Amisulpride

Amisulpride
Clinical data
Trade names	Socian, Barhemsys, others
Other names	Aminosultopride; AST; APD-421; APD421; APD-403; APD403; DAN-2163; DAN2163
AHFS/Drugs.com	Monograph
License data	US DailyMed: Amisulpride; US FDA: Barhemsys;
Pregnancy; category	AU: C;
Routes of; administration	By mouth, intravenous
Drug class	Dopamine D2 and D3 receptor antagonist; Serotonin 5-HT2B and 5-HT7 receptor antagonist; Antipsychotic; Antidepressant; Antiemetic
ATC code	N05AL05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	48%
Protein binding	16%
Metabolism	Liver (minimal; most excreted unchanged)
Elimination half-life	12 hours
Excretion	Kidney (23–46%), Faecal
Identifiers
	IUPAC name (RS)-4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide;
CAS Number	71675-85-9 ;
PubChem CID	2159;
IUPHAR/BPS	963;
DrugBank	DB06288 ;
ChemSpider	2074 ;
UNII	8110R61I4U;
KEGG	D07310 ;
ChEBI	CHEBI:64045 ;
ChEMBL	ChEMBL243712 ;
CompTox Dashboard (EPA)	DTXSID5042613 ;
ECHA InfoCard	100.068.916
Chemical and physical data
Formula	C17H27N3O4S
Molar mass	369.48 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(=O)(c1cc(c(OC)cc1N)C(=O)NCC2N(CC)CCC2)CC;
	InChI InChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21) ; Key:NTJOBXMMWNYJFB-UHFFFAOYSA-N ;
	(verify)

Amisulpride, sold under the brand names Socian and Barhemsys, is a medication used in the treatment of schizophrenia, acute psychotic episodes, depression, and nausea and vomiting. It is specifically used at lower doses intravenously to prevent and treat postoperative nausea and vomiting; at low doses by mouth to treat depression; and at higher doses by mouth to treat psychosis.

It is usually classed with the atypical antipsychotics. Chemically it is a benzamide and like other benzamide antipsychotics, such as sulpiride, it is associated with a high risk of elevating blood levels of the lactation hormone, prolactin (thereby potentially causing the absence of the menstrual cycle, breast enlargement, even in males, breast milk secretion not related to breastfeeding, impaired fertility, impotence, breast pain, etc.), and a low risk, relative to the typical antipsychotics, of causing movement disorders.

Amisulpride is indicated for use in the United States in adults for the prevention of postoperative nausea and vomiting (PONV), either alone or in combination with an antiemetic of a different class; and to treat PONV in those who have received antiemetic prophylaxis with an agent of a different class or have not received prophylaxis.

Amisulpride is believed to work by blocking, or antagonizing, the dopamine D₂ receptor, reducing its signalling. The effectiveness of amisulpride in treating dysthymia and the negative symptoms of schizophrenia is believed to stem from its blockade of the presynaptic dopamine D₂ and D₃ autoreceptors. These presynaptic receptors regulate the release of dopamine into the synapse, so by blocking them amisulpride increases dopamine concentrations in the synapse. This increased dopamine concentration is theorized to act on dopamine D₁ receptors to relieve depressive symptoms (in dysthymia) and the negative symptoms of schizophrenia.

It was introduced by Sanofi-Aventis in the 1990s. Its patent expired by 2008, and generic formulations became available. It is marketed in all English-speaking countries except for Canada.