2368. Cloconazole

Nomenclature

CAS number: 77175-51-0
1-[1-[2-[(3-Chlorophenyl)methoxy]phenyl]ethenyl]-1H-imidazole; 1-[1-[2-[(3-chlorobenzyl)oxy]phenyl]vinyl]-1H-imidazole; croconazole.
C18H15ClN2O; mol wt 310.78.
C 69.56%, H 4.86%, Cl 11.41%, N 9.01%, O 5.15%.

Description and references

Antimycotic vinylimidazole. Prepn and antifungal properties: M. Ogata et al., BE 883665; eidem, US 4328348 (1980, 1982 both to Shionogi); eidem, J. Med. Chem. 26, 768 (1983). Pharmacology: K. Yamamoto et al., Oyo Yakuri 27, 533 (1984), C.A. 101, 16881c (1984). Series of articles on metabolism in rats and rabbits: K. Mizojiri et al., Iyakuhin Kenkyu 16, 177-206 (1985), C.A. 103, 47788y; 47789z; 47790t (1985). Mechanism of action study: T. Hiratani, H. Yamaguchi, Chemotherapy (Tokyo) 33, 579 (1985).

Chemical structure

Properties

mp 72-73°. Sol in ethyl acetate.

Derivative

Monohydrochloride.

Nomenclature

CAS number: 77174-66-4
710674-S; Pilzcin (Shionogi).
C18H15ClN2O.HCl; mol wt 347.24.
C 62.26%, H 4.64%, Cl 20.42%, N 8.07%, O 4.61%.

Properties

Crystals from ethyl acetate + acetonitrile, mp 148.5-150°. LD50 in rats (mg/kg): 7000 s.c.; 2500 orally (Ogata, 1983).

Therapeutic Category

Antifungal (topical).

Keywords

Antifungal (Synthetic); Imidazoles