BIFONAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H18N2
Molecular Weight	310.3917
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1=CN(C=N1)C(C2=CC=CC=C2)C3=CC=C(C=C3)C4=CC=CC=C4

InChI

InChIKey=OCAPBUJLXMYKEJ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H18N2
Molecular Weight	310.3917
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6396116 | https://www.ncbi.nlm.nih.gov/pubmed/2670516 | https://www.ncbi.nlm.nih.gov/pubmed/6372801

Bifonazole, a substituted imidazole, is a broad-spectrum antimycotic, interferes with sterol biosynthesis. Bifonazole possesses a sequential mode of action, namely inhibition of cytochrome P450-dependent C14-demethylation of sterols and direct inhibition of HMG-CoA-reductase. It possesses a broad spectrum of activity in vitro against dermatophytes, moulds, yeasts, dimorphic fungi and some Gram-positive bacteria. Bifonazole is an effective and well-tolerated treatment for superficial fungal infections of the skin.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 19A1 39 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25243857	Inhibitor 8297		270.0 nM [IC50]
Cytochrome P450 51 28 Target ID: CHEMBL1780 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2561184 \| https://www.ncbi.nlm.nih.gov/pubmed/6396116 \| https://www.ncbi.nlm.nih.gov/pubmed/6372801	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Fungal skin infections 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6372801 https://www.ncbi.nlm.nih.gov/pubmed/2670516 https://www.ncbi.nlm.nih.gov/pubmed/6683530	Curative		Approved 8429	BIFONAZOLE Approved Use Bifonazole Cream is used to treat fungal skin infections such as ringworm, athlete’s foot and fungal sweat rash. The active substance in Canesten Bifonazole Cream is bifonazole. Bifonazole belongs to a group of medicines called imidazoles and is an antifungal agent which fights the cause of fungal skin infections.

PubMed

Title	Date	PubMed
In vitro studies of activities of some antifungal agents against Candida albicans ATCC 10231 by the turbidimetric method.	1992 Apr	1503456
Comparative efficacies of commonly used disinfectants and antifungal pharmaceutical spray preparations against dermatophytic fungi.	2001 Aug	11556761
[In vitro susceptibility of dematiaceous fungi to ten antifungal drugs using an agar diffusion test].	2001 Sep	15487919
Synthesis and biological evaluation of azole derivatives, analogues of bifonazole, with a phenylisoxazolyl or phenylpyrimidinyl moiety.	2001 Sep	11680806
A novel method using micropig stratum corneum in vitro for the evaluation of anti-Trichophyton mentagrophytes activity.	2002	12363015
[A case of primary pyoderma-like aspergillosis occurring in a patient with a cervical spinal cord injury].	2002	11865295
Susceptibility testing of Malassezia pachydermatis using the urea broth microdilution method.	2002 Apr	12000506
Experimental tinea unguium model to assess topical antifungal agents using the infected human nail with dermatophyte in vitro.	2002 Dec	12525893
Determination of bifonazole in creams containing methyl- and propyl p-hydroxybenzoate by derivative spectrophotometric method.	2003 Sep 15	12946540
Actin gene-targeted RT-PCR could be a useful method for evaluating in vitro fungicidal activity against dermatophytes.	2003 Sep-Oct	14587308
In vitro susceptibility testing of dermatophytes: comparison of disk diffusion and reference broth dilution methods.	2004 Apr	15062918
Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors.	2004 Apr 15	15135088
Comparative assessment of the inhibition of recombinant human CYP19 (aromatase) by azoles used in agriculture and as drugs for humans.	2004 Aug	15554355
In vitro antifungal activity of luliconazole (NND-502), a novel imidazole antifungal agent.	2004 Aug	15365862
Synthesis, antimicrobial activity and molecular modeling studies of halogenated 4-[1H-imidazol-1-yl(phenyl)methyl]-1,5-diphenyl-1H-pyrazoles.	2004 Oct 15	15388173
Difference in percutaneous absorption and intracutaneous distribution in guinea pigs among topical antifungal drugs (tioconazole solution, tioconazole cream, miconazole nitrate solution and bifonazole solution).	2004 Sep	15340231
High-performance thin-layer chromatography determination of some antimycotic imidazole derivatives and preservatives in medicinal creams and a gel.	2005 Sep-Oct	16386007
Decreased susceptibility to antifungals in respiratory-deficient Kluyveromyces lactis mutants.	2007	18298045
Thermodynamic fidelity of the mammalian cytochrome P450 2B4 active site in binding substrates and inhibitors.	2008 Mar 14	18241887
Seborrhoeic dermatitis.	2010 Dec 7	21418692
Sulfonamide-1,2,4-thiadiazole derivatives as antifungal and antibacterial agents: synthesis, biological evaluation, lipophilicity, and conformational studies.	2010 Feb	20118573
(Biphenyl-4-yl)(phen-yl)methanone.	2010 Mar 27	21580736

Patents

Sample Use Guides

In Vivo Use Guide

Bifonazole 1% w/w Cream. The cream should be applied thinly and evenly to the affected areas once daily, preferably at night before going to bed, and rubbed in gently. Treatment should be continued for 2-3 weeks, depending on the type of infection.

Route of Administration: Transdermal

In Vitro Use Guide

Concentrations of less than or equal to 5 ug/ml bifonazole have a fungicidal effect on dermatophytes, and a MIC value of less than or equal to 0.25 ug/ml has a maximal effect on Torulopsis glabrata. In ng concentrations bifonazole is effective on proliferating dermatophytes and pseudomycelia of Candida albicans.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:45:15 GMT 2023` Edited by `admin` on `Sat Dec 16 17:45:15 GMT 2023`
Record UNII	QYJ305Z91O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIFONAZOLE

Official Name

English

(±)-1-(P,.ALPHA.-DIPHENYLBENZYL)IMIDAZOLE

Common Name

English

BIFONAZOLE [MART.]

Common Name

English

bifonazole [INN]

Common Name

English

BIFONAZOLE [EP MONOGRAPH]

Common Name

English

Bifonazole [WHO-DD]

Common Name

English

BAY-H-4502

Code

English

1H-IMIDAZOLE, 1-((1,1'-BIPHENYL)-4-YLPHENYLMETHYL)-, (±)-

Systematic Name

English

BIFONAZOLE [JAN]

Common Name

English

NSC-758954

Code

English

BIFONAZOLE [MI]

Common Name

English

BIFONAZOLE [EP IMPURITY]

Common Name

English

BAY H 4502

Code

English

BIFONAZOLE [USAN]

Common Name

English

D01AC10

Code

English

1-((4-BIPHENYLYL)-PHENYLMETHYL)-1H-IMIDAZOLE

Systematic Name

English

MYCOSPOR

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514