Identification
- Summary
Bifonazole is an azole antifungal drug used to treat fungal skin infections, such as dermatomycosis.
- Generic Name
- Bifonazole
- DrugBank Accession Number
- DB04794
- Background
Bifonazole is an azole antifungal drug.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Bifonazole (DB04794)
- Weight
- Average: 310.3917
Monoisotopic: 310.146998586 - Chemical Formula
- C22H18N2
- Synonyms
- (+-)-1-(p,alpha-Diphenylbenzyl)imidazole
- 1-((4-Biphenylyl)phenylmethyl)-1H-imidazole
- 1-(alpha-(4-Biphenylyl)benzyl)imidazole
- 1-(p,alpha-Diphenylbenzyl)imidazole
- 1-[biphenyl-4-yl(phenyl)methyl]imidazole
- Bifonazol
- Bifonazole
- Bifonazolum
- External IDs
- BAY H 4502
- BAY-H-4502
Pharmacology
- Indication
Used for the treatment of various topical fungal infections, including athlete's foot (tinea pedis).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Dermatomycoses •••••••••••• •••••••• ••••• •••••• •••• •••••••• Used in combination to treat Fungal infection of nail Combination Product in combination with: Urea (DB03904) ••• ••• •••••••• Treatment of Infections, fungal •••••••••••• ••••••••• ••••• Treatment of Infections, fungal of the skin folds •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Bifonazole is a type of antifungal medicine known as an imidazole. It kills fungi and yeasts by interfering with their cell membranes.
- Mechanism of action
Bifonazole works by inhibiting the production of a substance called ergosterol, which is an essential component of fungal cell membranes.It acts to destabilize the fungal cyctochrome p450 51 enzyme (also known as Lanosterol 14-alpha demethylase). This is vital in the cell membrance structure of the fungus. Its inhibition leads to cell lysis. The disruption in production of ergosterol disrupts the cell membrane and causes holes to appear. The cell membranes of fungi are vital for their survival. They keep unwanted substances from entering the cells and stop the contents of the cells from leaking out. As bifonazole causes holes to appear in the cell membranes, essential constituents of the fungal cells can leak out. This kills the fungi.
Target Actions Organism ACytochrome P450 51 inhibitorYeast UCytochrome P450 2B6 Not Available Humans - Absorption
Very low absorption following topical administration (0.6% of an applied dose). In cases of skin lesions absorption is increased (2.5%).
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
1-2 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The metabolism of Abemaciclib can be decreased when combined with Bifonazole. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Bifonazole. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Bifonazole. Acetaminophen Bifonazole may increase the hepatotoxic activities of Acetaminophen. Albendazole The metabolism of Albendazole can be decreased when combined with Bifonazole. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Amycor (Merck) / Azolmen (Menarini) / Bayclear Plus (Bayer) / Bifonol (Mayado Seiyaku) / Canespor (Bayer) / Canesten (Bayer) / Mycospor (Bayer)
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image CANESPRO ONCE DAILY CREAM 1% Cream 1 % Topical BAYER (SOUTH EAST ASIA) PTE LTD 2018-01-02 Not applicable Singapore 
คาเนสเทน โอ.ดี. Cream 1 %w/w Topical บริษัท ไบเออร์ไทย จำกัด 2011-05-20 Not applicable Thailand 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Canesten Bifonazol comp. - Salbe + Nagelset Bifonazole (0.01 g/g) + Urea (0.4 g/g) Ointment Topical Bayer Austria Ges.M.B.H. 1997-12-02 Not applicable Austria 
Categories
- ATC Codes
- D01AC10 — Bifonazole
- D01AC — Imidazole and triazole derivatives
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- Drug Categories
- Anti-Infective Agents
- Antifungal Agents
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Azole Antifungals
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Imidazole and Triazole Derivatives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Biphenyls and derivatives / N-substituted imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Azole / Biphenyl / Diphenylmethane / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / N-substituted imidazole / Organic nitrogen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- imidazoles, biphenyls (CHEBI:78692)
- Affected organisms
- Fungi
Chemical Identifiers
- UNII
- QYJ305Z91O
- CAS number
- 60628-96-8
- InChI Key
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N
- 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
- IUPAC Name
- 1-({[1,1'-biphenyl]-4-yl}(phenyl)methyl)-1H-imidazole
- SMILES
- C1=CN(C=N1)C(C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1
References
- Synthesis Reference
Regal, E., Draber, W., Buchel, K.H.and Plempel, M.; U.S. Patent 4,118,487; October 3,1978; assigned to Bayer A.G.
