<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3519</id>
  <title>T3D3477</title>
  <common-name>Allopurinol</common-name>
  <description>Allopurinol is only found in individuals that have used or taken this drug. It is a xanthine oxidase inhibitor that decreases uric acid production. It also acts as an antimetabolite on some simpler organisms. [PubChem] Allopurinol and its active metabolite, oxypurinol, inhibits the enzyme xanthine oxidase, blocking the conversion of the oxypurines hypoxanthine and xanthine to uric acid. Elevated concentrations of oxypurine and oxypurine inhibition of xanthine oxidase through negative feedback results in a decrease in the concentrations of uric acid in the serum and urine. Allopurinol also facilitates the incorporation of hypoxanthine and xanthine into DNA and RNA, leading to a feedback inhibition of de novo purin synthesis and a decrease in serum uric acid concentrations as a result of an increase in nucleotide concentration.</description>
  <cas>315-30-0</cas>
  <pubchem-id>2094</pubchem-id>
  <chemical-formula>C5H4N4O</chemical-formula>
  <weight>136.038510</weight>
  <appearance>White powder.</appearance>
  <melting-point>350°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>569 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Approximately 80-90% absorbed from the gastrointestinal tract.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Allopurinol inhibits the enzyme xanthine oxidase, blocking the conversion of the oxypurines hypoxanthine and xanthine to uric acid. Elevated concentrations of oxypurine and oxypurine inhibition of xanthine oxidase through negative feedback results in a decrease in the concentrations of uric acid in the blood and urine. Allopurinol also facilitates the incorporation of hypoxanthine and xanthine into DNA and RNA, resulting in further reductions of serum uric acid concentrations.</mechanism-of-toxicity>
  <metabolism>HepaticRoute of Elimination: Approximately  20% of the ingested allopurinol is excreted in the feces.Half Life: 1-3 hours</metabolism>
  <toxicity>LD&lt;sub&gt;50&lt;/sub&gt;=214 mg/kg (in mice)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of hyperuricemia associated with primary or secondary gout. Also indicated for the treatment of primary or secondary uric acid nephropathy, with or without the symptoms of gout, as well as chemotherapy-induced hyperuricemia and recurrent renal calculi.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>LD&lt;sub&gt;50&lt;/sub&gt;=214 mg/kg (in mice)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-30T17:58:37Z</created-at>
  <updated-at type="dateTime">2026-03-26T18:39:00Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Allopurinol</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>40279</chebi-id>
  <biocyc-id>CPD-9024</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Allopurinol  </stitch-id>
  <drugbank-id>DB00437</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>O=C1N=CN=C2NNC=C12</moldb-smiles>
  <moldb-formula>C5H4N4O</moldb-formula>
  <moldb-inchi>InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)</moldb-inchi>
  <moldb-inchikey>OFCNXPDARWKPPY-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">136.1115</moldb-average-mass>
  <moldb-mono-mass type="decimal">136.03851077</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-0.55</logp>
  <hmdb-id>HMDB14581</hmdb-id>
  <chembl-id>CHEMBL1467</chembl-id>
  <chemspider-id>2010</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;Druey, J. and Schmidt, P.; US. Patent 2868,803; January 13,1959; assigned to Ciba Pharmaceutical Products Inc.&lt;br /&gt;
Hitchings, G.H. and Falco, EA.; U.S. Patent 3,474,098; October 21,1969; assigned to Bur-&lt;br /&gt;
roughs Wellcome &amp;amp; Co.&lt;br /&gt;
Cresswell, R.M.and Mentha, J.W.; US.Patent4,146,713; March27,1979; assigned to Bur-&lt;br /&gt;
roughs Wellcome &amp;amp; Co.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002503</chemdb-id>
  <dsstox-id>DTXSID4022573</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00000618</susdat-id>
  <iupac>1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one</iupac>
</compound>
