<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3017</id>
  <title>T3D2975</title>
  <common-name>Perhexiline</common-name>
  <description>Perhexiline is only found in individuals that have used or taken this drug. It is a coronary vasodilator used especially for angina of effort. It may cause neuropathy and hepatitis. [PubChem]Perhexiline binds to the mitochondrial enzyme carnitine palmitoyltransferase (CPT)-1 and CPT-2. It acts by shifting myocardial substrate utilisation from long chain fatty acids to carbohydrates through inhibition of CPT-1 and, to a lesser extent, CPT-2, resulting in increased glucose and lactate utilization. This results in increased ATP production for the same O2 consumption as before and consequently increases myocardial efficiency.</description>
  <cas>6621-47-2</cas>
  <pubchem-id>4746</pubchem-id>
  <chemical-formula>C19H35N</chemical-formula>
  <weight>277.276950</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>0.0608 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Well absorbed (&gt;80%) from the gastrointestinal tract following oral administration.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Perhexiline binds to the mitochondrial enzyme carnitine palmitoyltransferase (CPT)-1 and CPT-2. It acts by shifting myocardial substrate utilisation from long chain fatty acids to carbohydrates through inhibition of CPT-1 and, to a lesser extent, CPT-2, resulting in increased glucose and lactate utilization. This results in increased ATP production for the same O2 consumption as before and consequently increases myocardial efficiency.</mechanism-of-toxicity>
  <metabolism>The principal metabolites of perhexiline in man are monohydroxyperhexiline (which is excreted, in part, conjugated with glucuronic acid) and dihydroxyperhexiline that accounts for a relatively small proportion of the total metabolites. Two unidentified metabolites have also been found in the faeces. The pharmacological activity of the metabolites is not known. Hydroxylation of perhexiline is controlled by cytochrome P450 2D6 (CY P450 2D6).Half Life: Variable and non-linear. Some reports show a half-life of 2-6 days, others indicate it could be as high as 30 days.</metabolism>
  <toxicity>LD50: 2150 mg/kg (Oral, Rat) (A308)LD50: 2641 mg/kg (Oral, Mouse) (A308)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the management of severe angina pectoris.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Short term adverse effects include nausea, transient dizziness, hypoglycaemia in diabetic patients, and torsade de pointes (rare).</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:28:18Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:54Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Perhexiline</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>35553</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Perhexiline</stitch-id>
  <drugbank-id>DB01074</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>C(C(C1CCCCC1)C1CCCCC1)C1CCCCN1</moldb-smiles>
  <moldb-formula>C19H35N</moldb-formula>
  <moldb-inchi>InChI=1/C19H35N/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18/h16-20H,1-15H2</moldb-inchi>
  <moldb-inchikey>InChIKey=CYXKNKQEMFBLER-UHFFFAOYNA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">277.4879</moldb-average-mass>
  <moldb-mono-mass type="decimal">277.276950125</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>6.2</logp>
  <hmdb-id>HMDB15207</hmdb-id>
  <chembl-id>CHEMBL75880</chembl-id>
  <chemspider-id>4584</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;Stephen W. Horgan, Frank P. Palopoli, Edward J. Schwoegler, &amp;#8220;Process for preparing 2-(2,2-dicyclohexylethyl)piperidine.&amp;#8221; U.S. Patent US4069222, issued August, 1950.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
