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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

Quality Level

100

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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

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
Laura Toribio et al.
Journal of separation science, 29(10), 1373-1378 (2006-08-10)
The enantiomeric separation of bifonazole by supercritical fluid chromatography on Chiralpak AD has been studied. The effect of different modifiers (methanol, ethanol, 2-propanol, and acetonitrile) was examined. Enantioseparation was possible with all of them, but the best results were provided
Di-Qing Luo et al.
Mycoses, 54(6), e780-e784 (2011-05-28)
Interdigital ulcer is an exceptionally rare condition while erosio interdigitalis blastomycetica is common for candidiasis. Four Chinese patients with Candida interdigital ulcers were reported. The exudates were examined directly and cultured for fungi. Skin biopsies were stained with haematoxylin-eosin and
Yonghong Zhao et al.
The Journal of biological chemistry, 281(9), 5973-5981 (2005-12-24)
To better understand ligand-induced structural transitions in cytochrome P450 2B4, protein-ligand interactions were investigated using a bulky inhibitor. Bifonazole, a broad spectrum antifungal agent, inhibits monooxygenase activity and induces a type II binding spectrum in 2B4dH(H226Y), a modified enzyme previously
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