cisapride

Ligand id: 240

Name: cisapride

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 86.05
Molecular weight 465.18
XLogP 2.79
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1993))
Withdrawn drug? Yes
IUPAC Name
4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
International Nonproprietary Names
INN number INN
5338 cisapride
Synonyms
Prepulsid® | Propulsid®
Database Links
BindingDB Ligand 50005836
CAS Registry No. 81098-60-4 (source: Scifinder)
ChEBI CHEBI:151790
ChEMBL Ligand CHEMBL1729
DrugBank Ligand DB00604
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
Search UniChem for chemical match using the InChIKey DCSUBABJRXZOMT-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone DCSUBABJRXZOMT
Wikipedia Cisapride
Comments
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.