CC(Cl)=CC=C1[C@@H](OCC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 MPIPASJGOJYODL-SFHVURJKSA-N 0.000 description 3
- AFNXATANNDIXLG-SFHVURJKSA-N 1-[(2r)-2-[(4-chlorophenyl)methylsulfanyl]-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound C1=CC(Cl)=CC=C1CS[C@H](C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 AFNXATANNDIXLG-SFHVURJKSA-N 0.000 description 3
- LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 description 3
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 3
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=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-KKGHZKTASA-N 0.000 description 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 208000009329 Graft vs Host Disease Diseases 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
- 229920002593 Polyethylene Glycol 800 Polymers 0.000 description 3
- 229950006373 abafungin Drugs 0.000 description 3
- 230000000735 allogeneic effect Effects 0.000 description 3
- 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 3
- 229960003942 amphotericin b Drugs 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 229960002206 bifonazole Drugs 0.000 description 3
- 229960005074 butoconazole Drugs 0.000 description 3
- 238000012754 cardiac puncture Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000002144 chemical decomposition reaction Methods 0.000 description 3
- 229960004022 clotrimazole Drugs 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 238000012377 drug delivery Methods 0.000 description 3
- 229960001274 fenticonazole Drugs 0.000 description 3
- 208000024908 graft versus host disease Diseases 0.000 description 3
- 238000011134 hematopoietic stem cell transplantation Methods 0.000 description 3
- 229940028435 intralipid Drugs 0.000 description 3
- 201000009085 invasive aspergillosis Diseases 0.000 description 3
- 229960000788 isavuconazole Drugs 0.000 description 3
- 229960004849 isoconazole Drugs 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 230000003211 malignant effect Effects 0.000 description 3
- 229960003439 mebendazole Drugs 0.000 description 3
- 238000002483 medication Methods 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 229960002509 miconazole Drugs 0.000 description 3
- 229960004031 omoconazole Drugs 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229960003483 oxiconazole Drugs 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 229950004154 ravuconazole Drugs 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229960005429 sertaconazole Drugs 0.000 description 3
- 229960002607 sulconazole Drugs 0.000 description 3
- 229960000580 terconazole Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 229960004214 tioconazole Drugs 0.000 description 3
- 210000003462 vein Anatomy 0.000 description 3
- 239000011800 void material Substances 0.000 description 3
- YJGVMLPVUAXIQN-LGWHJFRWSA-N (5s,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one Chemical class COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-LGWHJFRWSA-N 0.000 description 2
- 108010006654 Bleomycin Proteins 0.000 description 2
- 108010078777 Colistin Proteins 0.000 description 2
- 208000028399 Critical Illness Diseases 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- 108020004414 DNA Proteins 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- 108010049047 Echinocandins Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 206010064147 Gastrointestinal inflammation Diseases 0.000 description 2
- 102000001554 Hemoglobins Human genes 0.000 description 2
- 108010054147 Hemoglobins Proteins 0.000 description 2
- 241000228402 Histoplasma Species 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 108010093965 Polymyxin B Proteins 0.000 description 2
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 2
- 206010036590 Premature baby Diseases 0.000 description 2
