CAS No 15676-16-1 , N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide

Title: Sulpiride
CAS Registry Number: 15676-16-1
CAS Name: 5-(Aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide
Synonyms: N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-sulfamoyl-o-anisamide; N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-5-sulfamoylbenzamide
Trademarks: Abilit (Sumitomo); Aiglonyl (Fumouze); Coolspan (Hishiyama); Dobren (Ravizza); Dogmatil (Synthelabo); Dogmatyl (Fujisawa); Dolmatil (Lorex); Guastil (Uriach); Meresa (Dolorgiet); Miradol (Mitsui); Mirbanil (Boehringer, Ing.); Misulvan (Bernabo); Neogama (Hormosan); Omperan (Taiho); Pyrikappl (Isei); Sernevin (Toho Yakuhin); Splotin (Taiyo); Sulpitil (Tillotts); Sulpor (Rosemont); Sursumid (Labif); Synédil (Beytout); Trilan (Esseti)
Molecular Formula: C15H23N3O4S
Molecular Weight: 341.43
Percent Composition: C 52.77%, H 6.79%, N 12.31%, O 18.74%, S 9.39%
Literature References: Dopamine D2 and D3-receptor antagonist. Prepn: C. S. Miller et al., US 3342826 (1964 to Soc. d'Etudes Sci. Ind. de l'Ile-de-France); of l-form: F. Mauri, DE 2903891 (1979 to Ravizza), C.A. 91, 211259h (1979). Crystal structure: L. Y. Y. Ma et al., Acta Crystallogr. B38, 2861 (1982). Mechanism of action: P. Jenner et al., J. Pharm. Pharmacol. 32, 39 (1980). Structure-activity study: P. Dostert et al., Eur. J. Med. Chem. - Chim. Ther. 17, 437 (1982). Physical properties: D. Pitrè, E. Valoti, Arch. Pharmacol. 320, 859 (1987). Comprehensive description: D. Pitrè et al., Anal. Profiles Drug Subs. 17, 607-641 (1988). Review of clinical efficacy in psychiatry: A. J. Wagstaff et al., CNS Drugs 2, 313-333 (1994); of levosulpiride in gastroenterology: M. Guslandi, Curr. Ther. Res. 53, 484-501 (1993).
Properties: White, odorless crystalline powder, mp 178-180°. Sparingly sol in methanol. Practically insol in water, ether, chloroform, benzene. pKa1 9.00, pKa2 10.19. [a]D25 -66.8° (c = 0.5 in DMF). LD50 in mice (mg/kg): 170 i.p.; 2250 orally (Dostert).
Melting point: mp 178-180°
pKa: pKa1 9.00, pKa2 10.19
Optical Rotation: [a]D25 -66.8° (c = 0.5 in DMF)
Toxicity data: LD50 in mice (mg/kg): 170 i.p.; 2250 orally (Dostert)
 
Derivative Type: l-Form
CAS Registry Number: 23672-07-3
Synonyms: Levosulpiride; S(-)-sulpiride
Trademarks: Levobren (Knoll); Levopraid (Ravizza)
Properties: Monomorphic crystalline solid, mp 185-187°.
Melting point: mp 185-187°
 
Therap-Cat: Antipsychotic; antidepressant; antiemetic.
Keywords: Antidepressant; Antiemetic; Antipsychotic; Benzamides; Dopamine Receptor Antagonist.