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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:33 UTC
HMDB IDHMDB0014384
Secondary Accession Numbers
  • HMDB14384
Metabolite Identification
Common NameOxiconazole
DescriptionOxiconazole is only found in individuals that have used or taken this drug. It 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 ]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.
Structure
Data?1582753173
Synonyms
ValueSource
Oxiconazole nitrateHMDB
Chemical FormulaC18H13Cl4N3O
Average Molecular Weight429.127
Monoisotopic Molecular Weight426.981272881
IUPAC Name(E)-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene][(2,4-dichlorophenyl)methoxy]amine
Traditional Nameoxiconazole
CAS Registry Number64211-46-7
SMILES
ClC1=CC(Cl)=C(CO\N=C(\CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1
InChI Identifier
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-
InChI KeyQRJJEGAJXVEBNE-MOHJPFBDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes 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
  • Aryl chloride
  • Aryl halide
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0019 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP10(5.28) g/LALOGPS
logP10(5.84) g/LChemAxon
logS10(-5.4) g/LALOGPS
pKa (Strongest Basic)6.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.41 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.95 m³·mol⁻¹ChemAxon
Polarizability40.01 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxiconazoleClC1=CC(Cl)=C(CO\N=C(\CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C14276.5Standard polar33892256
OxiconazoleClC1=CC(Cl)=C(CO\N=C(\CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C13000.8Standard non polar33892256
OxiconazoleClC1=CC(Cl)=C(CO\N=C(\CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C13048.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxiconazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9615000000-f8d5fa55f90a3c0274d32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxiconazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxiconazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 10V, Positive-QTOFsplash10-004i-0040900000-2244e5a8bc8f622118d52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 20V, Positive-QTOFsplash10-000i-0390400000-e9f8c81da4249531df532016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 40V, Positive-QTOFsplash10-00xr-3920000000-2b8888d5586d800c98d92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 10V, Negative-QTOFsplash10-004i-0000900000-7ac95b33d5747267c8a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 20V, Negative-QTOFsplash10-0kdi-2691800000-c74d8b876a02007abf052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 40V, Negative-QTOFsplash10-060u-4930000000-773675c2f231353648b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 10V, Negative-QTOFsplash10-0059-5010900000-d5310ae0910fe9a240a52021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 20V, Negative-QTOFsplash10-001i-9020000000-a94bd8e0395e9db7e52a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 40V, Negative-QTOFsplash10-014i-9000000000-272c746157cbf85703452021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 10V, Positive-QTOFsplash10-004i-0000900000-4d57962ed63ea0d13a112021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 20V, Positive-QTOFsplash10-004i-0220900000-223705cb6ad47e786d5e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxiconazole 40V, Positive-QTOFsplash10-0aor-4931000000-07805722b64eb11345572021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00239 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00239 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4514745
KEGG Compound IDC08075
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxiconazole
METLIN IDNot Available
PubChem Compound5361463
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fromtling RA: Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. [PubMed:3069196 ]
  2. 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 ]

Enzymes

General function:
Involved in monooxygenase 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 xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 ]
General function:
Involved in monooxygenase 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:
55944.565
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 ]