60628-96-8

Bifonazole represents the first topical broad spectrum antimycotic approved for once daily administration. Its in vitro activity appears equivalent to its structural relative clotrimazole, being effective against dermatophytes, other filamentous fungi, dimorphic fungi and yeasts.

White or almost white, crystalline powder.

Bayer (W. Germany)

antibacterial

ChEBI: 1-[biphenyl-4-yl(phenyl)methyl]imidazole is a member of the class of imidazoles carrying an alpha-(biphenyl-4-yl)benzyl substituent at position 1. It is a member of imidazoles and a member of biphenyls.

38.8g (0.15 mol) of 4-phenylbenzophenone are dissolved in 200 ml of ethanol and 39 (0.075 mol) of sodium borohydride are added. After heating for 15 hours under reflux, and allowing to cool, the reaction mixture is hydrolyzed with water containing a little hydrochloric acid. The solid thereby produced is purified by recrystallization from ethanol. 36 g (89% of theory) of (biphenyl- 4-yl)-phenyl-carbinol [alternatively named as diphenyl-phenyl carbinol or α- (biphenyl-4-yl)benzylalcohol] of melting point 72°-73°C are obtained.
13.6 g (0.2 mol) of imidazole are dissolved in 150 ml of acetonitrile and 3.5 ml of thionyl chloride are added at 10°C. 13 g (0.05 mol) of (biphenyl-4-yl)- phenyl-carbinol are added to the solution of thionyl-bis-imidazole thus obtained. After standing for 15 hours at room temperature, the solvent is removed by distillation in vacuo. The residue is taken up in chloroform and the solution is washed with water. The organic phase is collected, dried over sodium sulfate and filtered and the solvent is distilled off in vacuo. The oily residue is dissolved in ethyl acetate and freed from insoluble, resinous constituents by filtration. The solvent is again distilled off in vacuo and the residue is purified by recrystallization from acetonitrile, 8.7 g (56% of theory) of (biphenyl-4-yl)-imidazol-1-yl-phenylmethane [alternatively named as diphenyl-imidazolyl-(1)-phenyl-methane or as 1-(α-biphenyl-4- ylbenzyl)imidazole] of melting point 142°C are obtained.

Mycospor (Bayer).

Antifungal

[1] T E LACKNER  S P C. Bifonazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses.[J]. Drugs, 1989, 38 2: 204-225. DOI: 10.2165/00003495-198938020-00004
[2] FROMTLING R A. Overview of medically important antifungal azole derivatives.[J]. Clinical Microbiology Reviews, 1988, 1 2: 187-217. DOI: 10.1128/cmr.1.2.187
[3] CHINAZA EGBUTA  Debashis G  Jessica Lo. Mechanism of inhibition of estrogen biosynthesis by azole fungicides.[J]. Endocrinology, 2014, 155 12: 4622-4628. DOI: 10.1210/en.2014-1561