Topic summary

Amisulpride

Clinical dataTrade namesSocian, Barhemsys, othersOther namesAminosultopride; AST; APD-421; APD421; APD-403; APD403; DAN-2163; DAN2163AHFS/Drugs.comMonographLicense dataPregnancy
category
  • AU: C
Routes of
administration
By mouth, intravenousDrug classDopamineD2 and D3 receptorantagonist; Serotonin5-HT2B and 5-HT7 receptorantagonist; Antipsychotic; Antidepressant; AntiemeticATC codeLegal statusLegal status
Pharmacokinetic dataBioavailability48%Protein binding16%MetabolismLiver (minimal; most excreted unchanged)Elimination half-life12 hoursExcretionKidney (23–46%), FaecalIdentifiers
  • (RS)-4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide
CAS NumberPubChemCIDIUPHAR/BPSDrugBankChemSpiderUNIIKEGGChEBIChEMBLCompTox Dashboard(EPA)ECHA InfoCard100.068.916Chemical and physical dataFormulaC17H27N3O4SMolar mass369.48 g·mol3D model (JSmol)
  • O=S(=O)(c1cc(c(OC)cc1N)C(=O)NCC2N(CC)CCC2)CC
  • 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
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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 D3autoreceptors. 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 dopamineD1 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.