amisulpride   

GtoPdb Ligand ID: 963

Synonyms: (±)-amisulpride | Barhemsys®
amisulpride is an approved drug
Compound class: Synthetic organic
Comment: The approved drug amisulpride is a racemic mixture of (+)-amisulpride and (-)-amisulpride. The structure shown here does not specify stereochemistry and represents the mixture. The links to external resources in the table above all match the INN-assigned compound amisulpride without stereochemistry specified. Alternative stereoisomers are represented by CID 5746246 and CID 3055076.

The INN-assigned compound sultopride has a similar but distinct structure to amisulpride; however the nomenclature for these two compounds is sometimes used interchangeably on other resources.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 110.11
Molecular weight 369.17
XLogP 2.08
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCN1CCCC1CNC(=O)c1cc(c(cc1OC)N)S(=O)(=O)CC
Isomeric SMILES CCN1CCCC1CNC(=O)c1cc(c(cc1OC)N)S(=O)(=O)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)
InChI Key NTJOBXMMWNYJFB-UHFFFAOYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
D2 receptor Hs Antagonist Antagonist 7.8 – 8.0 pKi - 1-3
pKi 7.9 – 8.0 [1-2]
pKi 7.8 [3]
D3 receptor Rn Antagonist Antagonist 7.4 pKi - 3
pKi 7.4 [3]