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acamprosate   Click here for help

GtoPdb Ligand ID: 7106

Synonyms: Campral®
Approved drug
acamprosate is an approved drug (FDA (2004))
Compound class: Synthetic organic
Comment: Acamprosate is a NMDA glutamate receptor antagonist and a positive allosteric modulator of GABAA receptors.
Marketed formulations contain acamprosate calcium (PubChem CID 155434).
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View more information in the IUPHAR Pharmacology Education Project: acamprosate

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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Click here for structure editor
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 5
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 95.34
Molecular weight 181.04
XLogP -0.63
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 CC(=NCCCS(=O)(=O)O)O
Isomeric SMILES CC(=NCCCS(=O)(=O)O)O
InChI InChI=1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)
InChI Key AFCGFAGUEYAMAO-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. US FDA (2004)
IUPAC Name Click here for help
N-(3-sulfopropyl)ethanimidic acid
International Nonproprietary Names Click here for help
INN number INN
6473 acamprosate
Synonyms Click here for help
Campral®
Database Links Click here for help
CAS Registry No. 77337-76-9
ChEBI CHEBI:51041
ChEMBL Ligand CHEMBL1201293
DrugBank Ligand DB00659
DrugCentral Ligand 38
GtoPdb PubChem SID 178103683
PubChem CID 71158
Search Google for chemical match using the InChIKey AFCGFAGUEYAMAO-UHFFFAOYSA-N
Search Google for chemicals with the same backbone AFCGFAGUEYAMAO
Search PubMed clinical trials acamprosate
Search PubMed titles acamprosate
Search PubMed titles/abstracts acamprosate
UniChem Compound Search for chemical match using the InChIKey AFCGFAGUEYAMAO-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey AFCGFAGUEYAMAO-UHFFFAOYSA-N
Wikipedia acamprosate