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Title: Ketoconazole
CAS Registry Number: 65277-42-1
CAS Name: cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine
Manufacturers' Codes: R-41400
Trademarks: Fungarest (Janssen); Fungoral (Janssen); Ketoderm (Janssen); Ketoisdin (Isdin); Nizoral (Janssen); Orifungal M (Janssen); Panfungol (Esteve)
Molecular Formula: C26H28Cl2N4O4
Molecular Weight: 531.43
Percent Composition: C 58.76%, H 5.31%, Cl 13.34%, N 10.54%, O 12.04%
Literature References: Orally active, broad-spectrum antimycotic. Prepn: J. Heeres et al., DE 2804096, eidem, US 4144346 and US 4223036 (1978, 1979, 1980, all to Janssen); eidem, J. Med. Chem. 22, 1003 (1979). Pharmacokinetics: E. W. Gascoigne et al., Clin. Res. Rev. 1, 177 (1981); C. Brass et al., Antimicrob. Agents Chemother. 21, 151 (1982). HPLC determn in human serum: V. L. Pascucci et al., J. Pharm. Sci. 72, 1467 (1983). Series of articles on animal and human studies: Rev. Infect. Dis. 2, 519-692 (1980). Effect on hepatic enzymes in vitro and in vivo: K. N. Buchi et al., Biochem. Pharmacol. 35, 2845 (1986); J. K. Ritter, M. R. Franklin, Toxicol. Lett. 36, 51 (1987). Case reports of hepatic toxicity: J. K. Heiberg, E. Svejgaard, Br. Med. J. 283, 825 (1981); R. Rollman, L. Loof, Br. J. Dermatol. 108, 376 (1983). Controlled clinical trials: E. A. Petersen et al., Ann. Intern. Med. 93, 791 (1980); W. T. Hughes et al., J. Infect. Dis. 147, 1060 (1983); H. W. Jolly et al., Cutis 31, 208 (1983). Clinical evaluation as inhibitor of steroid synthesis: N. Sonino, N. Engl. J. Med. 317, 812 (1987). Review of pharmacology and therapeutic efficacy: C. A. Sohn, Clin. Pharm. 1, 217 (1982); R. C. Heel et al., Drugs 23, 1-36 (1982). Series of articles on clinical efficacy and therapeutic experience: Drugs Exp. Clin. Res. 12, 397-427 (1986).
Properties: Crystals from 4-methyl-2-pentanone, mp 146¡ã. LD50 in mice, rats, guinea pigs, dogs (mg/kg): 44, 86, 28, 49 i.v.; 702, 227, 202, 780 orally (Heel).
Melting point: mp 146¡ã
Toxicity data: LD50 in mice, rats, guinea pigs, dogs (mg/kg): 44, 86, 28, 49 i.v.; 702, 227, 202, 780 orally (Heel)
Therap-Cat: Antifungal.
Keywords: Antifungal (Synthetic); Imidazoles.
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