1213. Bifonazole

Nomenclature

CAS number: 60628-96-8
1-([1,1′-Biphenyl]-4-ylphenylmethyl)-1H-imidazole; (±)-1-(p,α-diphenylbenzyl)imidazole; Bay h 4502; Amycor (Lipha); Azolmen (Menarini); Bedriol (Andromaco); Mycospor (Bayer); Mycosporan (Bayer).
C22H18N2; mol wt 310.39.
C 85.13%, H 5.85%, N 9.03%.

Description and references

Antimycotic deriv of imidazole. Prepn: E. Regel et al., DE 2461406; eidem, US 4118487 (1976, 1978 both to Bayer). Series of articles on in vitro and in vivo antimycotic efficacy, microscopic studies, pharmacokinetics, efficacy in dermatomycoses and comparison with clotrimazole and miconazole, q.q.v.: Arzneim.-Forsch. 33, 517-551, 745-754 (1983). Toxicology: G. Schlüter, ibid. 739.

Chemical structure

Properties

Crystals from acetonitrile, mp 142°. Very lipophilic. Sol in alcohols, DMF, DMSO. Soly in water at pH 6: <0.1 mg/100 ml. Stable in aq soln at pH 1-12. LD50 in male mice, rats (mg/kg): 2629, 2854 orally (Schlüter).

Therapeutic Category

Antifungal.

Keywords

Antifungal (Synthetic); Imidazoles