Butoconazole

Butoconazole

File: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)
Legal status	US: OTC
Routes of administration	Vaginal cream
Identifiers
CAS Number	67085-13-6 Y
ATC code	G01AF15 (WHO)
PubChem	CID: 47472
DrugBank	DB00639 Y
ChemSpider	43192 Y
UNII	0Q771797PH Y
KEGG	D00880 N
ChEBI	CHEBI:3240 Y
ChEMBL	CHEMBL1295 Y
Chemical data
Formula	C19H17Cl3N2S
Molecular mass	411.776 g/mol
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)

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

Synthesis

File:Butoconazole synthesis.svg

Butoconazole synthesis: 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.