6143. Metoclopramide

Nomenclature

CAS number: 364-62-5
4-Amino-5-chloro-N-[(2-diethylamino)ethyl]-2-methoxybenzamide; 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-o-anisamide; 4-amino-5-chloro-2-methoxy-N-(β-diethylaminoethyl)benzamide; DEL-1267; Elieten (Nippon Kayaku); Eucil (Farmasa); Imperan (Millet); Reliveran (Finadiet).
C14H22ClN3O2; mol wt 299.80.
C 56.09%, H 7.40%, Cl 11.83%, N 14.02%, O 10.67%.

Description and references

Substituted benzamide with neuroleptic activity. Prepn: BE 620543; Thominet, US 3177252 (1962, 1965 to Soc. d'Etudes Sci. Ind. de l'Ile-de-France); R. Pakula et al., Arch. Pharm. 313, 297 (1980). Colorimetric determn in plasma and solubility: G. Pitel, T. Luce, Ann. Pharm. Fr. 23, 673 (1965). Dopamine D2 receptor antagonist (adenylate cyclase independent receptors): J. W. Kebabian, D. B. Calne, Nature 277, 93 (1979). Pharmacology: M. A. Smith, F. J. Salter, Drug Intell. Clin. Pharm. 14, 169 (1980). Pharmacokinetics: H. Vergin et al., Arzneim.-Forsch. 33, 458 (1983). Review of efficacy in psychiatric disorders: E. D. Peselow, M. Stanley, Adv. Biochem. Psychopharmacol. 35, 163-194 (1982); of pharmacology and clinical use: R. A. Harrington et al., Drugs 25, 451-494 (1983); ibid. Suppl. 1, 1-88. Comprehensive description: D. Pitré, R. Stradi, Anal. Profiles Drug Subs. 16, 327-361 (1987).

Chemical structure

Properties

mp 146.5-148°. Soly at 25° (g/100 ml): water 0.02; 95% ethanol 2.30; abs ethanol 1.90; benzene 0.10; chloroform 6.60.

Derivative

Dihydrochloride monohydrate.

Nomenclature

Emetid (Virbac); Gastronerton (Dolorgiet); Primperan (Delagrange).
C14H22ClN3O2.2HCl.H2O; mol wt 390.73.
C 43.03%, H 6.71%, Cl 27.22%, N 10.75%, O 12.28%.

Properties

Crystals, dec 145°. Soly at 25° (g/100 ml): water 48; ethanol (95%) 9; abs ethanol 6; benzene 0.10; chloroform 0.10. Stable in acids solns. Unstable in strongly alkaline solns.

Derivative

Monohydrochloride monohydrate.

Nomenclature

CAS number: 54143-57-6
AHR-3070-C; Cerucal (Temmler); Clopromate (Purdue Frederick); Duraclamid (Durachemie); Emperal (Orion); Gastrese (Wyeth); Gastrobid (Napp); Gastromax (Farmitalia); Gastrosil (Heumann); Gastro-Tablinen (Sanorania); Maxeran (Aventis); Maxolon (GSK); Meclopran (Lagap); Metamide (Protea); Metoclol (Toyama); Metocobil (Vita); Metramid (Nicholas); Moriperan (Morishita); Mygdalon (DDSA); Parmid (Lagap); Paspertin (Kali-Chemie); Peraprin (Taiyo); Plasil (Lepetit); Pramiel (Teikoku Kagaku); Reglan (Wyeth).
C14H22ClN3O2.HCl.H2O; mol wt 354.27.
C 47.46%, H 7.11%, Cl 20.01%, N 11.86%, O 13.55%.

Properties

White crystalline powder, mp 182.5-184°. Sol in water.

Therapeutic Category

Antiemetic.

Keywords

Antiemetic; Dopamine Receptor Antagonist