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)
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Molecular structure representations generated using Open Babel