- 102220569751 Pyridoxal-dependent decarboxylase domain-containing protein 1_M38A_mutation Human genes 0.000 description 2
- 229940123237 Taxane Drugs 0.000 description 2
- 206010066901 Treatment failure Diseases 0.000 description 2
- 206010061418 Zygomycosis Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 229940045799 anthracyclines and related substance Drugs 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 2
- 239000000164 antipsychotic agent Substances 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229960001561 bleomycin Drugs 0.000 description 2
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- 229960003346 colistin Drugs 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 231100000599 cytotoxic agent Toxicity 0.000 description 2
- 239000002254 cytotoxic agent Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000010339 dilation Effects 0.000 description 2
- 229960003913 econazole Drugs 0.000 description 2
- 239000002786 epipodophyllotoxin derivative Substances 0.000 description 2
- 238000010579 first pass effect Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 208000018925 gastrointestinal mucositis Diseases 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 230000002458 infectious effect Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000003871 intestinal function Effects 0.000 description 2
- VHVPQPYKVGDNFY-ZPGVKDDISA-N itraconazole Chemical compound O=C1N(C(C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-ZPGVKDDISA-N 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 description 2
- JORAUNFTUVJTNG-BSTBCYLQSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Chemical compound CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O JORAUNFTUVJTNG-BSTBCYLQSA-N 0.000 description 2
- 229960003255 natamycin Drugs 0.000 description 2
- 239000004311 natamycin Substances 0.000 description 2
- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin 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@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 description 2
- 235000010298 natamycin Nutrition 0.000 description 2
- 230000001613 neoplastic effect Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 235000021542 oral nutrition Nutrition 0.000 description 2
- 229940100692 oral suspension Drugs 0.000 description 2
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000001050 pharmacotherapy Methods 0.000 description 2
- 150000003058 platinum compounds Chemical class 0.000 description 2
- 150000004291 polyenes Chemical class 0.000 description 2
- 229920000024 polymyxin B Polymers 0.000 description 2
- XDJYMJULXQKGMM-UHFFFAOYSA-N polymyxin E1 Natural products CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O XDJYMJULXQKGMM-UHFFFAOYSA-N 0.000 description 2
- KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 description 2
- 229960005266 polymyxin b Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000006920 protein precipitation Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001959 radiotherapy Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000011476 stem cell transplantation Methods 0.000 description 2
- 238000007910 systemic administration Methods 0.000 description 2
- 230000001839 systemic circulation Effects 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
- BLSQLHNBWJLIBQ-ZEQKJWHPSA-N (2S,4R)-terconazole Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1OC[C@H]1O[C@](CN2N=CN=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 BLSQLHNBWJLIBQ-ZEQKJWHPSA-N 0.000 description 1
- MPIPASJGOJYODL-UHFFFAOYSA-N 1-{2-[(2,6-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 MPIPASJGOJYODL-UHFFFAOYSA-N 0.000 description 1
- AFNXATANNDIXLG-UHFFFAOYSA-N 1-{2-[(4-chlorobenzyl)sulfanyl]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole Chemical compound C1=CC(Cl)=CC=C1CSC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 AFNXATANNDIXLG-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- NLMKTBGFQGKQEV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hexadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO NLMKTBGFQGKQEV-UHFFFAOYSA-N 0.000 description 1
