cisapride
4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
Molecular Identity
cisapride
4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
PubChem CID: 6917698
Cisapride is the amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere. It has a role as a serotonergic agonist, an anti-ulcer drug and a gastrointestinal drug. It is a member of benzamides, a member of piperidines, an aromatic ether, an organofluorine compound, a substituted aniline and a member of monochlorobenzenes.
2D Structure
Properties
C23H29ClFN3O4
Molecular Formula
465.90
Molecular Weight
g/mol
465.1831
Exact Mass
Da
3.4
XLogP
Drug-like (Lipinski: < 5)
86.1
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
7
H-Bond Acceptors
581
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
cisapride81098-60-4CisapridaCisapridumEnteroprideKinestasePridesiaPrepulsidR 51619CHEBI:3720UVL329170Wcis-4-Amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-o-anisamideDTXSID3022825R-51,6194-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
Data from PubChem (NCBI)
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