:Cinitapride

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451552541

| IUPAC_name = 4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide

| image = Cinitapride.svg

| width = 222

| image2 = 3D Cinitapride.png

| chirality = Racemic mixture

| drug_name =

| tradename = Cintapro, Pemix, Gapulsid

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 66564-14-5

| ATC_prefix = A03

| ATC_suffix = FA08

| PubChem = 68867

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB08810

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 62099

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104523

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = R8I97I2L24

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07700

| C=21 | H=30 | N=4 | O=4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C21H30N4O4/c1-2-29-20-13-18(22)19(25(27)28)12-17(20)21(26)23-16-8-10-24(11-9-16)14-15-6-4-3-5-7-15/h3-4,12-13,15-16H,2,5-11,14,22H2,1H3,(H,23,26)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ZDLBNXXKDMLZMF-UHFFFAOYSA-N

}}

Cinitapride (trade names Cintapro, Pemix, Gapulsid) is a gastroprokinetic agent and antiemetic agent of the benzamide class which is marketed in India, Mexico, Pakistan, Spain,{{cite journal | vauthors = Robert M, Salvà M, Segarra R | title = The prokinetic cinitapride has no clinically relevant pharmacokinetic interaction and effect on QT during coadministration with ketoconazole | journal = Drug Metabolism and Disposition | volume = 35 | issue = 7 | pages = 1149–56 |date=July 2007 | pmid = 17437965 | doi = 10.1124/dmd.106.010835 | s2cid = 1284844 | url = http://dmd.aspetjournals.org/cgi/pmidlookup?view=long&pmid=17437965|display-authors=etal| url-access = subscription }}{{cite journal | vauthors = Fernández AG, Massingham R | title = Peripheral receptor populations involved in the regulation of gastrointestinal motility and the pharmacological actions of metoclopramide-like drugs | journal = Life Sciences | volume = 36 | issue = 1 | pages = 1–14 |date=January 1985 | pmid = 2981378 | doi = 10.1016/0024-3205(85)90280-2}} Croatia and the Czech Republic. It acts as an agonist of the 5-HT1 and 5-HT4 receptors and as an antagonist of the 5-HT2 receptors.{{cite journal | vauthors = Alarcón-de-la-Lastra Romero C, López A, Martín MJ, la Casa C, Motilva V | title = Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds | journal = Pharmacology | volume = 54 | issue = 4 | pages = 193–202 |date=April 1997 | pmid = 9211565 | doi = 10.1159/000139487}}{{cite journal | vauthors = Alarcón de la Lastra C, La Casa C, Martin MJ, Motilva V | title = Effects of cinitapride on gastric ulceration and secretion in rats | journal = Inflammation Research | volume = 47 | issue = 3 | pages = 131–6 | date = March 1998 | pmid = 9562338 | doi = 10.1007/s000110050301 | s2cid = 25620004 | url = http://link.springer-ny.com/link/service/journals/00011/bibs/8047003/80470131.htm | access-date = 2010-02-27 | archive-url = https://web.archive.org/web/19990827033745/http://link.springer-ny.com/link/service/journals/00011/bibs/8047003/80470131.htm | archive-date = 1999-08-27 | url-status = dead | url-access = subscription }}

Uses

It is indicated for the treatment of gastrointestinal disorders associated with motility disturbances such as gastroesophageal reflux disease, non-ulcer dyspepsia and delayed gastric emptying. It may be also used in the management of nausea and vomiting. Cinitapride works by increasing the movement of esophagus, stomach, and intestines during digestion. It also increases the strength of muscle between esophagus and stomach to prevent reflux conditions.

Synthesis

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Cinitapride is the amide formed by reacting methyl 4-amino-2-ethoxy-5-nitrobenzoate (1) with the 4-aminopiperidine derivative (2).{{cite patent |country=GB |number=1574419 |title=Piperidine compounds |inventor=Inglesias, J.B; Soto, J.P; Noverola, A.V; Mauri, J.M |status=patent |gdate=1980-09-03 |fdate=1977-11-11 |pridate=1977-11-11 |assign1=Anphar SA }}{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-03-0165 |title=Cinitapride |publisher=Thieme |access-date=2024-07-02}}

References