- JKXYOQDLERSFPT-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-octadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO JKXYOQDLERSFPT-UHFFFAOYSA-N 0.000 description 1
- IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 208000002310 Achlorhydria Diseases 0.000 description 1
- 206010000830 Acute leukaemia Diseases 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 244000251953 Agaricus brunnescens Species 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 206010001605 Alcohol poisoning Diseases 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 206010005098 Blastomycosis Diseases 0.000 description 1
- 206010006473 Bronchopulmonary aspergillosis Diseases 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 206010013710 Drug interaction Diseases 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- 208000003241 Fat Embolism Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010016948 Food interaction Diseases 0.000 description 1
- 208000004770 Fusariosis Diseases 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 description 1
- 201000002563 Histoplasmosis Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
- 208000021251 Methanol poisoning Diseases 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241000235388 Mucorales Species 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 208000010195 Onychomycosis Diseases 0.000 description 1
- 206010050346 Oropharyngeal candidiasis Diseases 0.000 description 1
- 208000001300 Perinatal Death Diseases 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 229920001219 Polysorbate 40 Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 229920002642 Polysorbate 65 Polymers 0.000 description 1
- 208000004430 Pulmonary Aspergillosis Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000005074 Retroviridae Infections Diseases 0.000 description 1
- 241000235402 Rhizomucor Species 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010042938 Systemic candida Diseases 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 206010046914 Vaginal infection Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 201000007096 Vulvovaginal Candidiasis Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- 238000011483 antifungal activity assay Methods 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 150000007980 azole derivatives Chemical class 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 210000003995 blood forming stem cell Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
- 229960001704 carbimazole Drugs 0.000 description 1
- CFOYWRHIYXMDOT-UHFFFAOYSA-N carbimazole Chemical compound CCOC(=O)N1C=CN(C)C1=S CFOYWRHIYXMDOT-UHFFFAOYSA-N 0.000 description 1
- 238000011208 chromatographic data Methods 0.000 description 1
- 229940121657 clinical drug Drugs 0.000 description 1
- 238000011281 clinical therapy Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000011254 conventional chemotherapy Methods 0.000 description 1
- 230000010485 coping Effects 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 230000008406 drug-drug interaction Effects 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 210000004905 finger nail Anatomy 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 230000009246 food effect Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000002695 general anesthesia Methods 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 210000003958 hematopoietic stem cell Anatomy 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 210000004276 hyalin Anatomy 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 208000036732 invasive candidiasis Diseases 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- 229960004125 ketoconazole Drugs 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- PGXWDLGWMQIXDT-UHFFFAOYSA-N methylsulfinylmethane;hydrate Chemical compound O.CS(C)=O PGXWDLGWMQIXDT-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003228 microsomal effect Effects 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000002071 myeloproliferative effect Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000002560 nonimmunologic effect Effects 0.000 description 1
