2344. Clebopride

Nomenclature

CAS number: 55905-53-8
4-Amino-5-chloro-2-methoxy-N-[1-(phenylmethyl)-4-piperidinyl]benzamide; 4-amino-N-(1-benzyl-4-piperidyl)-5-chloro-o-anisamide; N-(1′-benzyl-4′-piperidyl)-2-methoxy-4-amino-5-chlorobenzamide.
C20H24ClN3O2; mol wt 373.88.
C 64.25%, H 6.47%, Cl 9.48%, N 11.24%, O 8.56%.

Description and 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).

Chemical structure

Properties

Cryst from methanol, mp 194-195°.

Derivative

Hydrochloride monohydrate.
C20H24ClN3O2.HCl.H2O; mol wt 428.35.
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).

Derivative

Malate.

Nomenclature

CAS number: 57645-91-7
Amicos (Banyu); Clanzol (Orfi Farma); Clast (Meiji Seika); Cleboril (Almirall-Omega); Cleprid (Recordati); Motilex (Guidotti).
C20H24ClN3O2.C4H6O5; mol wt 507.96.
C 56.75%, H 5.95%, Cl 6.98%, N 8.27%, O 22.05%.

Therapeutic Category

Antiemetic; antispasmodic.

Keywords

Antiemetic; Antispasmodic; Dopamine Receptor Antagonist