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B3563

Sigma-Aldrich

Bifonazole

≥98% (HPLC)

Synonym(s):

1-(p,α-Diphenylbenzyl)imidazole

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About This Item

Empirical Formula (Hill Notation):
C22H18N2
CAS Number:
60628-96-8
Molecular Weight:
310.39
EC Number:
262-336-6
MDL number:
MFCD00865567
UNSPSC Code:
12352200
PubChem Substance ID:
329773219
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >10 mg/mL

originator

Bayer

storage temp.

room temp

SMILES string

c1ccc(cc1)C(c2ccc(cc2)-c3ccccc3)n4ccnc4

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

InChI key

OCAPBUJLXMYKEJ-UHFFFAOYSA-N

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Biochem/physiol Actions

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.
Bifonazole is used to treat several infections such as onychomycoses, otomycoses, erythrasma, psoriasis, sebopsoriasis, seborrhoeic dermatitis and rosacea. Bifonazole is also used as an important drug to treat melanoma.

Features and Benefits

This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Clotrimazole and bifonazole detach hexokinase from mitochondria of melanoma cells
Penso J and Beitner R
European Journal of Pharmacology, 342(1), 113-117 (1998)
Sai Hu et al.
International journal of molecular medicine, 47(5) (2021-03-12)
Radioresistance is the predominant cause for radiotherapy failure and disease progression, resulting in increased breast cancer‑associated mortality. Using gene expression signature analysis of the Library of Integrated Network‑Based Cellular Signatures (LINCS) and Gene Expression Omnibus (GEO), the aim of the
Shinichi Watanabe et al.
Mycoses, 49(3), 236-241 (2006-05-10)
The aim of the study was to compare the efficacy and safety of luliconazole 1% cream and bifonazole 1% cream as applied in the treatment of tinea pedis (interdigital-type and plantar-type). A multi-clinic, randomised single-blind, parallel group study with 34
Nehama Linder et al.
Birth defects research. Part A, Clinical and molecular teratology, 88(3), 201-204 (2009-12-17)
Neonatal limb reduction defects may be caused by exposure to an external agent. The azole derivatives are used in the treatment of systemic and dermal mycoses. Their relative teratogenic risk is still controversial. We describe two newborns with severe limb
P Ross Wilderman et al.
The FEBS journal, 279(9), 1607-1620 (2011-11-05)
Residues located outside the active site of cytochromes P450 2B have exhibited importance in ligand binding, structural stability and drug metabolism. However, contributions of non-active-site residues to the plasticity of these enzymes are not known. Thus, a systematic investigation was
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