Oxiconazole

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
Thumb
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.

Pharmacology
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Associated Conditions
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Contraindications
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Pharmacodynamics

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.

TargetActionsOrganism
ACytochrome P450 51
inhibitor
Yeast
ALanosterol synthase
inhibitor
Yeast
UNuclear receptor subfamily 1 group I member 2
partial agonist
Humans
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
Adverseeffects
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Toxicity

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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
CapmatinibThe serum concentration of Capmatinib can be decreased when it is combined with Oxiconazole.
ClindamycinThe metabolism of Clindamycin can be increased when combined with Oxiconazole.
LemborexantThe serum concentration of Lemborexant can be decreased when it is combined with Oxiconazole.
LumateperoneThe serum concentration of Lumateperone can be decreased when it is combined with Oxiconazole.
OliceridineThe serum concentration of Oliceridine can be decreased when it is combined with Oxiconazole.
RanolazineThe metabolism of Ranolazine can be increased when combined with Oxiconazole.
RimegepantThe metabolism of Rimegepant can be increased when combined with Oxiconazole.
Segesterone acetateThe metabolism of Segesterone acetate can be increased when combined with Oxiconazole.
SelpercatinibThe serum concentration of Selpercatinib can be decreased when it is combined with Oxiconazole.
TivozanibThe metabolism of Tivozanib can be increased when combined with Oxiconazole.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Oxiconazole nitrateRQ8UL4C17S64211-46-7WVNOAGNOIPTWPT-NDUABGMUSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OxistatCream10 mg/1gTopicalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2006-01-252012-10-25US flag
OxistatLotion30 mg/1gTopicalRebel Distributors2006-01-25Not applicableUS flag
OxistatCream10 mg/1gTopicalPharmaDerm a division of Fougera Pharmaceuticals Inc.1988-12-30Not applicableUS flag
OxistatCream10 mg/1gTopicalGlaxosmithkline Inc2006-02-022011-12-31US flag
OxistatLotion10 mg/1gTopicalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2006-01-252012-12-04US flag
OxistatLotion10 mg/1mLTopicalGlaxosmithkline Inc2006-02-022011-02-11US flag
OxistatLotion10 mg/1mLTopicalPharmaDerm a division of Fougera Pharmaceuticals Inc.1992-09-30Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Oxiconazole NitrateCream10 mg/1gTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2016-03-09Not applicableUS flag
Oxiconazole NitrateCream10 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2016-03-07Not applicableUS flag
Oxiconazole Nitrate Cream 1%Cream10 mg/1gTopicalWelgo, Llc2016-08-012017-12-31US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OxizoleCream1 %TopicalValeo Pharma Corp.1998-05-212006-07-31Canada flag
OxizoleLotion10 mg / gTopicalStiefel Laboratories, Inc.1998-05-212002-04-02Canada flag

Categories

ATC Codes
D01AC11 — OxiconazoleG01AF17 — OxiconazoleG01AF20 — Combinations of imidazole derivatives
Drug Categories
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
  1. 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]
  2. Fromtling RA: Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. [Article]
  3. FDA Approved Drug Products: OXISTAT (oxiconazole nitrate) topical [Link]
KEGG Drug
D08313
KEGG Compound
C08074
PubChem Compound
5353853
PubChem Substance
46504752
ChemSpider
4510239
BindingDB
50051844
RxNav
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
PhaseStatusPurposeConditionsCount
1CompletedTreatmentTinea infections1
1CompletedTreatmentTinea Pedis1

Pharmacoeconomics

Manufacturers
  • Altana inc
Packagers
  • Dispensing Solutions
  • GlaxoSmithKline Inc.
  • Nycomed Inc.
  • Pharmaderm
  • Rebel Distributors Corp.
Dosage Forms
FormRouteStrength
SprayTopical
CreamTopical
CreamTopical10 mg/1g
LotionTopical10 mg/1mL
LotionTopical10 mg/1g
LotionTopical30 mg/1g
CreamTopical1 %
LotionTopical10 mg / g
Prices
Unit descriptionCostUnit
Oxistat 1% Cream 60 gm Tube157.99USD tube
Oxistat 1% Lotion 30ml Bottle93.13USD bottle
Oxistat 1% Cream 30 gm Tube90.31USD tube
Oxistat 1% Cream 15 gm Tube48.99USD tube
Oxistat 1% cream2.23USD 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
PropertyValueSource
Water Solubility0.00191 mg/mLALOGPS
logP5.28ALOGPS
logP5.84ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)6.74ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.41 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.95 m3·mol-1ChemAxon
Polarizability40.79 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9903
Blood Brain Barrier+0.9699
Caco-2 permeable+0.5346
P-glycoprotein substrateNon-substrate0.6346
P-glycoprotein inhibitor INon-inhibitor0.7469
P-glycoprotein inhibitor IIInhibitor0.8492
Renal organic cation transporterInhibitor0.8361
CYP450 2C9 substrateNon-substrate0.8221
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6122
CYP450 1A2 substrateInhibitor0.793
CYP450 2C9 inhibitorInhibitor0.6532
CYP450 2D6 inhibitorNon-inhibitor0.6844
CYP450 2C19 inhibitorInhibitor0.8635
CYP450 3A4 inhibitorInhibitor0.6477
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8414
Ames testNon AMES toxic0.7381
CarcinogenicityNon-carcinogens0.7601
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5642 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6542
hERG inhibition (predictor II)Inhibitor0.507
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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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
  1. 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]
  2. 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
  1. 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
  1. 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
  1. 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
  1. 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 on June 13, 2005 13:24 / Updated on October 03, 2021 00:54