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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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/)
No information available.
Summary of Clinical Use Click here for help
Used alongside behavioural therapy to maintain alcohol abstinence in alcohol-dependent patients.
In 2014, the European Medicines Agency granted this drug orphan designation for the treatment of fragile X syndrome [2-3]. A Phase 2/III clinical trial for this indication is underway (NCT01911455). Another Phase 2/III clinical trial is recruiting patients to evaluate any benefit from acamprosate in autism disorder (NCT01813318).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
This drug acts as an antagonist of NMDA glutamate receptors and as a positive allosteric modulator of GABAA receptors. The glutaminergic hypothesis links this neurotransmitter system to alcohol dependence and withdrawal [1]. In addition, cortical and limbic arousal (sympathetic activation) levels are believed to be upregulated during alcohol withdrawal, as a 'bounce-back' response to alcohol-induced down-regulation of GABAA receptors. Acamprosate-potentiated GABAA activity helps to inhibit this elevated arousal. These two mechanisms appear to act together to provide the clinical benefits observed with use of this drug.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01813318 Study of Acamprosate in Autism Phase 2/Phase 3 Interventional Children's Hospital Medical Center, Cincinnati
NCT01911455 Study of Acamprosate in Fragile x Syndrome Phase 2/Phase 3 Interventional Children's Hospital Medical Center, Cincinnati
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com