Drug/Small Molecule:
acamprosate

2D structure

Overview

Generic Names: 3-(Acetylamino)propanesulphonic acid; 3-Acetamido-1-propanesulfonic acid; N-Acetylhomotaurine; acamprosate
IUPAC Name: 3-acetamidopropane-1-sulfonic acid
Trade Names: Campral
PharmGKB Accession Id: PA10344

Description

Acamprosate, also known by the brand name Campral™, is a drug used for treating alcohol dependence. Acamprosate is thought to stabilize the chemical balance in the brain that would otherwise be disrupted by alcoholism, possibly by blocking glutaminergic N-methyl-D-aspartate receptors, while gamma-aminobutyric acid type A receptors are activated. Reports indicate that acamprosate only works with a combination of attending support groups and abstinence from alcohol. Certain serious side effects include allergic reactions, irregular heartbeats, and low or high blood pressure, while less serious side effects include headaches, insomnia, and impotence. Acamprosate should not be taken by people with kidney problems or allergies to the drug.

Indication

For the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation

ATC Therapeutic Category

  • N07BB:Drugs used in alcohol dependence

Pharmacology and Interactions

Mechanism Of Action

The mechanism of action of acamprosate in maintenance of alcohol abstinence is not completely understood. Chronic alcohol exposure is hypothesized to alter the normal balance between neuronal excitation and inhibition. in vitro and in vivo studies in animals have provided evidence to suggest acamprosate may interact with glutamate and GABA neurotransmitter systems centrally, and has led to the hypothesis that acamprosate restores this balance.

Pharmacology

Pharmacodynamic studies have shown that acamprosate calcium reduces alcohol intake in alcohol-dependent animals in a dose-dependent manner and that this effect appears to be specific to alcohol and the mechanisms of alcohol dependence. Acamprosate calcium has negligible observable central nervous system (CNS) activity in animals outside of its effects on alcohol dependence, exhibiting no anticonvulsant, antidepressant, or anxiolytic activity.

Food Interactions

Take without regard to meals. Taking the product with food reduces its Cmax by 42% and total drug exposure by 23% (not considered significant).

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Acamprosate does not undergo metabolism.

Protein Binding

Non detectable

Absorption

The absolute bioavailability of acamprosate after oral administration is about 11%. The food effect on absorption is not clinically significant and no adjustment of dose is necessary.

Half Life

20 - 33 hours

Toxicity

In all reported cases of acute overdosage with acamprosate (total reported doses of up to 56 grams of acamprosate calcium), the only symptom that could be reasonably associated with acamprosate was diarrhea.

Chemical Properties

Chemical Formula:

C5H11NO4S

SMILES Code:

CC(=O)NCCCS(=O)(=O)O

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

181.21 / 181.0409

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00659
KEGG Drug ID:
D02780
PubChem Compound ID:
71158
PubChem Substance ID:
213365

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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