Cisapride (CHEM002228)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (11)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:14 UTC
Update Date2026-05-14 16:43:45 UTC
Accession NumberCHEM002228
Identification
Common NameCisapride
ClassSmall Molecule
DescriptionIn many countries (including Canada) cisapride has been either withdrawn or has had its indications limited due to reports about long QT syndrome due to cisapride, which predisposes to arrhythmias.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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Anti-Ulcer Agent
  • Drug
  • Ester
  • Ether
  • Gastrointestinal Agent
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Organofluoride
  • Prokinetic Agent
  • Serotonin Agonist
  • Serotonin Receptor Agonist
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-CisaprideChEBI
4-Amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamideChEBI
4-Amino-5-chloro-N-{1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-methoxy-benzamideChEBI
cis-4-Amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-O-anisamideChEBI
cis-4-Amino-5-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamideChEBI
cis-4-Amino-5-chloro-N-{1-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-O-anisamideChEBI
CisapridaChEBI
CisapridumChEBI
PropulsidHMDB
Chemical FormulaC23H29ClFN3O4
Average Molecular Mass465.945 g/mol
Monoisotopic Mass465.183 g/mol
CAS Registry Number81098-60-4
IUPAC Name4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
Traditional Name(+-)-cisapride
SMILESCO[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC
InChI IdentifierInChI=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
InChI KeyDCSUBABJRXZOMT-IRLDBZIGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzamides
Alternative Parents
Substituents
  • Aminobenzamide
  • Halobenzoic acid or derivatives
  • 3-halobenzoic acid or derivatives
  • Aminophenyl ether
  • Methoxyaniline
  • Benzamide
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Aniline or substituted anilines
  • Benzoyl
  • Phenol ether
  • Alkyl aryl ether
  • Halobenzene
  • Fluorobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Piperidine
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Carboxamide group
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organofluoride
  • Organopnictogen compound
  • Organic oxide
  • Organochloride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point110°C
Boiling PointNot Available
Solubility2.71 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP2.95ALOGPS
logP2.49ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)8.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.05 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity122.93 m³·mol⁻¹ChemAxon
Polarizability49.11 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2922000000-0772f474daac82b426eeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-0980000000-a0df861122e90da3494bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0980000000-a0df861122e90da3494bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0159-0710900000-262b97df953edaab4cfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0111900000-61265dea2a01bd8e8378Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0943300000-cdcfabdf19797140d795Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9861100000-46b94051a1f1227c9363Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0400900000-c6cda5b55f88160e99deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0921500000-6011948830548e90b8dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-2910000000-5144f15cb7a70d64b8a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0001900000-8df7d19bd80f8e92fe73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0439600000-d40cbd486ff327890e07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ea-4902100000-c20a14020bf3f34d23ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0100900000-10eb08fa13f12fb9bc9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-5915600000-de23551ac41099e763f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0il0-9411000000-a20e7213ffcaf2d0f91fSpectrum
Toxicity Profile
Route of ExposureCisapride is rapidly absorbed after oral administration, with an absolute bioavailability of 35-40%.
Mechanism of ToxicityCisapride acts through the stimulation of the serotonin 5-HT4 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.
MetabolismHepatic. Extensively metabolized via cytochrome P450 3A4 enzyme. Half Life: 6-12 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsDiarrhea, upset stomach, stomach discomfort, vision changes, constipation.
TreatmentIn 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. (3)
Concentrations
Not Available
DrugBank IDDB00604
HMDB IDHMDB0014742
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCisapride
Chemspider ID5292927
ChEBI ID3720
PubChem Compound ID6917698
Kegg Compound IDC06910
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Alfons Gaston Maria De Knaep, Luc Jozef Raphael Moens, Max Rey, “Synthesis of cisapride.” U.S. Patent US6218542, issued January, 1988.

MSDSLink
General References
1. Pearce RE, Gotschall RR, Kearns GL, Leeder JS: Cytochrome P450 Involvement in the biotransformation of cisapride and racemic norcisapride in vitro: differential activity of individual human CYP3A isoforms. Drug Metab Dispos. 2001 Dec;29(12):1548-54.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10891117
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12190308
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19110341
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19663444
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1995885
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=2139471