Identification
- Summary
Oxiconazole is a topical antifungal used to treat a variety of dermatophyte infections.
- Brand Names
- Oxistat
- Generic Name
- Oxiconazole
- DrugBank Accession Number
- DB00239
- Background
Oxiconazole is an antifungal agent that is commonly found in topical formulations. It is marketed under the brand names Oxistat and Oxistat, and is used in the treatment of various skin infections such as athlete's foot, jock itch and ringworm.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Oxiconazole (DB00239)
- Weight
- Average: 429.12
Monoisotopic: 426.9812729 - Chemical Formula
- C18H13Cl4N3O
- Synonyms
- 2',4'-Dichloro-2-imidazol-1-ylacetophenone (Z)-[O-(2,4-dichlorobenzyl)oxime]
- Oxiconazol
- Oxiconazole
- Oxiconazolum
- External IDs
- Ro 13-8996
Pharmacology
- Indication
For treatment of dermal fungal infection.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Fungal skin infection •••••••••••• Treatment of Tinea corporis •••••••••••• Treatment of Tinea cruris •••••••••••• Treatment of Tinea pedis •••••••••••• Treatment of Tinea versicolor •••••••••••• - Contraindications & Blackbox Warnings
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Oxiconazole is a broad-spectrum imidazole derivative whose antifungal activity is derived primarily from the inhibition of ergosterol biosynthesis, which is critical for cellular membrane integrity. It has fungicidal or fungistatic activity in vitro against a number of pathogenic fungi including the following dermatophytes, and yeasts: T. rubrum, T. mentagrophytes, T. tonsurans, T. violaceum, E. floccosum, M. canis, M. audouini, M. gypseum, C. albicans, and M. furfur.
- Mechanism of action
Oxiconazole inhibits ergosterol biosynthesis, which is required for cytoplasmic membrane integrity of fungi. 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. Oxiconazole has also been shown in inhibit DNA synthesis and suppress intracellular concentrations of ATP. Like other imidazole antifungals, Oxiconazole can increase membrane permeability to zinc, augmenting its cytotoxicity.
Target Actions Organism ACytochrome P450 51 inhibitorYeast ALanosterol synthase inhibitorYeast UNuclear receptor subfamily 1 group I member 2 partial agonistHumans - Absorption
Systemic absorption of oxiconazole is low.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Side effects incliude pruritus, burning, irritation, erythema, stinging and allergic contact dermatitis and folliculitis, fissuring, maceration rash and nodules.
- 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 softwareCapmatinib The serum concentration of Capmatinib can be decreased when it is combined with Oxiconazole. Clindamycin The metabolism of Clindamycin can be increased when combined with Oxiconazole. Clozapine The serum concentration of Clozapine can be decreased when it is combined with Oxiconazole. Doxorubicin The serum concentration of Doxorubicin can be decreased when it is combined with Oxiconazole. Lemborexant The serum concentration of Lemborexant can be decreased when it is combined with Oxiconazole. - Food Interactions
- No interactions found.
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.- Product Ingredients
Ingredient UNII CAS InChI Key Oxiconazole nitrate RQ8UL4C17S 64211-46-7 WVNOAGNOIPTWPT-NDUABGMUSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxistat Lotion 10 mg/1mL Topical PharmaDerm a division of Fougera Pharmaceuticals Inc. 1992-09-30 Not applicable US 
Oxistat Cream 10 mg/1g Topical Pharma Derm, A Division Of Fougera Pharmaceuticals Inc. 2006-01-25 2012-10-25 US Oxistat Lotion 30 mg/1g Topical Rebel Distributors 2006-01-25 Not applicable US Oxistat Cream 10 mg/1g Topical PharmaDerm a division of Fougera Pharmaceuticals Inc. 1988-12-30 Not applicable US Oxistat Cream 10 mg/1g Topical Glaxosmithkline Inc 2006-02-02 2011-12-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxiconazole Nitrate Cream 10 mg/1g Topical E. Fougera & Co. a division of Fougera Pharmaceuticals Inc. 2016-03-09 Not applicable US Oxiconazole Nitrate Cream 10 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2016-03-07 Not applicable US Oxiconazole Nitrate Cream 1% Cream 10 mg/1g Topical Welgo, Llc 2016-08-01 2017-12-31 US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxizole Cream 1 % Topical Valeo Pharma Corp. 1998-05-21 2006-07-31 Canada 
Oxizole Lotion 10 mg / g Topical Stiefel Laboratories, Inc. 1998-05-21 2002-04-02 Canada
Categories
- ATC Codes
- D01AC11 — Oxiconazole
- D01AC — Imidazole and triazole derivatives
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Anti-Infective Agents
- Antifungal Agents
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Azole Antifungals
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Imidazole and Triazole Derivatives
- Imidazole Derivatives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Dichlorobenzenes
- Alternative Parents
- N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- 1,3-dichlorobenzene / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / N-substituted imidazole
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- conazole antifungal drug, imidazoles, imidazole antifungal drug, oxime O-ether, dichlorobenzene (CHEBI:7825)
- Affected organisms
- Fungi
Chemical Identifiers
- UNII
- C668Q9I33J
- CAS number
- 64211-45-6
- InChI Key
- QRJJEGAJXVEBNE-HKOYGPOVSA-N
- InChI
- InChI=1S/C18H13Cl4N3O/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22/h1-8,11H,9-10H2/b24-18+
- IUPAC Name
- (Z)-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene][(2,4-dichlorophenyl)methoxy]amine
- SMILES
- ClC1=CC(Cl)=C(CO\N=C(/CN2C=CN=C2)C2=CC=C(Cl)C=C2Cl)C=C1
References
- Synthesis Reference
- US4124767
- General References
- Matsui H, Sakanashi Y, Oyama TM, Oyama Y, Yokota S, Ishida S, Okano Y, Oyama TB, Nishimura Y: Imidazole antifungals, but not triazole antifungals, increase membrane Zn2+ permeability in rat thymocytes Possible contribution to their cytotoxicity. Toxicology. 2008 Jun 27;248(2-3):142-50. doi: 10.1016/j.tox.2008.03.022. Epub 2008 Apr 7. [Article]
- Fromtling RA: Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. [Article]
- FDA Approved Drug Products: OXISTAT (oxiconazole nitrate) topical [Link]
- External Links
- KEGG Drug
- D08313
- KEGG Compound
- C08074
- PubChem Compound
- 5353853
- PubChem Substance
- 46504752
- ChemSpider
- 4510239
- BindingDB
- 50051844
- 32638
- ChEBI
- 7825
- ChEMBL
- CHEMBL1262
- ZINC
- ZINC000003873295
- Therapeutic Targets Database
- DAP001204
- PharmGKB
- PA164754742
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Oxiconazole
- FDA label
- Download (33.7 KB)
- MSDS
- Download (24.5 KB)
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 1 Completed Treatment Tinea infections 1 1 Completed Treatment Tinea Pedis 1
Pharmacoeconomics
- Manufacturers
- Altana inc
- Packagers
- Dispensing Solutions
- GlaxoSmithKline Inc.
