<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4868</id>
  <title>T3D4813</title>
  <common-name>Masoprocol</common-name>
  <description>A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils. </description>
  <cas>500-38-9</cas>
  <pubchem-id>71398</pubchem-id>
  <chemical-formula>C18H22O4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>185.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility nil="true"/>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Less than 1%-2% is absorbed through the skin over a 4-day period following application.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Although the exact mechanism of action is not known, studies have shown that masoprocol is a potent 5-lipoxygenase inhibitor and has antiproliferative activity against keratinocytes in tissue culture, but the relationship between this activity and its effectiveness in actinic keratoses is unknown. Masoprocol also inhibits prostaglandins but the significance of this action is not yet known.</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Used for the treatment of actinic keratoses (precancerous skin growths that can become malignant if left untreated).</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Symptoms of overdose or allergic reaction include bluish coloration of skin, dizziness, severe, or feeling faint, wheezing or trouble in breathing.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T05:17:43Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:57Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Masoprocol</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C10719</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id>CPD-7661</biocyc-id>
  <ctd-id>D009637</ctd-id>
  <stitch-id nil="true"/>
  <drugbank-id>DB00179</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@](C)(CC1=CC(O)=C(O)C=C1)[C@]([H])(C)CC1=CC(O)=C(O)C=C1</moldb-smiles>
  <moldb-formula>C18H22O4</moldb-formula>
  <moldb-inchi>InChI=1/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3/t11-,12+</moldb-inchi>
  <moldb-inchikey>InChIKey=HCZKYJDFEPMADG-TXEJJXNPNA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">302.3649</moldb-average-mass>
  <moldb-mono-mass type="decimal">302.151809192</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>5.8</logp>
  <hmdb-id>HMDB12270</hmdb-id>
  <chembl-id>CHEMBL52</chembl-id>
  <chemspider-id>64490</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></synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
