ChemicalBook > CAS DataBase List > Bifonazole

Bifonazole

Product Name
Bifonazole
CAS No.
60628-96-8
Chemical Name
Bifonazole
Synonyms
mycospor;bifonazol;1-[phenyl-(4-phenylphenyl)-methyl]imidazole;Amycor;Bedrid;A-One-L;Azolmen;Bedriol;Bifazol;bayh4502
CBNumber
CB8138176
Molecular Formula
C22H18N2
Formula Weight
310.4
MOL File
60628-96-8.mol
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Bifonazole Property

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
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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0001421
Product name
Bifonazole for system suitability
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
10 mg
Price
$228
Updated
2025/07/31
Sigma-Aldrich
Product number
B3563
Product name
Bifonazole
Purity
≥98% (HPLC)
Packaging
10mg
Price
$55.8
Updated
2025/07/31
Sigma-Aldrich
Product number
B3563
Product name
Bifonazole
Purity
≥98% (HPLC)
Packaging
50mg
Price
$214
Updated
2025/07/31
Sigma-Aldrich
Product number
B1110000
Product name
Bifonazole
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
50 mg
Price
$159
Updated
2025/07/31
TCI Chemical
Product number
B4173
Product name
Bifonazole
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$34
Updated
2025/07/31
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Bifonazole Chemical Properties,Usage,Production

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 (Ki = 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

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

Bifonazole Preparation Products And Raw materials

Raw materials

Biphenyl 2,2'-Bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole

Preparation Products

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Bifonazole Suppliers

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View Lastest Price from Bifonazole manufacturers

Hefei Lbao Physical & Chemical Science Co.,Ltd
Product
Bifonazole 60628-96-8
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
Customise
Release date
2025-11-21
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Bifonazole 60628-96-8
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98%-100.5%
Supply Ability
1000kg
Release date
2021-07-29
Hebei Chuanghai Biotechnology Co., Ltd
Product
Bifonazole 60628-96-8
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100 mt
Release date
2024-11-13

60628-96-8, BifonazoleRelated Search:

FIREMASTER BP-6 Imidazole Benzyltriethylammonium chloride 5-Chlorovaleric acid Pralmorelin DL-α-Tocopherol Bensulfuron methyl Bifendate trans-Bifenthtin Methylparaben PHENYL VALERATE Methyl acrylate 4-(Diethylamino)salicylaldehyde Diphenolic acid Kresoxim-methyl Thiophanate-methyl 2,3,3',4,4',5-HEXACHLOROBIPHENYL 1H-Imidazole, 4-([1,1'-biphenyl]-4-ylphenylmethyl)-

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