Bifonazole Basic information

Product Name:

Bifonazole

Synonyms:

Bifonazole for system suitability; Bifonazole Impurity; bifonazol;
Biphenylylbenzylazole; trifonazole; 1-[phenyl-(4-phenylphenyl)-methyl]imidazole;
1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE;
1[4,ALPHA-DIPHENYLBENZYL]-IMIDAZOLE

CAS:

60628-96-8

MF:

C22H18N2

MW:

310.4

EINECS:

262-336-6

Product Categories:

API;SARAFLOX

Mol File:

60628-96-8.mol

Bifonazole Chemical Properties

Melting point 

142℃

Boiling point 

440.55°C (rough estimate)

density 

1.1150 (rough estimate)

refractive index 

1.7620 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in DMSO

form 

powder

pka

6.55±0.22(Predicted)

color 

white to off-white

Merck 

14,1213

CAS Data

60628-96-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

1

RTECS 

NI3517000

HS Code 

29332900

Toxicity

LD50 in male mice, rats (mg/kg): 2629, 2854 orally (Schlüter)

Bifonazole Usage And Synthesis

Description

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.

Description

Bifonazole is a topically-active imidazole antifungal compound that has broad spectrum activity in vitro against dermatophytes, molds, yeasts, dimorphic fungi, and some Gram-positive bacteria. It is effective in the treatment of experimental dermatophytic and Candida in animals. Bifonazole is also a potent inhibitor of cytochrome P450 aromatase (K_i = 68 nM, IC₅₀ = 270 nM), which catalyzes the biosynthesis of estrogens from androgens. When applied topically in animals, it demonstrates prolonged retention time in skin with minimal percutaneous absorption, thus minimizing its effect on aromatase.

Chemical Properties

White or almost white, crystalline powder.

Originator

Bayer (W. Germany)

Uses

Bifonazole is an imidazole antifungal agent and calmodulin antagonist. It causes a reduction in glycolysis and ATP levels in B16 melanoma cells. Bifonazole is an inhibitor of C14orf1. Bifonazole is an imidazole-based anti-fungal agent with broad spectrum activity against many fungi, molds, yeast and some gram-positive bacteria. Bifonazole inhibits ergosterol biosynthetic protein 28 and Cytochrome P450 2B4.

Uses

antibacterial

Manufacturing Process

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.

Brand name

Mycospor (Bayer).

Therapeutic Function

Antifungal