1529. Butoconazole

Nomenclature

CAS number: 64872-76-0
1-[4-(4-Chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1H-imidazole.
C19H17Cl3N2S; mol wt 411.78.
C 55.42%, H 4.16%, Cl 25.83%, N 6.80%, S 7.79%.

Description and references

Imidazole derivative with antifungal properties. Prepn: K. A. M. Walker, US 4078071 (1978 to Syntex). Prepn, toxicity, activity vs Candida albicans in mice: K. A. M. Walker et al., J. Med. Chem. 21, 840 (1978). In vitro comparison with other antifungal agents: F. C. Odds et al., J. Antimicrob. Chemother. 14, 105 (1984). Clinical trials in treatment of vulvovaginal candidiasis: W. Droegemueller et al., Obstet. Gynecol. 64, 530 (1984); J. B. Jacobson et al., Acta Obstet. Gynecol. Scand. 64, 241 (1985). Comparison with miconazole, q.v.: C. S. Bradbeer et al., Genitourin. Med. 61, 270 (1985).

Chemical structure

Properties

Crystals from cyclohexane, mp 68-70.5°.

Derivative

Nitrate.

Nomenclature

CAS number: 64872-77-1
RS-35887; Femstat (Syntex); Gynomyk (Cassenne).
C19H17Cl3N2S.HNO3; mol wt 474.79.
C 48.06%, H 3.82%, Cl 22.40%, N 8.85%, S 6.75%, O 10.11%.

Properties

Colorless blades from acetone/ethyl acetate, mp 162-163°. LD50 in mice, male, female rats (mg/kg): >3200, >3200, 1720 orally; >1600, 940, 940 i.p. (Walker).

Therapeutic Category

Antifungal (topical).

Keywords

Antifungal (Synthetic); Imidazoles