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
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
    CompTox Dashboard (EPA)
    Chemical and physical data
    FormulaC19H17Cl3N2S
    Molar mass411.77 g·mol−1
    3D model (JSmol)
     NY (what is this?)  (verify)

    Synthesis
    Butoconazole synthesis:[3][4]

    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
    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
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