Amisulpride

Title: Amisulpride
CAS Registry Number: 71675-85-9
CAS Name: 4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide
Additional Names: 4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-o-anisamide; aminosultopride
Manufacturers' Codes: DAN-2163
Trademarks: Deniban (Synthelabo); Socian (Synthelabo); Solian (Synthelabo); Sulamid (Baldacci)
Molecular Formula: C17H27N3O4S
Molecular Weight: 369.48
Percent Composition: C 55.26%, H 7.37%, N 11.37%, O 17.32%, S 8.68%
Literature References: Dopamine receptor antagonist. Prepn: M. Thominet et al., BE 872585; eidem, US 4401822 (1979, 1983 both to Soc. d'Etudes Sci. Ind. de l'Ile-de-France). Crystal structure: H. L. DeWinter et al., Acta Crystallogr. C46, 313 (1990). Psychopharmacology: G. Perrault et al., J. Pharmacol. Exp. Ther. 280, 73 (1997). HPLC determn in plasma and urine: B. Malavasi et al., J. Chromatogr. B 676, 107 (1996). Series of articles on pharmacology and clinical efficacy in schizophrenia: Int. Clin. Psychopharmacol. 12, Suppl. 2, S11-S36 (1997).
Properties: Crystals from acetone, mp 126-127°. LD50 in male mice (mg/kg): 56-60 i.v.; 175-180 i.p.; 224-250 s.c.; 1024-1054 orally (Thominet).
Melting point: mp 126-127°
Toxicity data: LD50 in male mice (mg/kg): 56-60 i.v.; 175-180 i.p.; 224-250 s.c.; 1024-1054 orally (Thominet)
Therap-Cat: Antipsychotic.
Keywords: Antipsychotic; Benzamides; Dopamine Receptor Antagonist.
Amiton Amitriptyline Amitriptylinoxide Amitrole Amixetrine

Amisulpride
Systematic (IUPAC) name
(RS)-4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-
5-ethylsulfonyl-2-methoxy-benzamide
Clinical data
Trade names Solian
AHFS/Drugs.com International Drug Names
Pregnancy cat. C (AU)
Legal status Prescription Only (S4) (AU) POM (UK)
Routes Oral, intramuscular
Pharmacokinetic data
Bioavailability 48%[1][2]
Protein binding 16%[2]
Metabolism Hepatic (minimal; most excreted unchanged)[2]
Half-life 12 hours[1]
Excretion Renal[1] (23-46%),[3][4] Faecal[2]
Identifiers
CAS number 71675-85-9 N
ATC code N05AL05
PubChem CID 2159
IUPHAR ligand 963
DrugBank DB06288
ChemSpider 2074 YesY
UNII 8110R61I4U YesY
KEGG D07310 YesY
ChEMBL CHEMBL243712 YesY
Chemical data
Formula C17H27N3O4S 
Mol. mass 369.48 g/mol
 N (what is this?)  (verify)

Amisulpride (sold as Amazeo, Amipride (AU), Amival, Solian (AU, IE, UK, ZA), Soltus, Sulpitac (IN), Sulprix (AU)), is an atypical antipsychotic used to treat psychosis in schizophrenia and episodes of mania in bipolar disorder. In Italy, it is also used as a treatment for dysthymia.[5]

It was introduced by Sanofi-Aventis in the 1990s. Its patent had expired by 2008 and hence generic formulations are now available.[6]