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
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
| 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 | ( + / - ) |
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
Sources: https://books.google.ru/books?id=hl9f6KOon5oC&printsec=frontcover&hl=ru#v=onepage&q&f=false
Curator's Comment: # Bayer
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1978 |
270.0 nM [IC50] | ||
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | BIFONAZOLE Approved UseBifonazole 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 |
|---|---|---|
| Bifonazole (Mycospor cream) in the treatment of moccasin-type tinea pedis. Comparison between combination therapy of bifonazole cream + 10% urea ointment (Urepearl) and occlusive dressing therapy with the same agents. | 2000 |
|
| Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis. | 2001 Jun 15 |
|
| Bifonazole modulates death of cultured cerebellar granular cells induced by glutamate and oxygen-glucose deprivation. | 2001 Nov |
|
| Mechanism of bifonazole-induced [Ca2+]i increases in MDCK renal tubular cells. | 2001 Sep 30 |
|
| [A case of primary pyoderma-like aspergillosis occurring in a patient with a cervical spinal cord injury]. | 2002 |
|
| Fungicidal activities of commonly used disinfectants and antifungal pharmaceutical spray preparations against clinical strains of Aspergillus and Candida species. | 2002 Apr |
|
| Assessing pregnancy risks of azole antifungals using a high throughput aromatase inhibition assay. | 2002 Aug |
|
| [Therapeutic effects of bifonazole gel on tinea versicolor in infants: analysis of 22 cases]. | 2002 Dec |
|
| Topical treatment of tinea capitis in a neonate. | 2002 Feb |
|
| Skin infection due to Geomyces pannorum var. pannorum. | 2003 |
|
| Efficacy of flutrimazole 1% powder in the treatment of tinea pedis. | 2003 Apr |
|
| Determination of bifonazole in creams containing methyl- and propyl p-hydroxybenzoate by derivative spectrophotometric method. | 2003 Sep 15 |
|
| Actin gene-targeted RT-PCR could be a useful method for evaluating in vitro fungicidal activity against dermatophytes. | 2003 Sep-Oct |
|
| KNQ1, a Kluyveromyces lactis gene encoding a drug efflux permease. | 2004 Feb |
|
| Evaluation of the anti-Trichophyton activity of a prodigiosin analogue produced by gamma-proteobacterium, using stratum corneum epidermis of the Yucatan micropig. | 2005 Jun |
|
| Comparison of lanosterol-14 alpha-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles. | 2006 Nov 10 |
|
| Topical fenticonazole in dermatology and gynaecology: current role in therapy. | 2008 |
|
| Sulfonamide-1,2,4-triazole derivatives as antifungal and antibacterial agents: synthesis, biological evaluation, lipophilicity, and conformational studies. | 2008 Feb 1 |
|
| [Guidelines for diagnosis and treatment of mucocutaneous candidiasis]. | 2009 |
|
| In vitro susceptibility of nondermatophyte molds isolated from onycomycosis to antifungal drugs. | 2009 Aug |
|
| [Cutaneous infection caused by Alternaria alternata in an immunocompetent host]. | 2009 Jan |
|
| Susceptibility testing of amorolfine, bifonazole and ciclopiroxolamine against Trichophyton rubrum in an in vitro model of dermatophyte nail infection. | 2009 Nov |
|
| Sulfonamide-1,2,4-thiadiazole derivatives as antifungal and antibacterial agents: synthesis, biological evaluation, lipophilicity, and conformational studies. | 2010 Feb |
|
| A New Validated HPLC Method for the Simultaneous Determination of 2-phenoxyethanol, Methylparaben, Ethylparaben and Propylparaben in a Pharmaceutical Gel. | 2010 Jul |
|
| Prevention and treatment of intertrigo in large skin folds of adults: a systematic review. | 2010 Jul 13 |
|
| Association of high-dose bifonazole administration during early pregnancy and severe limb reduction defects in the newborn. | 2010 Mar |
|
| (Biphenyl-4-yl)(phen-yl)methanone. | 2010 Mar 27 |
Patents
Sample Use Guides
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
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
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ACTIVE MOIETY |
