cisapride   Click here for help

GtoPdb Ligand ID: 240

Synonyms: Prepulsid® | Propulsid®
Approved drug
cisapride is an approved drug (FDA (1993))
Compound class: Synthetic organic
Comment: Cisapride is an enantioneric mixture and we show the non-stereoisomeric structure here to represent the mixture. One stereoisomeric structure is shown by CHEMBL560739.
Cisapride must be used with caution due to reports of drug-induced arrhythmias and long QT syndrome. Although this drug was originally given marketing approval by the US FDA in 1993, all registered formulations have since been discontinued. In the EU (since 2002) conditions of use have been applied to active marketing authorisations for cisapride containing medicinal products.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 86.05
Molecular weight 465.18
XLogP 3.28
No. Lipinski's rules broken 0
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Canonical SMILES COC1CN(CCCOc2ccc(cc2)F)CCC1NC(=O)c1cc(Cl)c(cc1OC)N
Isomeric SMILES COC1CN(CCCOc2ccc(cc2)F)CCC1NC(=O)c1cc(Cl)c(cc1OC)N
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)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1993))
Withdrawn drug? Yes
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
5338 cisapride
Synonyms Click here for help
Prepulsid® | Propulsid®
Database Links Click here for help
Specialist databases
GPCRdb Ligand cisapride
Other databases
BindingDB Ligand 50005836
CAS Registry No. 81098-60-4 (source: Scifinder)
ChEBI CHEBI:151790
ChEMBL Ligand CHEMBL1729
DrugBank Ligand DB00604
DrugCentral Ligand 660
GtoPdb PubChem SID 135650104
PubChem CID 2769
Search Google for chemical match using the InChIKey DCSUBABJRXZOMT-UHFFFAOYSA-N
Search Google for chemicals with the same backbone DCSUBABJRXZOMT
Search PubMed clinical trials cisapride
Search PubMed titles cisapride
Search PubMed titles/abstracts cisapride
UniChem Compound Search for chemical match using the InChIKey DCSUBABJRXZOMT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey DCSUBABJRXZOMT-UHFFFAOYSA-N
Wikipedia Cisapride