<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2878</id>
  <title>T3D2836</title>
  <common-name>Cisapride</common-name>
  <description>In many countries (including Canada) cisapride has been either withdrawn or has had its indications limited due to reports about long QT syndrome due to cisapride, which predisposes to arrhythmias. The FDA issued a warning letter regarding this risk to health care professionals and patients.</description>
  <cas>81098-60-4</cas>
  <pubchem-id>6917698</pubchem-id>
  <chemical-formula>C23H29ClFN3O4</chemical-formula>
  <weight>465.183060</weight>
  <appearance>White powder.</appearance>
  <melting-point>110°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>2.71 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Cisapride is rapidly absorbed after oral administration, with an absolute bioavailability of 35-40%.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Cisapride acts through the stimulation of the serotonin 5-HT&lt;sub&gt;4&lt;/sub&gt; receptors which increases acetylcholine release in the enteric nervous system (specifically the myenteric plexus). This results in increased tone and amplitude of gastric (especially antral) contractions, relaxation of the pyloric sphincter and the duodenal bulb, and increased peristalsis of the duodenum and jejunum resulting in accelerated gastric emptying and intestinal transit.</mechanism-of-toxicity>
  <metabolism>Hepatic. Extensively metabolized via cytochrome P450 3A4 enzyme.Half Life: 6-12 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Diarrhea, upset stomach, stomach discomfort, vision changes, constipation.</symptoms>
  <treatment>In instances of overdose, patients should be evaluated for possible QT prolongation and ventricular arrhythmias, including torsades de pointes. Treatment should include gastric lavage and/or activated charcoal, close observation and general supportive measures. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:27:14Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:52Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Cisapride</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C06910</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>3720</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Cisapride</stitch-id>
  <drugbank-id>DB00604</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>[H][C@@]1(CN(CCCOC2=CC=C(F)C=C2)CC[C@@]1([H])N=C(O)C1=C(OC)C=C(N)C(Cl)=C1)OC</moldb-smiles>
  <moldb-formula>C23H29ClFN3O4</moldb-formula>
  <moldb-inchi>InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22+/m1/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=DCSUBABJRXZOMT-IRLDBZIGSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">465.945</moldb-average-mass>
  <moldb-mono-mass type="decimal">465.183062343</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>3.3</logp>
  <hmdb-id>HMDB14742</hmdb-id>
  <chembl-id>CHEMBL1729</chembl-id>
  <chemspider-id>5292927</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;Alfons Gaston Maria De Knaep, Luc Jozef Raphael Moens, Max Rey, &amp;#8220;Synthesis of cisapride.&amp;#8221; U.S. Patent US6218542, issued January, 1988.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
