<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2764</id>
  <title>T3D2722</title>
  <common-name>Oxiconazole</common-name>
  <description>Oxiconazole 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. 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.</description>
  <cas>64211-46-7</cas>
  <pubchem-id>5361463</pubchem-id>
  <chemical-formula>C18H13Cl4N3O</chemical-formula>
  <weight>426.981270</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1.91e-03 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Topical; systemic absorption of oxiconazole is low.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>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.</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For treatment of dermal fungal infection.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Side effects incliude pruritus, burning, irritation, erythema, stinging and allergic contact dermatitis and folliculitis, fissuring, maceration rash and nodules.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:26:22Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:50Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Oxiconazole</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C08075</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Oxiconazole</stitch-id>
  <drugbank-id>DB00239</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>ClC1=CC(Cl)=C(CO\N=C(\CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1</moldb-smiles>
  <moldb-formula>C18H13Cl4N3O</moldb-formula>
  <moldb-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-</moldb-inchi>
  <moldb-inchikey>InChIKey=QRJJEGAJXVEBNE-MOHJPFBDSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">429.127</moldb-average-mass>
  <moldb-mono-mass type="decimal">426.981272881</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB14384</hmdb-id>
  <chembl-id>CHEMBL1262</chembl-id>
  <chemspider-id>4514745</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;&lt;a href="http://www.drugsyn.org/Oxiconazole.htm"&gt;DrugSyn.org&lt;/a&gt;&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
