<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3034</id>
  <title>T3D2992</title>
  <common-name>Econazole</common-name>
  <description>Econazole is only found in individuals that have used or taken this drug. It is a broad spectrum antimycotic with some action against Gram positive bacteria. It is used topically in dermatomycoses also orally and parenterally. [PubChem] Econazole interacts with 14-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. Econazole 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>27220-47-9</cas>
  <pubchem-id>3198</pubchem-id>
  <chemical-formula>C18H15Cl3N2O</chemical-formula>
  <weight>380.025000</weight>
  <appearance>White powder.</appearance>
  <melting-point>162°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1.48e-03 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>After topical application to the skin of normal subjects, systemic absorption of econazole nitrate is extremely low. Although most of the applied drug remains on the skin surface, drug concentrations were found in the stratum corneum which, by far, exceeded the minimum inhibitory concentration for dermatophytes.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Econazole 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. Econazole 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>Hepatic.</metabolism>
  <toxicity>LD50: 462 mg/kg (Oral, Mouse) (A308)LD50: 462 mg/kg (Oral, Rat) (A308)LD50: 668 mg/kg (Oral, Guinea pig) (A308)LD50: &gt;160 mg/kg (Oral, Dog) (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, tinea cruris, and tinea corporis caused by &lt;i&gt;Trichophyton rubrum&lt;/i&gt;, &lt;i&gt;Trichophyton mentagrophytes&lt;/i&gt;, &lt;i&gt;Trichophyton tonsurans&lt;/i&gt;, &lt;i&gt;Microsporum canis&lt;/i&gt;, &lt;i&gt;Microsporum audouini&lt;/i&gt;, &lt;i&gt;Microsporum gypseum&lt;/i&gt;, and &lt;i&gt;Epidermophyton floccosum&lt;/i&gt;, in the treatment of cutaneous candidiasis, and in the treatment of tinea versicolor.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms></symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:28:25Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:55Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Econazole</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C08068</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>4754</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Econazole</stitch-id>
  <drugbank-id>DB01127</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=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1</moldb-smiles>
  <moldb-formula>C18H15Cl3N2O</moldb-formula>
  <moldb-inchi>InChI=1/C18H15Cl3N2O/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18H,10-11H2</moldb-inchi>
  <moldb-inchikey>InChIKey=LEZWWPYKPKIXLL-UHFFFAOYNA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">381.684</moldb-average-mass>
  <moldb-mono-mass type="decimal">380.024996233</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>5.5</logp>
  <hmdb-id>HMDB15259</hmdb-id>
  <chembl-id>CHEMBL808</chembl-id>
  <chemspider-id>3086</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;Godefroi, E.F. and Heeres, J.; U.S. Patent 3,717,655; February 20,1973; assigned to Jansen Pharmaceutica NV, Belgium.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
