8465. Sertaconazole
Nomenclature
CAS number: 99592-32-2
1-[2-[(7-Chlorobenzo[b]thien-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole; (±)-1-[2,4-dichloro-β-[(7-chlorobenzo[b]thien-3-yl)methoxy]phenethyl]imidazole; 7-chloro-3-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy-methyl]benzo[b]thiophene; FI-7045. C20H15Cl3N2OS; mol wt 437.77.
C 54.87%, H 3.45%, Cl 24.30%, N 6.40%, O 3.65%, S 7.32%.
Description and references
Prepn: R. Foguet et al., EP 151477; eidem, US 5135943 (1985, 1992 both to Ferrer). Synthesis, antifungal activity, pharmacology, toxicology and clinical evaluations: Arzneimittel-Forsch. 42, 689-774 (1992). Physical props: C. Albet et al., ibid. 695. HPLC determn: eidem, J. Pharm. Biomed. Anal. 10, 205 (1992).
Properties
mp 146-147°.Derivative
Nitrate.Nomenclature
CAS number: 99592-39-9
FI-7056; Dermofix (Ferrer); Zalain (Robert). C20H15Cl3N2OS.HNO3; mol wt 500.78.
C 47.97%, H 3.22%, Cl 21.24%, N 8.39%, O 12.78%, S 6.40%.
Properties
Odorless, white crystalline powder, mp 158-160°. Fairly sol in ethanol (1.7%); chloroform (1.5%); slightly sol in acetone (0.95%); very slightly sol in n-octanol (0.069%). Practically insol in water (<0.01%). pKb: 7.26. uv max (methanol): 302.3 (A1cm1% 79.8), 292.9, 260.3 nm.Therapeutic Category
Antifungal.
Keywords
Antifungal (Synthetic); Imidazoles