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Identification
NameOxiconazole
Accession NumberDB00239  (APRD01154)
TypeSmall Molecule
GroupsApproved
Description

Oxiconazole nitrate (U.S.: Oxistat, Canada: Oxizole) is an antifungal medication typically administered in a cream or lotion to treat skin infections such as athlete’s foot, jock itch and ringworm. [Wikipedia]

Structure
Thumb
Synonyms
Oxiconazol
Oxiconazole
Oxiconazolum
External Identifiers
  • Ro 13-8996
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxiconazole Nitratecream10 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2016-03-09Not applicableUs
Oxistatcream10 mg/gtopicalPharma Derm, A Division Of Nycomed Us Inc.2006-01-25Not applicableUs
Oxistatlotion30 mg/gtopicalRebel Distributors Corp.2006-01-25Not applicableUs
Oxistatlotion10 mg/mLtopicalPharma Derm A Division Of Fougera Pharmaceuticals Inc.1992-09-30Not applicableUs
Oxistatcream10 mg/gtopicalPharma Derm A Division Of Fougera Pharmaceuticals Inc.1988-12-30Not applicableUs
Oxistatlotion10 mg/gtopicalPharma Derm, A Division Of Nycomed Us Inc.2006-01-25Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxiconazole Nitratecream10 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2016-03-07Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxizolecream1 %topicalValeo Pharma Inc1998-05-212006-07-31Canada
Oxizolelotion10 mgtopicalStiefel Canada Ulc1998-05-212002-04-02Canada
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Oxiconazole nitrate
64211-46-7
Thumb
  • InChI Key: WVNOAGNOIPTWPT-NDUABGMUSA-N
  • Monoisotopic Mass: 489.9769157
  • Average Mass: 492.13
DBSALT000892
Categories
UNIIC668Q9I33J
CAS number64211-45-6
WeightAverage: 429.12
Monoisotopic: 426.9812729
Chemical FormulaC18H13Cl4N3O
InChI KeyQRJJEGAJXVEBNE-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
SMILES
ClC1=CC(Cl)=C(CO\N=C(/CN2C=CN=C2)C2=CC=C(Cl)C=C2Cl)C=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Substituents
  • 1,3-dichlorobenzene
  • N-substituted imidazole
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Oxime ether
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor treatment of dermal fungal infection.
PharmacodynamicsOxiconazole 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 actionOxiconazole 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.
Related Articles
AbsorptionSystemic absorption of oxiconazole is low.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySide effects incliude pruritus, burning, irritation, erythema, stinging and allergic contact dermatitis and folliculitis, fissuring, maceration rash and nodules.
Affected organisms
  • Fungi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Altana inc
Packagers
Dosage forms
FormRouteStrength
Creamtopical10 mg/g
Lotiontopical10 mg/mL
Lotiontopical10 mg/g
Lotiontopical30 mg/g
Creamtopical1 %
Lotiontopical10 mg
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.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00191 mg/mLALOGPS
logP5.28ALOGPS
logS-5.3ALOGPS
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

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. [PubMed:18468760 ]
  2. Fromtling RA: Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. [PubMed:3069196 ]
External Links
ATC CodesD01AC11G01AF17
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (33.7 KB)
MSDSDownload (24.5 KB)
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

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
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. [PubMed:16964330 ]
  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. [PubMed:12383016 ]
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
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. [PubMed:8144423 ]

Enzymes

Kind
Protein
Organism
Human
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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. [PubMed:17998298 ]
Kind
Protein
Organism
Human
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
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. [PubMed:21177487 ]
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Drug created on June 13, 2005 07:24 / Updated on May 02, 2016 16:22