amisulpride   Click here for help

GtoPdb Ligand ID: 963

Synonyms: (±)-amisulpride | Barhemsys®
Approved drug
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: amisulpride

amisulpride is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide
International Nonproprietary Names Click here for help
INN number INN
4960 amisulpride
Synonyms Click here for help
(±)-amisulpride | Barhemsys®
Database Links Click here for help
Specialist databases
GPCRdb Ligand amisulpride
Other databases
BindingDB Ligand 81790
CAS Registry No. 71675-85-9 (source: Scifinder)
ChEBI CHEBI:64045
ChEMBL Ligand CHEMBL243712
DrugBank Ligand DB06288
DrugCentral Ligand 179
GtoPdb PubChem SID 135649938
Immunopaedia Search amisulpride
PubChem CID 2159
Search Google for chemical match using the InChIKey NTJOBXMMWNYJFB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone NTJOBXMMWNYJFB
Search PubMed clinical trials amisulpride
Search PubMed titles amisulpride
Search PubMed titles/abstracts amisulpride
UniChem Compound Search for chemical match using the InChIKey NTJOBXMMWNYJFB-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey NTJOBXMMWNYJFB-UHFFFAOYSA-N
Wikipedia Amisulpride

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MedChemExpress
Amisulpride (links to external site)
Cat. No. HY-14545