Structural Formula Vector Image
Title: Fluconazole
CAS Registry Number: 86386-73-4
CAS Name: a-(2,4-Difluorophenyl)-a-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol
Additional Names: 2,4-difluoro-a,a-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol; 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
Manufacturers' Codes: UK-49858
Trademarks: Biozolene (Bioindustria); Diflucan (Pfizer); Elazor (Sigma-Tau); Triflucan (Pfizer)
Molecular Formula: C13H12F2N6O
Molecular Weight: 306.27
Percent Composition: C 50.98%, H 3.95%, F 12.41%, N 27.44%, O 5.22%
Literature References: Orally active bistriazole antifungal agent. Prepn: K. Richardson, GB 2099818; idem, US 4404216 (1982, 1983 both to Pfizer). Antifungal activity in vivo: K. Richardson et al., Antimicrob. Agents Chemother. 27, 832 (1985); and in vitro: T. E. Rogers, J. N. Galgiani, ibid. 30, 418 (1986). Pharmacokinetics: M. J. Humphrey et al., ibid. 28, 648 (1985). GC determn in human plasma and urine: P. R. Wood, M. H. Tarbit, J. Chromatogr. 383, 179 (1986). Evaluation as maintenance therapy for cryptococcal meningitis in AIDS patients: S. A. Bozzette et al., N. Engl. J. Med. 324, 580 (1991). Symposium on mode of action, toxicology, animal models and clinical studies: International Telesymposium on Recent Trends in the Discovery, Development and Evaluation of Antifungal Agents Section 2, R. A. Fromtling, Ed. (J. R. Prous Science Publ., Barcelona, 1987) pp 77-174. Infection prophylaxis in bone marrow transplantation patients: M. L. MacMillan et al., Am. J. Med. 112, 369 (2002).
Properties: Crystals from ethyl acetate/hexane, mp 138-140°.
Melting point: mp 138-140°
Derivative Type: Dihydrogen phosphate ester
CAS Registry Number: 194798-83-9
Additional Names: Fosfluconazole; 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propyl dihydrogen phosphate
Trademarks: Prodif (Pfizer)
Molecular Formula: C13H13F2N6O4P
Molecular Weight: 386.25
Percent Composition: C 40.42%, H 3.39%, F 9.84%, N 21.76%, O 16.57%, P 8.02%
Literature References: Prepn: C. W. Murtiashaw et al., WO 9728169; S. Green et al., US 6790957 (1997, 2004 both to Pfizer). Review of discovery and commercial process development: A. Bentley et al., Org. Process Res. Dev. 6, 109-112 (2002).
Properties: Water-soluble prodrug. White powder, mp 223-224°.
Melting point: mp 223-224°
Therap-Cat: Antifungal.
Keywords: Antifungal (Synthetic); Triazoles.

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