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).
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: acamprosate

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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)
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