Editing Cisapride (section)

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 460039920
| IUPAC_name = (±)-''cis''-4-amino-5-chloro-''N''-(1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl)-2-methoxybenzamide
| image = Cisapride enantiomers labelled.svg
| image_class = skin-invert-image
| width = 350px
| image2 = Cisapride enantiomers ball-and-stick models from xtal 1997.png
| width2 = 350px
<!--Clinical data-->
| tradename =  Prepulsid, Propulsid
| Drugs.com = {{drugs.com|pro|propulsid}}
| MedlinePlus = a694006
| pregnancy_AU = B1
| pregnancy_category = 
| legal_AU = S4
| legal_BR = C1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_UK = POM
| legal_US_comment = Withdrawn
| legal_status = 
| routes_of_administration = [[Oral administration|By mouth]] (tablets), suspension
<!--Pharmacokinetic data-->
| bioavailability = 30-40%
| protein_bound = 97.5%
| metabolism = liver [[CYP3A4]], intestinal
| elimination_half-life = 10 hours
| excretion = kidney, bile duct
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 81098-60-4
| ATC_prefix = A03
| ATC_suffix = FA02
| ATC_supplemental =  
| PubChem = 2769
| IUPHAR_ligand = 240
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00604
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2667
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UVL329170W
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00274
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1729
<!--Chemical data-->
| C=23 | H=29 | Cl=1 | F=1 | N=3 | O=4
| smiles = Clc1cc(c(OC)cc1N)C(=O)NC3CCN(CCCOc2ccc(F)cc2)CC3OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DCSUBABJRXZOMT-UHFFFAOYSA-N
}}
'''Cisapride''' is a [[gastroprokinetic agent]], a [[pharmaceutical drug|drug]] that increases [[motility]] in the upper [[gastrointestinal tract]]. It acts directly as a [[serotonin]] [[5-HT4 receptor|5-HT<sub>4</sub> 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.<ref>{{Cite web|title=Propulsid To Go Off Market - Warning|url=https://www.medicinenet.com/propulsid_to_go_off_market_-_warning/views.htm|access-date=2021-12-25|website=MedicineNet|language=en}}</ref>  Propulsid was linked to children's deaths.<ref>{{Cite web|date=2000-12-20|title=PROPULSID: A Heartburn Drug, Now Linked to Children's Deaths|url=https://www.latimes.com/nation/la-122001propulsid-story.html|access-date=2021-12-25|website=Los Angeles Times|language=en-US}}</ref>

The commercial preparations of this drug are the [[racemic]] mixture of both [[enantiomer]]s of the compound. The (+) enantiomer itself<!-- what is the absolute configuration? --> has the major pharmacologic effects and does not induce many of the detrimental side-effects of the mixture.<ref>{{US patent reference |number = 5955478 |y=  1999 |m= Sep |d= 21 | inventor = Gray NM, Young JW |title= Methods for treating gastrointestinal motility dysfunction using optically pre (+) cisapride }}</ref>