- 229940087419 nonoxynol-9 Drugs 0.000 description 1
- 229920004918 nonoxynol-9 Polymers 0.000 description 1
- 229940099075 noxafil Drugs 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229940101027 polysorbate 40 Drugs 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 229940099511 polysorbate 65 Drugs 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000009101 premedication Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- 229960004134 propofol Drugs 0.000 description 1
- 235000004252 protein component Nutrition 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 210000005000 reproductive tract Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000837 restrainer Substances 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 208000003265 stomatitis Diseases 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000008337 systemic blood flow Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 201000005882 tinea unguium Diseases 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- 210000004906 toe nail Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000155 toxicity by organ Toxicity 0.000 description 1
- 230000007675 toxicity by organ Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/417—Imidazole-alkylamines, e.g. histamine, phentolamine
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Oncology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42393710P | 2010-12-16 | 2010-12-16 | |
| US201161509154P | 2011-07-19 | 2011-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE028667T2 true HUE028667T2 (en) | 2016-12-28 |
Family
ID=46245384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE11849408A HUE028667T2 (en) | 2010-12-16 | 2011-12-16 | Parenteral administration of azole pharmaceutical compositions for use in treating diseases susceptible to azole compounds and methods for their preparation. |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US10307418B2 (enExample) |
| EP (1) | EP2651450B1 (enExample) |
| JP (2) | JP6086539B2 (enExample) |
| CN (1) | CN103402543B (enExample) |
| AU (1) | AU2011343576B2 (enExample) |
| BR (1) | BR112013015085A8 (enExample) |
| CA (1) | CA2821823C (enExample) |
| DK (1) | DK2651450T3 (enExample) |
| ES (1) | ES2565353T3 (enExample) |
| HU (1) | HUE028667T2 (enExample) |
| IL (1) | IL226977A (enExample) |
| MX (1) | MX337364B (enExample) |
| NZ (1) | NZ613167A (enExample) |
| RU (2) | RU2618456C2 (enExample) |
| WO (1) | WO2012083138A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ613167A (en) * | 2010-12-16 | 2015-09-25 | Univ Texas | Azole pharmaceutical formulations for parenteral administration and methods for preparing and using the same as treatment of diseases sensitive to azole compounds |
| ES2822350T3 (es) * | 2011-04-28 | 2021-04-30 | Platform Brightworks Two Ltd | Formulaciones parenterales mejoradas de agentes farmacéuticos lipófilos y procedimientos de preparación y uso de las mismas |
| SG11201504976UA (en) * | 2012-12-28 | 2015-07-30 | Suntory Holdings Ltd | Non-alcohol, beer-taste beverage having shimari in taste |
| CN105394045B (zh) * | 2014-09-04 | 2020-02-14 | 中国科学院上海巴斯德研究所 | 一种肠道病毒的小分子化合物抑制剂及其应用 |
| CN105943500B (zh) * | 2016-07-08 | 2019-01-04 | 河南省立眼科医院 | 一种含有艾沙康唑的眼用纳米胶束抗真菌溶液 |
| TWI834808B (zh) | 2019-02-19 | 2024-03-11 | 西班牙商薩爾瓦特實驗室有限公司 | 以單劑包裝的克氯黴唑液體組成物 |
| CN111665301A (zh) * | 2020-05-29 | 2020-09-15 | 南京品生医疗科技有限公司 | 超高效液相色谱串联质谱技术检测血清中抗真菌药物的试剂盒 |
| CN116507319A (zh) * | 2020-11-16 | 2023-07-28 | W.L.戈尔及同仁股份有限公司 | 不含浊点的制剂、方法和预填充多剂量注射装置 |
