Butoconazole

Butoconazole (trade names Gynazole-1, Mycelex-3) is an imidazole antifungal used in gynecology. It is administered as a vaginal cream.[1][2]

Butoconazole
Clinical data
Trade namesGynazole-1, Mycelex-3
AHFS/Drugs.comMonograph
MedlinePlusa682012
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Vaginal cream
ATC code
Legal status
Legal status
  • US: OTC / Rx-only
Identifiers
IUPAC name
  • (RS)-1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H17Cl3N2S
Molar mass411.77 g·mol−1
3D model (JSmol)
SMILES
  • Clc1ccc(cc1)CCC(Sc2c(Cl)cccc2Cl)Cn3ccnc3
InChI
  • InChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2 Y
  • Key:SWLMUYACZKCSHZ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Synthesis
Butoconazole synthesis:[3][4]

Reaction of epichlorohydrin with 4-Chlorobenzyl magnesium bromide 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
  1. Seidman LS, Skokos CK (December 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:10.1155/2005/453239. PMC 1784583. PMID 16338779.
  2. Butoconazole Monograph
  3. Walker KA, Braemer AC, Hitt S, Jones RE, Matthews TR (August 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.
  4. US 4078071, Walker KA, "Derivatives of substituted N-alkyl imidazoles", issued 7 March 1978, assigned to Syntex
  • "Butoconazole". Drug Information Portal. U.S. National Library of Medicine.


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