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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1729
CHEMBL1729
Compound Name CISAPRIDE
ChEMBL Synonyms ALIMIX | PREPULSID QUICKLET | PROPULSID QUICKSOLV | Propulsid | CISAPRIDE | PREPULSID | R-51,619 | CISAPRIDE MONOHYDRATE | PROPULSID
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names PREPULSID | PROPULSID QUICKSOLV | ALIMIX | PREPULSID QUICKLET | PROPULSID
Molecular Formula C23H29ClFN3O4

Additional synonyms for CHEMBL1729 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COC1CN(CCCOc2ccc(F)cc2)CCC1NC(=O)c3cc(Cl)c(N)cc3OC
Standard InChI InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(2 ...
Download InChI
Standard InChI Key DCSUBABJRXZOMT-UHFFFAOYSA-N

Sources

  • BindingDB Database
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL1729

Molecule Features

CHEMBL1729 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 2000
Country United States
Reason Fatal arrhythmia
Class Cardiotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Serotonin 4 (5-HT4) receptor agonist Serotonin 4 (5-HT4) receptor DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Digestive System DiseasesD004066EFO:0000405digestive system disease4ATC

Clinical Data

ClinicalTrials.gov CISAPRIDE
The Cochrane Collaboration CISAPRIDE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1729. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1875 Serotonin 4 (5-HT4) receptor Homo sapiens 1.000
CHEMBL4317 Serotonin 4 (5-HT4) receptor Rattus norvegicus 1.000
CHEMBL5017 Serotonin 4 (5-HT4) receptor Cavia porcellus 1.000
CHEMBL339 Dopamine D2 receptor Rattus norvegicus 1.000
CHEMBL2411 Serotonin 3a (5-HT3a) receptor Rattus norvegicus 1.000
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.933
CHEMBL240 HERG Homo sapiens 0.895
CHEMBL1899 Serotonin 3a (5-HT3a) receptor Homo sapiens 0.679
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 0.441
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.262
CHEMBL219 Dopamine D4 receptor Homo sapiens 0.255



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1875 Serotonin 4 (5-HT4) receptor Homo sapiens 1.000
CHEMBL4317 Serotonin 4 (5-HT4) receptor Rattus norvegicus 1.000
CHEMBL5017 Serotonin 4 (5-HT4) receptor Cavia porcellus 1.000
CHEMBL2411 Serotonin 3a (5-HT3a) receptor Rattus norvegicus 1.000
CHEMBL339 Dopamine D2 receptor Rattus norvegicus 1.000
CHEMBL1899 Serotonin 3a (5-HT3a) receptor Homo sapiens 1.000
CHEMBL240 HERG Homo sapiens 1.000
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.960
CHEMBL234 Dopamine D3 receptor Homo sapiens 0.724
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 0.598
CHEMBL3138 Dopamine D3 receptor Rattus norvegicus 0.430
CHEMBL224 Serotonin 2a (5-HT2a) receptor Homo sapiens 0.398
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 0.360
CHEMBL219 Dopamine D4 receptor Homo sapiens 0.249

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
466 465.1831 3.36 9 86.05 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 2 0 7 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.01 7.47 2.83 2.46 2 32 0.44

Structural Alerts

There are 4 structural alerts for CHEMBL1729. To view alerts please click here.

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A03 - DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
A03F - PROPULSIVES
A03FA - Propulsives
A03FA02 - cisapride

ChemSpider ChemSpider:DCSUBABJRXZOMT-UHFFFAOYSA-N
PubChem SID: 144204250 SID: 170465200
Wikipedia Cisapride

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1729



ACToR 81098-60-4
BindingDB 50005836
ChEBI 95129
DrugCentral 660
eMolecules 31796143
EPA CompTox Dashboard DTXSID3022825
Guide to Pharmacology 240
IBM Patent System 4900842F5B7D44BDF2662C2B0010B3A6
KEGG Ligand C06910
LINCS LSM-6397
Mcule MCULE-7144129340
MolPort MolPort-003-666-853
Nikkaji J1.137.153A
PharmGKB PA449011
PubChem 2769
PubChem: Thomson Pharma 14882747
SureChEMBL SCHEMBL16131

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/DCSUBABJRXZOMT-UHFFFAOYSA-N spacer
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