<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3030</id>
  <title>T3D2988</title>
  <common-name>Miconazole</common-name>
  <description>Miconazole is only found in individuals that have used or taken this drug. It is an imidazole antifungal agent that is used topically and by intravenous infusion. [PubChem] Miconazole interacts with 14-&amp;alpha; demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.</description>
  <cas>22916-47-8</cas>
  <pubchem-id>4189</pubchem-id>
  <chemical-formula>C18H14Cl4N2O</chemical-formula>
  <weight>413.986020</weight>
  <appearance>White powder.</appearance>
  <melting-point>159-163°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1g/100mL (20°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Topical</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Miconazole interacts with 14-&amp;alpha; demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity>LD50: 3800 mg/kg (Oral, Mouse) (A308)LD50: 3 gm/kg (Oral, Rat) (A308)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For topical application in the treatment of tinea pedis (athlete&amp;rsquo;s foot), tinea cruris, and tinea corporis caused by &lt;i&gt;Trichophyton rubrum&lt;/i&gt;, &lt;i&gt;Trichophyton mentagrophytes&lt;/i&gt;, and &lt;i&gt;Epidermophyton floccosum&lt;/i&gt;, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Ingestion of the amounts of the components contained in a tube of cream are unlikely to produce overdosage and toxic effects.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:28:24Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:54Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Miconazole</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C08070</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>6923</chebi-id>
  <biocyc-id>CPD-4501</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Miconazole</stitch-id>
  <drugbank-id>DB01110</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(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1</moldb-smiles>
  <moldb-formula>C18H14Cl4N2O</moldb-formula>
  <moldb-inchi>InChI=1/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2</moldb-inchi>
  <moldb-inchikey>InChIKey=BYBLEWFAAKGYCD-UHFFFAOYNA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">416.129</moldb-average-mass>
  <moldb-mono-mass type="decimal">413.986023908</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>6.1</logp>
  <hmdb-id>HMDB15242</hmdb-id>
  <chembl-id>CHEMBL91</chembl-id>
  <chemspider-id>4044</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/Miconazole.htm"&gt;DrugSyn.org&lt;/a&gt;&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