| CN113671086B (zh) * | 2021-08-31 | 2023-06-16 | 重庆华邦制药有限公司 | 分离、测定泊沙康唑z2及其杂质的方法 |
| CN114660200A (zh) * | 2022-03-29 | 2022-06-24 | 中国人民解放军总医院 | 一种高效液相色谱串联质谱技术同时测定血浆中4种三唑类抗真菌药物的方法 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4912124A (en) * | 1984-02-23 | 1990-03-27 | Ortho Pharmaceutical Corporation | Antifungal dermatological solution |
| DE3702105A1 (de) | 1987-01-24 | 1988-08-04 | Bayer Ag | Parenterale loesung |
| JPH01242525A (ja) | 1988-03-25 | 1989-09-27 | Nippon Nohyaku Co Ltd | 抗真菌外用剤 |
| PH30929A (en) * | 1992-09-03 | 1997-12-23 | Janssen Pharmaceutica Nv | Beads having a core coated with an antifungal and a polymer. |
| PH31594A (en) * | 1993-09-30 | 1998-11-03 | Janssen Pharmaceutica Nv | Oral formulations on an antifungal. |
| KR0159730B1 (ko) * | 1996-01-15 | 1998-12-01 | 손경식 | 케토코나졸 수성 제제 |
| US7179475B1 (en) * | 1998-12-04 | 2007-02-20 | Johnson & Johnson Consumer Companies, Inc. | Anhydrous topical skin preparations |
| US6362172B2 (en) * | 2000-01-20 | 2002-03-26 | Bristol-Myers Squibb Company | Water soluble prodrugs of azole compounds |
| GB2365770B (en) | 2000-08-18 | 2002-07-31 | Diomed Dev Ltd | Antifungal ketoconazole composition for topical use |
| US20050048126A1 (en) * | 2000-12-22 | 2005-03-03 | Barrett Rabinow | Formulation to render an antimicrobial drug potent against organisms normally considered to be resistant to the drug |
| US20030072807A1 (en) * | 2000-12-22 | 2003-04-17 | Wong Joseph Chung-Tak | Solid particulate antifungal compositions for pharmaceutical use |
| JP2002322056A (ja) | 2001-04-27 | 2002-11-08 | Nippon Kayaku Co Ltd | トリアゾール誘導体の溶液製剤 |
| JP4263441B2 (ja) * | 2002-08-07 | 2009-05-13 | 富士重工業株式会社 | ４輪駆動車の制御装置 |
| WO2004014431A1 (en) | 2002-08-12 | 2004-02-19 | Ranbaxy Laboratories Limited | A parenteral dosage form of selective cox-2 inhibitors |
| ZA200409537B (en) | 2003-01-31 | 2006-10-25 | Yamanouchi Pharma Co Ltd | Stable solid medicinal composition for oral administration |
| US20060003654A1 (en) * | 2004-06-30 | 2006-01-05 | Lostocco Michael R | Dispersible alcohol/cleaning wipes via topical or wet-end application of acrylamide or vinylamide/amine polymers |
| WO2006105399A1 (en) | 2005-03-31 | 2006-10-05 | Bristol-Myers Squibb Company | Methods for administering ixabepilone |
| CA2613389A1 (en) | 2005-06-27 | 2007-01-04 | Barrier Therapeutics, Inc. | Micogel topical formulations |
| US20070082870A1 (en) * | 2005-10-11 | 2007-04-12 | Buchanan Charles M | Pharmaceutical formulations of cyclodextrins and antifungal azole compounds |
| AU2007355106A1 (en) * | 2006-11-29 | 2008-12-18 | Foamix Ltd. | Foamable waterless compositions with modulating agents |
| KR20100075475A (ko) | 2007-09-05 | 2010-07-02 | 가부시키가이샤 폴라 파마 | 의약 조성물 |
| US20090253712A1 (en) | 2008-04-03 | 2009-10-08 | Semmelweis Egyetem | Aqueous solvent system for solubilization of azole compounds |
| WO2009139925A1 (en) * | 2008-05-16 | 2009-11-19 | Panacea Pharmaceuticals, Inc. | Methods for the treatment of brain edema |
| MX2011008204A (es) | 2009-02-05 | 2011-12-06 | Targeted Delivery Technologies Ltd | Metodos para reducir la proliferacion y viabilidad de los agentes microbianos. |
| CN102387785B (zh) | 2009-04-09 | 2017-08-25 | 宝丽制药股份有限公司 | 抗真菌药物组合物 |
| US8252821B2 (en) | 2009-04-14 | 2012-08-28 | Bristol-Myers Squibb Company | Bioavailable capsule compositions of amorphous alpha-(N-sulfonamido)acetamide compound |
| NZ613167A (en) * | 2010-12-16 | 2015-09-25 | Univ Texas | Azole pharmaceutical formulations for parenteral administration and methods for preparing and using the same as treatment of diseases sensitive to azole compounds |
| ES2822350T3 (es) * | 2011-04-28 | 2021-04-30 | Platform Brightworks Two Ltd | Formulaciones parenterales mejoradas de agentes farmacéuticos lipófilos y procedimientos de preparación y uso de las mismas |
-
2011
