Butoconazole

Butoconazole
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
ATC code	G01AF15 (WHO) ;
Legal status
Legal status	US: OTC ;
Identifiers
	IUPAC name (RS)-1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole;
CAS Number	67085-13-6 ;
PubChem CID	47472;
DrugBank	DB00639 ;
ChemSpider	43192 ;
UNII	0Q771797PH;
KEGG	D00880 ;
ChEBI	CHEBI:3240 ;
ChEMBL	ChEMBL1295 ;
CompTox Dashboard (EPA)	DTXSID2048537 ;
Chemical and physical data
Formula	C19H17Cl3N2S
Molar mass	411.776 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:SWLMUYACZKCSHZ-UHFFFAOYSA-N ;
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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

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

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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[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 2019-08-20). 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.