3502. Econazole

Nomenclature

CAS number: 27220-47-9
1-[2-[(4-Chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole; 1-[2,4-dichloro-β-[(p-chlorobenzyl)oxy]phenethyl]imidazole; SQ-13050.
C18H15Cl3N2O; mol wt 381.68.
C 56.64%, H 3.96%, Cl 27.87%, N 7.34%, O 4.19%.

Description and references

Prepn: Godefroi et al., J. Med. Chem. 12, 784 (1969); Godefroi, Heeres, DE 1940388; eidem, US 3717655 (1970, 1973 both to Janssen). Biological and toxicological properties: Thienpont et al., Arzneim.-Forsch. 25, 224 (1975). Review of antifungal activity and therapeutic efficacy: R. C. Heel et al., Drugs 16, 177-201 (1978). Comprehensive description: A. M. Dyas, H. Delargy, Anal. Profiles Drug Subs. Excip. 23, 125-152 (1994).

Chemical structure

Properties

mp 86.8°.

Derivative

Nitrate.

Nomenclature

CAS number: 24169-02-6
R-14827; Epi-Pevaryl (Cilag-Chemie); Gyno-Pevaryl (Cilag-Chemie); Ifenec (Italfarmaco); Micofugal (Biopharma); Micogin (Crosara); Palavale (Otsuka); Pargin (Gibipharma); Pevaryl (Cilag); Spectazole (Ortho).
C18H15Cl3N2O.HNO3; mol wt 444.70.
C 48.62%, H 3.63%, Cl 23.92%, N 9.45%, O 14.39%.

Properties

White, odorless crystals from a mixture of 2-propanol, methanol and diisopropyl ether, mp 162°. uv max (methanol): 202, 225 nm. uv max (methanol): 265, 271, 280 nm (A1%1cm 9.4, 9.7, 4.9). Soly at 20° (g/100 ml): water <0.1; ethanol (96%) 2.0; acetone 1.5. LD50 in mice, rats (mg/kg): 462.7, 667.7 orally (Thienpont).

Therapeutic Category

Antifungal.

Keywords

Antifungal (Synthetic); Imidazoles