Clebopride

Title: Clebopride
CAS Registry Number: 55905-53-8
CAS Name: 4-Amino-5-chloro-2-methoxy-N-[1-(phenylmethyl)-4-piperidinyl]benzamide
Additional Names: 4-amino-N-(1-benzyl-4-piperidyl)-5-chloro-o-anisamide; N-(1¢-benzyl-4¢-piperidyl)-2-methoxy-4-amino-5-chlorobenzamide
Molecular Formula: C20H24ClN3O2
Molecular Weight: 373.88
Percent Composition: C 64.25%, H 6.47%, Cl 9.48%, N 11.24%, O 8.56%
Literature References: Dopamine receptor antagonist related to metoclopramide, q.v. Prepn: R. G. Spickett et al., DE 2513136; A. V. Noverola et al., US 4138492 (1975, 1979 both to Anphar); J. Prieto et al., J. Pharm. Pharmacol. 29, 147 (1977). Pharmacological study: J. L. Masso, D. J. Roberts, ibid. 32, 727 (1980). In vitro metabolism studies: G. Huizing et al., Xenobiotica 10, 211 (1980); G. Huizing, A. H. Beckett, ibid. 593. Pharmacokinetics: J. Segura et al., J. Pharm. Pharmacol. 33, 214 (1981). Comparative study of anti-emetic and gastrointestinal effects: P. Berga et al., Arch. Farmacol. Toxicol. 7, 189 (1981). Efficacy in healing exptl ulcers: Y. Matsuo et al., Oyo Yakuri 24, 251 (1982); S. Okabe et al., ibid. 261, C.A. 97, 208081n, 208082p (1982). Determn in urine and plasma by radioimmunoassay: M. Yano et al., Chem. Pharm. Bull. 32, 1491 (1984). Clinical effect in postoperative nausea: D. F. Duarte et al., Clin. Ther. 7, 365 (1985).
Properties: Cryst from methanol, mp 194-195°.
Melting point: mp 194-195°
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C20H24ClN3O2.HCl.H2O
Molecular Weight: 428.35
Percent Composition: C 56.08%, H 6.35%, Cl 16.55%, N 9.81%, O 11.21%
Properties: Cryst, mp 217-219°. Approx oral LD50 in male Swiss mice: >1000 mg/kg (Prieto).
Melting point: mp 217-219°
Toxicity data: Approx oral LD50 in male Swiss mice: >1000 mg/kg (Prieto)
Derivative Type: Malate
CAS Registry Number: 57645-91-7
Trademarks: Amicos (Banyu); Clanzol (Orfi Farma); Clast (Meiji Seika); Cleboril (Almirall-Omega); Cleprid (Recordati); Motilex (Guidotti)
Molecular Formula: C20H24ClN3O2.C4H6O5
Molecular Weight: 507.96
Percent Composition: C 56.75%, H 5.95%, Cl 6.98%, N 8.27%, O 22.05%
Therap-Cat: Antiemetic; antispasmodic.
Keywords: Antiemetic; Antispasmodic; Dopamine Receptor Antagonist.
Clemastine Clemizole Clenbuterol Clentiazem Clethodim

Clebopride
Clebopride.svg
Clebopride.png
Systematic (IUPAC) name
4-amino-N-(1-benzylpiperidin-4-yl)-5-chloro-
2-methoxybenzamide
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 55905-53-8 YesY
ATC code A03FA06
PubChem CID 2780
ChemSpider 2678 YesY
UNII I0A84520Y9 YesY
KEGG D03534 YesY
ChEMBL CHEMBL325109 YesY
Chemical data
Formula C20H24ClN3O2 
Mol. mass 373.876 g/mol
 YesY (what is this?)  (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]