Butoconazole

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Butoconazole
Butoconazole.svg
Clinical data
Trade namesGynazole-1, Mycelex-3
AHFS/Drugs.comMonograph
MedlinePlusa682012
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Vaginal cream
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H17Cl3N2S
Molar mass411.776 g/mol
3D model (JSmol)
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Butoconazole (trade names Gynazole-1, Mycelex-3) is an imidazole antifungal used in gynecology. It is administered as a vaginal cream.[1][2]

Synthesis[edit]

Butoconazole synthesis:[3] Keith A. M. Walker U.S. Patent 4,078,071 (1978 to Syntex)

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[edit]

  1. ^ 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 2018-09-22). PMC 1784583. PMID 16338779.
  2. ^ Butoconazole Monograph
  3. ^ 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.