<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2753</id>
  <title>T3D2711</title>
  <common-name>Fluconazole</common-name>
  <description>Fluconazole is only found in individuals that have used or taken this drug. It is a triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS. Fluconazole 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. Fluconazole 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>86386-73-4</cas>
  <pubchem-id>3365</pubchem-id>
  <chemical-formula>C13H12F2N6O</chemical-formula>
  <weight>306.104060</weight>
  <appearance>White powder.</appearance>
  <melting-point>138-140°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Intravenous, Oral</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Fluconazole 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. Fluconazole 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Route of Elimination: In normal volunteers, fluconazole is cleared primarily by renal excretion, with approximately 80% of the administered dose appearing in the urine as unchanged drug.Half Life: 30 hours (range 20-50 hours)</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of fungal infections.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Symptoms of overdose include hallucinations and paranoid behavior.</symptoms>
  <treatment>In the event of overdose, symptomatic treatment (with supportive measures and gastric lavage if clinically indicated) should be instituted. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:26:16Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:50Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Fluconazole</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>46081</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Fluconazole</stitch-id>
  <drugbank-id>DB00196</drugbank-id>
  <pdb-id>TPF</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>OC(CN1C=NC=N1)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1</moldb-smiles>
  <moldb-formula>C13H12F2N6O</moldb-formula>
  <moldb-inchi>InChI=1S/C13H12F2N6O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9,22H,4-5H2</moldb-inchi>
  <moldb-inchikey>InChIKey=RFHAOTPXVQNOHP-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">306.2708</moldb-average-mass>
  <moldb-mono-mass type="decimal">306.104065446</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.4</logp>
  <hmdb-id>HMDB14342</hmdb-id>
  <chembl-id>CHEMBL106</chembl-id>
  <chemspider-id>3248</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/Fluconazole.htm"&gt;DrugSyn.org&lt;/a&gt;&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
