Sulpiride

Title: Sulpiride
CAS Registry Number: 15676-16-1
CAS Name: 5-(Aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide
Additional Names: 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
Additional Names: 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.
Sulprofos Sulprostone Sultamicillin Sulthiame Sultopride

Sulpiride
Sulpiride2DACS3.svg
Sulpiride3Dan.gif
Systematic (IUPAC) name
(±)-5-(aminosulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide
Clinical data
Trade names Dolmatil, Sulparex (discontinued), Sulpor
AHFS/Drugs.com International Drug Names
Legal status POM (UK)
Rx-only
Routes Oral
Pharmacokinetic data
Bioavailability 25–40%[1][2]
Protein binding <40%[1]
Metabolism Not metabolised[3]
Half-life 6-8 hours[1]
Excretion Renal (70-90%),[2] Faecal (~95% as the unchanged drug)[1]
Identifiers
CAS number 15676-16-1 YesY
ATC code N05AL01
PubChem CID 5355
IUPHAR ligand 5501
DrugBank DB00391
ChemSpider 5162 YesY
UNII 7MNE9M8287 YesY
KEGG D01226 YesY
ChEMBL CHEMBL26 YesY
Chemical data
Formula C15H23N3O4S 
Mol. mass 341.427 g/mol
 YesY (what is this?)  (verify)

Sulpiride (sold as Dogmatil (HK, SG, PH), Dolmatil (IE, UK), Eglonyl (RU, ZA), Espiride (ZA), Modal (IL), Sulpor (UK), many others) is an atypical antipsychotic drug (although some texts have referred to it as a typical antipsychotic[4]) of the benzamide class used mainly in the treatment of psychosis associated with schizophrenia and major depressive disorder. Sulpiride is more commonly used in Europe, Russia and Japan. Levosulpiride is its purified levo- isomer and is sold in India for similar purpose. So far it has not been approved in the United States, Canada and Australia. The drug has strong chemical and clinical similarities to the related antipsychotic amisulpride.