6846. Omoconazole

Nomenclature

CAS number: 74512-12-2
1-[(1Z)-2-[2-(4-Chlorophenoxy)ethoxy]-2-(2,4-dichlorophenyl)-1-methylethenyl]-1H-imidazole; (Z)-1-[2,4-dichloro-β-[2-(p-chlorophenoxy)ethoxy]-α-methylstyryl]imidazole; CM-8282.
C20H17Cl3N2O2; mol wt 423.72.
C 56.69%, H 4.04%, Cl 25.10%, N 6.61%, O 7.55%.

Description and references

Prepn: L. Zirngibl et al., DE 2839388; eidem, US 4210657 (both 1980 to Siegfried); and crystal structure: K. Thiele et al., Helv. Chim. Acta 70, 441 (1987). Stereospecific synthesis: L. Zirngibl, K. Thiele, US 4554356 (1985 to Siegfried). In vitro fungistatic activity: M. Mosse et al., Pathol. Biol. 34, 684 (1986).

Chemical structure

Properties

Crystals from ethyl acetate/hexane (1:4), mp 89-90°.

Derivative

Nitrate.

Nomenclature

CAS number: 83621-06-1
Sgd-12878; Afongan (Galderma); Azameno (Wyeth); Fungisan (Galderma); Fongamil (Biorga).
C20H17Cl3N2O2.HNO3; mol wt 486.73.
C 49.35%, H 3.73%, Cl 21.85%, N 8.63%, O 16.44%.

Properties

Crystals from ethyl acetate/ethanol, mp 118-120° (Büchi), 122.5° (Mettler).

Therapeutic Category

Antifungal (topical).

Keywords

Antifungal (Synthetic); Imidazoles