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Cisapride information


Cisapride
Clinical data
Trade namesPrepulsid, Propulsid
AHFS/Drugs.comFDA Professional Drug Information
MedlinePlusa694006
Pregnancy
category
  • AU: B1
Routes of
administration
By mouth (tablets), suspension
ATC code
  • A03FA02 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[1]
  • UK: POM (Prescription only)
  • US: Withdrawn
Pharmacokinetic data
Bioavailability30-40%
Protein binding97.5%
Metabolismliver CYP3A4, intestinal
Elimination half-life10 hours
Excretionkidney, bile duct
Identifiers
IUPAC name
  • (±)-cis-4-amino-5-chloro-N-(1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl)-2-methoxybenzamide
CAS Number
  • 81098-60-4 checkY
PubChem CID
  • 2769
IUPHAR/BPS
  • 240
DrugBank
  • DB00604 checkY
ChemSpider
  • 2667 checkY
UNII
  • UVL329170W
KEGG
  • D00274 checkY
ChEMBL
  • ChEMBL1729 ☒N
CompTox Dashboard (EPA)
  • DTXSID3022825 Edit this at Wikidata
ECHA InfoCard100.072.423 Edit this at Wikidata
Chemical and physical data
FormulaC23H29ClFN3O4
Molar mass465.95 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • Clc1cc(c(OC)cc1N)C(=O)NC3CCN(CCCOc2ccc(F)cc2)CC3OC
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) checkY
  • Key:DCSUBABJRXZOMT-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Cisapride is a gastroprokinetic agent, a drug that increases motility in the upper gastrointestinal tract. It acts directly as a serotonin 5-HT4 receptor agonist and indirectly as a parasympathomimetic. Stimulation of the serotonin receptors increases acetylcholine release in the enteric nervous system. It has been sold under the trade names Prepulsid (Janssen-Ortho) and Propulsid (in the United States). It was discovered by Janssen Pharmaceuticals in 1980. In many countries, it has been either withdrawn from the market or had its indications limited due to incidence of serious cardiac side-effects.[2] Propulsid was linked to children's deaths.[3]

The commercial preparations of this drug are the racemic mixture of both enantiomers of the compound. The (+) enantiomer itself has the major pharmacologic effects and does not induce many of the detrimental side-effects of the mixture.[4]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ "Propulsid To Go Off Market - Warning". MedicineNet. Retrieved 2021-12-25.
  3. ^ "PROPULSID: A Heartburn Drug, Now Linked to Children's Deaths". Los Angeles Times. 2000-12-20. Retrieved 2021-12-25.
  4. ^ US patent 5955478, Gray NM, Young JW, "Methods for treating gastrointestinal motility dysfunction using optically pre (+) cisapride", issued 1999-Sep-21 

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gastritis due to GERD—Triple combination therapy with lansoprazole + cisapride + sucralfate can significantly improve symptoms and quality of life and...

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drugs should not be taken with itraconazole: amiodarone (Cordarone); cisapride dofetilide nisoldipine alcohol pimozide quinidine lurasidone lovastatin...

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Diazepam

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phenobarbital. Nefazodone can cause increased blood levels of benzodiazepines. Cisapride may enhance the absorption, and therefore the sedative activity, of diazepam...

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