- Nycomed Inc.
- Pharmaderm
- Rebel Distributors Corp.
- Dosage Forms
Form Route Strength Cream Topical 1.000 mg Spray Topical 1 % Cream Topical 10 mg/1g Lotion Topical 10 mg/1mL Lotion Topical 10 mg/1g Lotion Topical 30 mg/1g Cream Topical 1 % Lotion Topical 10 mg / g - Prices
Unit description Cost Unit Oxistat 1% Cream 60 gm Tube 157.99USD tube Oxistat 1% Lotion 30ml Bottle 93.13USD bottle Oxistat 1% Cream 30 gm Tube 90.31USD tube Oxistat 1% Cream 15 gm Tube 48.99USD tube Oxistat 1% cream 2.23USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00191 mg/mL ALOGPS logP 5.28 ALOGPS logP 5.84 Chemaxon logS -5.4 ALOGPS pKa (Strongest Basic) 6.74 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 39.41 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 105.95 m3·mol-1 Chemaxon Polarizability 40.79 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9903 Blood Brain Barrier + 0.9699 Caco-2 permeable + 0.5346 P-glycoprotein substrate Non-substrate 0.6346 P-glycoprotein inhibitor I Non-inhibitor 0.7469 P-glycoprotein inhibitor II Inhibitor 0.8492 Renal organic cation transporter Inhibitor 0.8361 CYP450 2C9 substrate Non-substrate 0.8221 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6122 CYP450 1A2 substrate Inhibitor 0.793 CYP450 2C9 inhibitor Inhibitor 0.6532 CYP450 2D6 inhibitor Non-inhibitor 0.6844 CYP450 2C19 inhibitor Inhibitor 0.8635 CYP450 3A4 inhibitor Inhibitor 0.6477 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8414 Ames test Non AMES toxic 0.7381 Carcinogenicity Non-carcinogens 0.7601 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5642 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6542 hERG inhibition (predictor II) Inhibitor 0.507
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0bu3-5923000000-a7d62bf7e3c6df2ca64f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0001900000-90c48e7e411ea8e9e5b3 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0560-9520800000-ae82942dfd9000942515 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-1111900000-00139fc6e60f7c73abf5 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9100000000-b29501993164113ac90c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00xr-2911100000-dcc08a2fb32c3a36dca1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-87af7e16a152620eb5e2 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.36497 predictedDeepCCS 1.0 (2019) [M+H]+ 189.72299 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.20271 predictedDeepCCS 1.0 (2019)
Targets
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- 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]
- Kind
- Protein
- Organism
- Yeast
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Lanosterol synthase activity
- Specific Function
- Catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol nucleus.
- Gene Name
- ERG7
- Uniprot ID
- Q04782
- Uniprot Name
- Lanosterol synthase
- Molecular Weight
- 83713.975 Da
References
- Gebre-Hiwot A, Frommel D: The in-vitro anti-leishmanial activity of inhibitors of ergosterol biosynthesis. J Antimicrob Chemother. 1993 Dec;32(6):837-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Partial agonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Svecova L, Vrzal R, Burysek L, Anzenbacherova E, Cerveny L, Grim J, Trejtnar F, Kunes J, Pour M, Staud F, Anzenbacher P, Dvorak Z, Pavek P: Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug Metab Dispos. 2008 Feb;36(2):339-48. Epub 2007 Nov 12. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- 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
- Svecova L, Vrzal R, Burysek L, Anzenbacherova E, Cerveny L, Grim J, Trejtnar F, Kunes J, Pour M, Staud F, Anzenbacher P, Dvorak Z, Pavek P: Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug Metab Dispos. 2008 Feb;36(2):339-48. Epub 2007 Nov 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Mahajan MK, Uttamsingh V, Daniels JS, Gan LS, LeDuc BW, Williams DA: In vitro metabolism of oxymetazoline: evidence for bioactivation to a reactive metabolite. Drug Metab Dispos. 2011 Apr;39(4):693-702. doi: 10.1124/dmd.110.036004. Epub 2010 Dec 21. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:43