Cinitapride

Cinitapride (trade names Cintapro, Pemix) is a gastroprokinetic agent and antiemetic agent of the benzamide class which is marketed in India, Mexico, Pakistan and Spain.^[1][2] It acts as an agonist of the 5-HT₁ and 5-HT₄ receptors and as an antagonist of the 5-HT₂ receptors.^[3][4]

Cinitapride

Clinical data
Trade names	Cintapro, Pemix
Routes of administration	Oral
ATC code	A03FA08 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide
CAS Number	66564-14-5 Y
PubChem CID	68867
DrugBank	DB08810 Y
ChemSpider	62099 Y
UNII	R8I97I2L24
KEGG	D07700 Y
ChEMBL	ChEMBL2104523 N
CompTox Dashboard (EPA)	DTXSID60867232
Chemical and physical data
Formula	C21H30N4O4
Molar mass	402.495 g·mol−1
Chirality	Racemic mixture
InChI InChI=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) Y Key:ZDLBNXXKDMLZMF-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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.

Synthesis

Cinitapride is the amide formed by reacting methyl 4-amino-2-ethoxy-5-nitrobenzoate (1) with the 4-aminopiperidine derivative (2).^[5][6]

References

1. Robert M, Salvà M, Segarra R, et al. (July 2007). "The prokinetic cinitapride has no clinically relevant pharmacokinetic interaction and effect on QT during coadministration with ketoconazole". Drug Metabolism and Disposition. 35 (7): 1149–56. doi:10.1124/dmd.106.010835. PMID 17437965. S2CID 1284844.
2. Fernández AG, Massingham R (January 1985). "Peripheral receptor populations involved in the regulation of gastrointestinal motility and the pharmacological actions of metoclopramide-like drugs". Life Sciences. 36 (1): 1–14. doi:10.1016/0024-3205(85)90280-2. PMID 2981378.
3. Alarcón-de-la-Lastra Romero C, López A, Martín MJ, la Casa C, Motilva V (April 1997). "Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds". Pharmacology. 54 (4): 193–202. doi:10.1159/000139487. PMID 9211565.
4. Alarcón de la Lastra C, La Casa C, Martin MJ, Motilva V (March 1998). "Effects of cinitapride on gastric ulceration and secretion in rats". Inflammation Research. 47 (3): 131–6. doi:10.1007/s000110050301. PMID 9562338. S2CID 25620004. Archived from the original on 1999-08-27. Retrieved 2010-02-27.
5. GB patent 1574419, Inglesias, J.B; Soto, J.P; Noverola, A.V; Mauri, J.M, "Piperidine compounds", issued 1980-09-03, assigned to Anphar SA
6. "Cinitapride". Thieme. Retrieved 2024-07-02.