<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4258</id>
  <title>T3D4204</title>
  <common-name>Mechlorethamine</common-name>
  <description>Mechlorethamine is only found in individuals that have used or taken this drug. It is a vesicant and necrotizing irritant destructive to mucous membranes. It was formerly used as a war gas. The hydrochloride is used as an antineoplastic in Hodgkin's disease and lymphomas. It causes severe gastrointestinal and bone marrow damage. Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations. Mechlorethamine is cell cycle phase-nonspecific.</description>
  <cas>51-75-2</cas>
  <pubchem-id>4033</pubchem-id>
  <chemical-formula>C5H11Cl2N</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>108 - 110°C</melting-point>
  <boiling-point>87°C at 1.80E+01 mm Hg</boiling-point>
  <density nil="true"/>
  <solubility>Very soluble</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Partially absorbed following intracavitary administration, most likely due to rapid deactivation by body fluids. When it is topically administered, systemic exposure was undetectable. </route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations. Mechlorethamine is cell cycle phase-nonspecific.</mechanism-of-toxicity>
  <metabolism>Undergoes rapid chemical transformation and combines with water or reactive compounds of cells, so that the drug is no longer present in active form a few minutes after administration.Half Life: 15 minutes</metabolism>
  <toxicity>The oral LD50 for a rat is 10 mg/kg. </toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>Chlormethine is probably carcinogenic to humans (Group 2A). Chlormethine is part of MOPP, a combination chemotherapy regimen that is carcinogenic to humans (Group 1). (L135)</carcinogenicity>
  <use-source>For the palliative treatment of Hodgkin's disease (Stages III and IV), lymphosarcoma, chronic myelocytic or chronic lymphocytic leukemia, polycythemia vera, mycosis fungoides, and bronchogenic carcinoma. Also for the palliative treatment of metastatic carcinoma resulting in effusion.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T05:52:43Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:42Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Mechlorethamine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07115</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>28925</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00888</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>CN(CCCl)CCCl</moldb-smiles>
  <moldb-formula>C5H11Cl2N</moldb-formula>
  <moldb-inchi>InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3</moldb-inchi>
  <moldb-inchikey>InChIKey=HAWPXGHAZFHHAD-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">156.054</moldb-average-mass>
  <moldb-mono-mass type="decimal">155.026854771</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.91</logp>
  <hmdb-id>HMDB15025</hmdb-id>
  <chembl-id>CHEMBL427</chembl-id>
  <chemspider-id>3893</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;Paul Siedlecki, &amp;#8220;Preparation of nitrogen mustard derivatives.&amp;#8221; U.S. Patent US20030162990, issued August 28, 2003.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
