Butoconazole

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Butoconazole
Butoconazole.svg
Systematic (IUPAC) name
1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole
Clinical data
Trade names Gynazole-1, Mycelex-3
AHFS/Drugs.com Monograph
MedlinePlus a682012
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Vaginal cream
Legal status
Legal status
Identifiers
CAS Number 67085-13-6 YesY
ATC code G01AF15 (WHO)
PubChem CID 47472
DrugBank DB00639 YesY
ChemSpider 43192 YesY
UNII 0Q771797PH YesY
KEGG D00880 N
ChEBI CHEBI:3240 YesY
ChEMBL CHEMBL1295 YesY
Chemical data
Formula C19H17Cl3N2S
Molar mass 411.776 g/mol
 NYesY (what is this?)  (verify)

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 2016-05-14). 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. doi:10.1021/jm00206a028. PMID 357722.