Clebopride

Clebopride
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A03FA06 (WHO) ;
Identifiers
	IUPAC name 4-amino-N-(1-benzylpiperidin-4-yl)-5-chloro-; 2-methoxybenzamide;
CAS Number	55905-53-8 ;
PubChem CID	2780;
ChemSpider	2678 ;
UNII	I0A84520Y9;
KEGG	D03534 ;
ChEMBL	ChEMBL325109 ;
CompTox Dashboard (EPA)	DTXSID7022831 ;
ECHA InfoCard	100.054.424
Chemical and physical data
Formula	C20H24ClN3O2
Molar mass	373.876 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1cc(c(OC)cc1N)C(=O)NC3CCN(Cc2ccccc2)CC3;
	InChI InChI=1S/C20H24ClN3O2/c1-26-19-12-18(22)17(21)11-16(19)20(25)23-15-7-9-24(10-8-15)13-14-5-3-2-4-6-14/h2-6,11-12,15H,7-10,13,22H2,1H3,(H,23,25) ; Key:BVPWJMCABCPUQY-UHFFFAOYSA-N ;
	(verify)

Clebopride is a dopamine antagonist drug with antiemetic and prokinetic properties used to treat functional gastrointestinal disorders. Chemically, it is a substituted benzamide, closely related to metoclopramide.

A small Spanish study found that more adverse reactions are reported with clebopride than with metoclopramide, particularly extrapyramidal symptoms.^[1]

Synthesis

Dopamine receptor antagonist related to metoclopramide, q.v.

The benzoic acid moiety common to many of the benzamides is prepared in a straightforward manner from the methyl ether of 4-aminosalicylic acid 1. Acetylation on nitrogen followed by chlorination gives intermediate 3; benzoic acid 4 is then obtained by removal of the acetyl group. Condensation of this acid with an aminopiperidine could be achieved by means of the mixed anhydride (prepared by reaction with ethyl chloroformate), which affords clebopride (5).

References

^ Cuena Boy R, Maciá Martínez MA (1998). "[Extrapyramidal toxicity caused by metoclopramide and clebopride: study of voluntary notifications of adverse effects to the Spanish Drug Surveillance System]". Atencion Primaria (in Spanish). 21 (5): 289–95. PMID 9608114. Free full text
^ R. G. Spickett et al., DE 2513136 ; A. V. Noverola et al., U.S. patent 4,138,492 (1975, 1979 both to Anphar).
^ Template:Cite PMID

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[1] Cuena Boy R, Maciá Martínez MA (1998). "[Extrapyramidal toxicity caused by metoclopramide and clebopride: study of voluntary notifications of adverse effects to the Spanish Drug Surveillance System]". Atencion Primaria (in Spanish). 21 (5): 289–95. PMID 9608114. Free full text

[2] R. G. Spickett et al., DE 2513136 ; A. V. Noverola et al., U.S. patent 4,138,492 (1975, 1979 both to Anphar).

[3] Template:Cite PMID

[1]

[2]

[3]

Synthesis

See also

References