<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4766</id>
  <title>T3D4711</title>
  <common-name>Procarbazine</common-name>
  <description>Procarbazine is only found in individuals that have used or taken this drug. It is an antineoplastic agent used primarily in combination with mechlorethamine, vincristine, and prednisone (the MOPP protocol) in the treatment of Hodgkin's disease. The precise mode of cytotoxic action of procarbazine has not been clearly defined. There is evidence that the drug may act by inhibition of protein, RNA and DNA synthesis. Studies have suggested that procarbazine may inhibit transmethylation of methyl groups of methionine into t-RNA. The absence of functional t-RNA could cause the cessation of protein synthesis and consequently DNA and RNA synthesis. In addition, procarbazine may directly damage DNA. Hydrogen peroxide, formed during the auto-oxidation of the drug, may attack protein sulfhydryl groups contained in residual protein which is tightly bound to DNA.</description>
  <cas>671-16-9</cas>
  <pubchem-id>4915</pubchem-id>
  <chemical-formula>C12H19N3O</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>223°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1420 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Procarbazine is rapidly and completely absorbed.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>The precise mode of cytotoxic action of procarbazine has not been clearly defined. There is evidence that the drug may act by inhibition of protein, RNA and DNA synthesis. Studies have suggested that procarbazine may inhibit transmethylation of methyl groups of methionine into t-RNA. The absence of functional t-RNA could cause the cessation of protein synthesis and consequently DNA and RNA synthesis. In addition, procarbazine may directly damage DNA. Hydrogen peroxide, formed during the auto-oxidation of the drug, may attack protein sulfhydryl groups contained in residual protein which is tightly bound to DNA.</mechanism-of-toxicity>
  <metabolism>Procarbazine is metabolized primarily in the liver and kidneys. The drug appears to be auto-oxidized to the azo derivative with the release of hydrogen peroxide. The azo derivative isomerizes to the hydrazone, and following hydrolysis splits into a benzylaldehyde derivative and methylhydrazine. The methylhydrazine is further degraded to CO&lt;sub&gt;2&lt;/sub&gt; and CH&lt;sub&gt;4&lt;/sub&gt; and possibly hydrazine, whereas the aldehyde is oxidized to N-isopropylterephthalamic acid, which is excreted in the urine.Half Life: 10 minutes</metabolism>
  <toxicity>LD&lt;sub&gt;50&lt;/sub&gt;=785 mg/kg (orally in rats)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>Procarbazine is part of MOPP, a combination chemotherapy regimen that is carcinogenic to humans (Group 1). (L135)</carcinogenicity>
  <use-source>For use with other anticancer drugs for the treatment of stage III and stage IV Hodgkin's disease.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T02:06:00Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:55Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Procarbazine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07402</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>366225</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB01168</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>CNNCC1=CC=C(C=C1)C(=O)NC(C)C</moldb-smiles>
  <moldb-formula>C12H19N3O</moldb-formula>
  <moldb-inchi>InChI=1S/C12H19N3O/c1-9(2)15-12(16)11-6-4-10(5-7-11)8-14-13-3/h4-7,9,13-14H,8H2,1-3H3,(H,15,16)</moldb-inchi>
  <moldb-inchikey>InChIKey=CPTBDICYNRMXFX-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">221.2988</moldb-average-mass>
  <moldb-mono-mass type="decimal">221.152812245</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.06</logp>
  <hmdb-id>HMDB15299</hmdb-id>
  <chembl-id>CHEMBL1321</chembl-id>
  <chemspider-id>4746</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/Procarbazine.htm"&gt;DrugSyn.org&lt;/a&gt;&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
