<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4771</id>
  <title>T3D4716</title>
  <common-name>Thiotepa</common-name>
  <description>N,N'N'-triethylenethiophosphoramide (ThioTEPA) is a cancer chemotherapeutic member of the alkylating agent group, now in use for over 50 years. It is a stable derivative of N,N',N''- triethylenephosphoramide (TEPA). It is mostly used to treat breast cancer, ovarian cancer and bladder cancer. It is also used as conditioning for Bone marrow transplantation. Its main toxicity is myelosuppression.</description>
  <cas>52-24-4</cas>
  <pubchem-id>5453</pubchem-id>
  <chemical-formula>C6H12N3PS</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>51.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1.9E+005 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>The alkyl group is attached to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. These drugs act nonspecifically.</mechanism-of-toxicity>
  <metabolism>Route of Elimination: Urinary excretion of 14C-labeled thiotepa and metabolites in a 34-year old patient with metastatic carcinoma of the cecum who received a dose of 0.3 mg/kg intravenously was 63%.Half Life: 1.5 to 4.1 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>1, carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>ThioTEPA is used a as conditioning treatment prior to allogeneic or autologous haematopoietic progenitor cell transplantation (HPCT) in haematological diseases in adult and paediatric patients. Also, when high dose chemotherapy with HPCT support it is appropriate for the treatment of solid tumours in adult and paediatric patients.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T02:06:13Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:56Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Thiotepa</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07641</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>128310</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB04572</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>S=P(N1CC1)(N1CC1)N1CC1</moldb-smiles>
  <moldb-formula>C6H12N3PS</moldb-formula>
  <moldb-inchi>InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2</moldb-inchi>
  <moldb-inchikey>InChIKey=FOCVUCIESVLUNU-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">189.218</moldb-average-mass>
  <moldb-mono-mass type="decimal">189.048954601</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.53</logp>
  <hmdb-id>HMDB15576</hmdb-id>
  <chembl-id>CHEMBL671</chembl-id>
  <chemspider-id>5254</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;John Kazan, &amp;#8220;Process for producing thiotepa.&amp;#8221; U.S. Patent US4918199, issued February, 1954.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
