Butoconazole
Butoconazole (trade names Gynazole-1, Mycelex-3) is an imidazole antifungal used in gynecology. It is administered as a vaginal cream.[1][2]
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Trade names | Gynazole-1, Mycelex-3 |
AHFS/Drugs.com | Monograph |
MedlinePlus | a682012 |
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Routes of administration | Vaginal cream |
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Formula | C19H17Cl3N2S |
Molar mass | 411.776 g/mol g·mol−1 |
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Synthesis
Reaction of epichlorohydrin with 4-chlorophenylbenzylmganeium chloride leads to 1-chloro-4-(4-chlorophenyl)butan-2-ol (3). Displacement with sodium imidazole, conversion of the secondary alcohol to the chloride (SOCl2), and displacement with 2,6-dichlorobenzenethiol concludes the synthesis of the antifungal butoconazole.
References
- Seidman, L. S.; Skokos, C. K. (2005). "An evaluation of butoconazole nitrate 2% site release vaginal cream (Gynazole-1) compared to fluconazole 150 mg tablets (Diflucan) in the time to relief of symptoms in patients with vulvovaginal candidiasis". Infectious Diseases in Obstetrics and Gynecology. 13 (4): 197–206. doi:10.1080/10647440500240615 (inactive 2019-08-20). PMC 1784583. PMID 16338779.
- Butoconazole Monograph
- Walker, Keith A. M.; Braemer, Allen C.; Hitt, Sharon; Jones, Richard E.; Matthews, Thomas R. (1978). "1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl]-1H-imidazole nitrate, a new potent antifungal agent". Journal of Medicinal Chemistry. 21 (8): 840–3. doi:10.1021/jm00206a028. PMID 357722.
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