US4118487- General References
- Watanabe S, Takahashi H, Nishikawa T, Takiuchi I, Higashi N, Nishimoto K, Kagawa S, Yamaguchi H, Ogawa H: A comparative clinical study between 2 weeks of luliconazole 1% cream treatment and 4 weeks of bifonazole 1% cream treatment for tinea pedis. Mycoses. 2006 May;49(3):236-41. [Article]
- Cho KJ, Su W, Chen WC, Law YP, Fang HC, Liu CP, Cheng JS, Lee KC, Lo YK, Chang HT, Huang JK, Jan CR: Mechanism of bifonazole-induced [Ca2+]i increases in MDCK renal tubular cells. Chin J Physiol. 2001 Sep 30;44(3):97-101. [Article]
- Tanuma H, Doi M, Sato N, Nishiyama S, Abe M, Kume H, Katsuoka K: 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. Mycoses. 2000;43(3-4):129-37. [Article]
- Berg D, Regel E, Harenberg HE, Plempel M: Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole. Arzneimittelforschung. 1984;34(2):139-46. [Article]
- External Links
- Human Metabolome Database
- HMDB0015583
- PubChem Compound
- 2378
- PubChem Substance
- 46507284
- ChemSpider
- 2287
- BindingDB
- 50128548
- 19295
- ChEBI
- 78692
- ChEMBL
- CHEMBL277535
- Therapeutic Targets Database
- DAP000877
- PharmGKB
- PA164746464
- PDBe Ligand
- TMI
- Wikipedia
- Bifonazole
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Foot Dermatoses 1 3 Completed Treatment Onychomycosis 1 2 Completed Treatment Tinea Pedis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Lotion Topical Gel Topical 10 mg/g Solution Oral 10 mg/mL Spray Oral 10 mg/mL Cream Topical 10 MG/G Ointment Cutaneous 1.000 g Cream Topical 1 % w/w Cream Topical Ointment Topical Spray Oral 10 mg/g Aerosol, foam Topical Gel Topical Powder Topical Solution Topical Ointment Topical 1.00 g Ointment Topical 1 g Cream Topical 1 % Gel Topical 1 g Powder Topical 1 g Solution Topical 1 g Cream Cutaneous 1.000 g Ointment Topical 1.000 g Cream Topical 1 g Cream Topical 1 %w/w - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 142 Regal, E., Draber, W., Buchel, K.H.and Plempel, M.; U.S. Patent 4,118,487; October 3,1978; assigned to Bayer A.G. logP 4.77 BIOBYTE (1995) - Predicted Properties
Property Value Source Water Solubility 0.00245 mg/mL ALOGPS logP 4.92 ALOGPS logP 5.23 Chemaxon logS -5.1 ALOGPS pKa (Strongest Basic) 6.36 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 17.82 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 97.94 m3·mol-1 Chemaxon Polarizability 35.41 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9934 Blood Brain Barrier + 0.9828 Caco-2 permeable + 0.6357 P-glycoprotein substrate Non-substrate 0.7794 P-glycoprotein inhibitor I Non-inhibitor 0.8037 P-glycoprotein inhibitor II Non-inhibitor 0.8724 Renal organic cation transporter Non-inhibitor 0.6194 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Non-substrate 0.7693 CYP450 1A2 substrate Inhibitor 0.7884 CYP450 2C9 inhibitor Non-inhibitor 0.6395 CYP450 2D6 inhibitor Inhibitor 0.6381 CYP450 2C19 inhibitor Inhibitor 0.8503 CYP450 3A4 inhibitor Inhibitor 0.578 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9523 Ames test AMES toxic 0.5674 Carcinogenicity Non-carcinogens 0.9066 Biodegradation Not ready biodegradable 0.9521 Rat acute toxicity 2.3581 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.967 hERG inhibition (predictor II) Non-inhibitor 0.6458
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 193.904365 predictedDarkChem Lite v0.1.0 [M-H]- 172.70647 predictedDeepCCS 1.0 (2019) [M+H]+ 193.907465 predictedDarkChem Lite v0.1.0 [M+H]+ 175.06444 predictedDeepCCS 1.0 (2019) [M+Na]+ 193.812365 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.20006 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Yeast
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sterol 14-demethylase activity
- Specific Function
- Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
- Gene Name
- ERG11
- Uniprot ID
- P10613
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 60674.965 Da
References
- Carrillo-Munoz AJ, Giusiano G, Ezkurra PA, Quindos G: Antifungal agents: mode of action in yeast cells. Rev Esp Quimioter. 2006 Jun;19(2):130-9. [Article]
- Rossello A, Bertini S, Lapucci A, Macchia M, Martinelli A, Rapposelli S, Herreros E, Macchia B: Synthesis, antifungal activity, and molecular modeling studies of new inverted oxime ethers of oxiconazole. J Med Chem. 2002 Oct 24;45(22):4903-12. [Article]
- Berg D, Plempel M: Bifonazole, a biochemist's view. Dermatologica. 1984;169 Suppl 1:3-9. [Article]
- Berg D, Regel E, Harenberg HE, Plempel M: Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole. Arzneimittelforschung. 1984;34(2):139-46. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- Trosken ER, Scholz K, Lutz RW, Volkel W, Zarn JA, Lutz WK: Comparative assessment of the inhibition of recombinant human CYP19 (aromatase) by azoles used in agriculture and as drugs for humans. Endocr Res. 2004 Aug;30(3):387-94. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Tassaneeyakul W, Birkett DJ, Miners JO: Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica. 1998 Mar;28(3):293-301. doi: 10.1080/004982598239579 . [Article]
- Monostory K, Hazai E, Vereczkey L: Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40. doi: 10.1016/j.cbi.2004.03.003. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Monostory K, Hazai E, Vereczkey L: Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40. doi: 10.1016/j.cbi.2004.03.003. [Article]
Drug created at September 11, 2007 17:49 / Updated at June 12, 2021 10:53