| Identification | More | [Name]
Bifonazole | [CAS]
60628-96-8 | [Synonyms]
1[4,ALPHA-DIPHENYLBENZYL]-IMIDAZOLE
1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE
1-[phenyl-(4-phenylphenyl)-methyl]imidazole
BIFONAZOLE
mycospor
1-((1,1’-biphenyl)-4-ylphenylmethyl)-1h-imidazol
1-((4-biphenylyl)phenylmethyl)-1h-imidazole
1-(alpha-(4-biphenylyl)benzyl)-imidazol
1-(alpha-(4-biphenylyl)benzyl)imidazole
1-[(1,1’-biphenyl)-4-ylphenylmethyl]-1H-Imidazole
bayh4502
bifonazol
Biphenylylbenzylazole
trifonazole
1-(p,α-diphenylbenzyl)imidazole
BIFONAZOLE(PATENT-NOSUPPLY)
1-[α-(4-biphenyl)benzyl]-1H-imidazole
1H-Imidazole, 1-([1,1'-biphenyl]-4-ylphenylmethyl)-
Amycor
A-One-L | [EINECS(EC#)]
262-336-6 | [Molecular Formula]
C22H18N2 | [MDL Number]
MFCD00865567 | [Molecular Weight]
310.39 | [MOL File]
60628-96-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White or almost white, crystalline powder. | [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 | [Cosmetics Ingredients Functions]
ANTI-SEBORRHEIC
ANTIMICROBIAL | [InChI]
InChI=1S/C22H18N2/c1-3-7-18(8-4-1)19-11-13-21(14-12-19)22(24-16-15-23-17-24)20-9-5-2-6-10-20/h1-17,22H | [InChIKey]
OCAPBUJLXMYKEJ-UHFFFAOYSA-N | [SMILES]
C(C1C=CC=CC=1)(N1C=NC=C1)C1C=CC(C2C=CC=CC=2)=CC=1 | [LogP]
4.770 | [CAS DataBase Reference]
60628-96-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [WGK Germany ]
1
| [RTECS ]
NI3517000
| [HS Code ]
29332900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral | [Toxicity]
LD50 in male mice, rats (mg/kg): 2629, 2854 orally (Schlüter) |
| Hazard Information | Back Directory | [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. | [Chemical Properties]
White or almost white, crystalline powder. | [Originator]
Bayer (W. Germany) | [Uses]
antibacterial | [Definition]
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. | [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 | [References]
[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 |
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