5357. Lanoconazole

Nomenclature

CAS number: 101530-10-3
(E)-(±)-α-[4-(2-Chlorophenyl)-1,3-dithiolan-2-ylidene]-1H-imidazole-1-acetonitrile; latoconazole; TJN-318; NND-318; Astat (Nihon Nohyaku).
C14H10ClN3S2; mol wt 319.83.
C 52.57%, H 3.15%, Cl 11.08%, N 13.14%, S 20.05%.

Description and references

Prepn: A. Soe et al., JP Kokai 85 218387; idem et al., US 4636519 (1985, 1987 both to Nihon Nohyaku). In vivo antifungal activity: H. Oka et al., Arzneim.-Forsch. 42, 345 (1992); Y. Niwano et al., Antimicrob. Agents Chemother. 38, 2204 (1994). Toxicity study: P. L. Munt et al., Oyo Yakuri 43, 195 (1992).

Chemical structure

Properties

Light yellow crystals, mp 141.5°. LD50 in male, female mice, rats (mg/kg): 3224, 2715, 993, 652 orally; 2158, 1743, 1655, 2596 i.p.; >5000 both species s.c. LD50 dermally in rats: >5000 mg/kg (Munt).

Therapeutic Category

Antifungal.

Keywords

Antifungal (Synthetic); Imidazoles