- 2011-12-16 NZ NZ613167A patent/NZ613167A/en not_active IP Right Cessation
- 2011-12-16 EP EP11849408.7A patent/EP2651450B1/en not_active Not-in-force
- 2011-12-16 DK DK11849408.7T patent/DK2651450T3/en active
- 2011-12-16 RU RU2013132703A patent/RU2618456C2/ru not_active IP Right Cessation
- 2011-12-16 US US13/994,152 patent/US10307418B2/en active Active
- 2011-12-16 ES ES11849408.7T patent/ES2565353T3/es active Active
- 2011-12-16 JP JP2013544816A patent/JP6086539B2/ja not_active Expired - Fee Related
- 2011-12-16 CA CA2821823A patent/CA2821823C/en not_active Expired - Fee Related
- 2011-12-16 WO PCT/US2011/065422 patent/WO2012083138A2/en not_active Ceased
- 2011-12-16 CN CN201180067824.5A patent/CN103402543B/zh not_active Expired - Fee Related
- 2011-12-16 HU HUE11849408A patent/HUE028667T2/en unknown
- 2011-12-16 AU AU2011343576A patent/AU2011343576B2/en not_active Ceased
- 2011-12-16 BR BR112013015085A patent/BR112013015085A8/pt active Search and Examination
- 2011-12-16 MX MX2013006816A patent/MX337364B/es active IP Right Grant
- 2011-12-16 RU RU2016149770A patent/RU2734128C2/ru active
-
2013
- 2013-06-16 IL IL226977A patent/IL226977A/en active IP Right Grant
-
2017
- 2017-01-27 JP JP2017013634A patent/JP6529527B2/ja not_active Expired - Fee Related
-
2019
- 2019-04-16 US US16/385,293 patent/US20190240216A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| RU2016149770A3 (enExample) | 2020-02-04 |
| JP6086539B2 (ja) | 2017-03-01 |
| JP2013545819A (ja) | 2013-12-26 |
| CN103402543B (zh) | 2015-09-16 |
| RU2734128C2 (ru) | 2020-10-13 |
| IL226977A (en) | 2017-01-31 |
| RU2618456C2 (ru) | 2017-05-03 |
| CN103402543A (zh) | 2013-11-20 |
| ES2565353T3 (es) | 2016-04-04 |
| MX337364B (es) | 2016-02-29 |
| HK1190643A1 (zh) | 2014-07-11 |
| US20140031366A1 (en) | 2014-01-30 |
| CA2821823C (en) | 2019-05-07 |
| NZ613167A (en) | 2015-09-25 |
| BR112013015085A8 (pt) | 2018-04-03 |
| BR112013015085A2 (pt) | 2016-08-09 |
| RU2013132703A (ru) | 2015-01-27 |
| US20190240216A1 (en) | 2019-08-08 |
| WO2012083138A2 (en) | 2012-06-21 |
| EP2651450A2 (en) | 2013-10-23 |
| EP2651450A4 (en) | 2014-07-09 |
| DK2651450T3 (en) | 2016-03-14 |
| WO2012083138A3 (en) | 2012-11-01 |
| RU2016149770A (ru) | 2018-11-05 |
| JP2017114869A (ja) | 2017-06-29 |
| AU2011343576A1 (en) | 2013-07-11 |
| JP6529527B2 (ja) | 2019-06-12 |
| MX2013006816A (es) | 2013-11-01 |
| CA2821823A1 (en) | 2012-06-21 |
| AU2011343576B2 (en) | 2016-09-08 |
| EP2651450B1 (en) | 2015-12-16 |
| US10307418B2 (en) | 2019-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2651450B1 (en) | Azole pharmaceutical formulations for parenteral administration and methods for preparing and using the same as treatment of diseases sensitive to azole compounds | |
| KR101593579B1 (ko) | 치료용 조성물 | |
| US20160296622A1 (en) | Formulations of bendamustine | |
| JP2013535422A (ja) | 置換β−シクロデキストリンにより安定化されたポサコナゾール静脈注射用溶液製剤 | |
| CN102740833A (zh) | 吉西他滨衍生物的肠胃外制剂 | |
| EP3388055A1 (en) | Method for preparing liposome | |
| JP2019501861A (ja) | 水不溶性またはわずかに水溶性の薬剤の水可溶性を改善するための方法 | |
| JP5860468B2 (ja) | シクロスポリンエマルジョン | |
| JP7770688B2 (ja) | リポソームカンナビノイドおよびその使用 | |
| CN118845648B (zh) | 一种瑞普洛莎纳米胶束组合物及其制备方法和用途 | |
| AU2011302885B2 (en) | Non-aqueous oily injectable formulation exhibiting preservative efficacy | |
| JP2948111B2 (ja) | 経口投与用油性組成物 | |
| US20090253712A1 (en) | Aqueous solvent system for solubilization of azole compounds | |
| US20030082229A1 (en) | Parenteral chlorambucil for treatment of malignant and autoimmune disease and methods of use | |
| HK1190643B (en) | Azole pharmaceutical formulations for parenteral administration and methods for preparing and using the same as treatment of diseases sensitive to azole compounds | |
| US20250114342A1 (en) | Apixaban oral liquid dosage forms | |
| WO2016079749A2 (en) | Process for preparation of parenteral formulation of anidulafungin | |
| CN119789850A (zh) | 包含异维甲酸的药物组合物及其制备方法和用途 |