U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C5H11NO4S
Molecular Weight 181.21
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Acamprosate

SMILES

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

InChI

InChIKey=AFCGFAGUEYAMAO-UHFFFAOYSA-N
InChI=1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)

HIDE SMILES / InChI

Molecular Formula C5H11NO4S
Molecular Weight 181.21
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Acamprosate was the third medication, after disulfiram and naltrexone, to receive U.S. Food and Drug Administration (FDA) approval for postwithdrawal maintenance of alcohol abstinence. The French pharmaceutical company Laboratoires Meram began clinical development and testing of acamprosate in 1982. From 1982 to 1988, acamprosate was tested for safety and for efficacy as a treatment for alcohol dependence. Based on these studies, in 1989 Laboratoires Meram was granted marketing authorization for acamprosate in France under the trade name Aotal®. Since then, acamprosate has been extensively used and studied throughout Europe and, subsequently, in the United States. Although acamprosate has been used in Europe for more than 20 years, it was not approved by FDA until July 2004. Acamprosate became available for use in the United States in January 2005, under the trade name Campral® Delayed-Release Tablets (Merck Santé, a subsidiary of Merck KGaA, Darmstadt, Germany). Campral is currently marketed in the United States by Forest Pharmaceuticals. 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. It seems to inhibit NMDA receptors while activating GABA receptors.

CNS Activity

Curator's Comment: Chronic alcohol intake alters the balance of excitatory (e.g. glutamate) and inhibitory (e.g. gamma amino butyric acid) and amino acids within the brain. Acamprosate crosses the blood brain barrier and is thought to act by complex neuromodulatory processes to restore the balance, especially the inhibition of glutamate which is thought to have an important role in dependency. It reduces craving and therefore the risk of relapse.

Originator

Curator's Comment: The French pharmaceutical company Laboratoires Meram began clinical development and testing of acamprosate in 1982.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Acamprosate

Approved Use

Acamprosate calcium delayed-release tablets are indicated for the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation. Treatment with Acamprosate calcium delayed-release tablets should be part of a comprehensive management program that includes psychosocial support.

Launch Date

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
244.64 ng/mL
666 mg single, oral
dose: 666 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACAMPROSATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3829.56 ng × h/mL
666 mg single, oral
dose: 666 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACAMPROSATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.26 h
666 mg single, oral
dose: 666 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACAMPROSATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Disc. AE: Diarrhea, Nausea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (2%)
Nausea (<1%)
Depression (<1%)
Anxiety (<1%)
Sources:
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Disc. AE: Pain, Constipation...
AEs leading to
discontinuation/dose reduction:
Pain (<1%)
Constipation (<1%)
Somnolence (<1%)
Insomnia (<1%)
Impotence (<1%)
Sources:
56 g single, oral
Overdose
Dose: 56 g
Route: oral
Route: single
Dose: 56 g
Sources:
unknown
Other AEs: Diarrhea...
66 mg 3 times / day steady, oral
Dose: 66 mg, 3 times / day
Route: oral
Route: steady
Dose: 66 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Anaphylactoid reaction, Diffuse pain...
Other AEs:
Anaphylactoid reaction (serious, 1 patient)
Diffuse pain (below serious, 2 patients)
Suicidal ideation (below serious, 2 patients)
Tremor (below serious, 2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea 2%
Disc. AE
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Anxiety <1%
Disc. AE
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Depression <1%
Disc. AE
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Nausea <1%
Disc. AE
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Constipation <1%
Disc. AE
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Impotence <1%
Disc. AE
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Insomnia <1%
Disc. AE
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Pain <1%
Disc. AE
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Somnolence <1%
Disc. AE
666 mg 3 times / day steady, oral
Recommended
Dose: 666 mg, 3 times / day
Route: oral
Route: steady
Dose: 666 mg, 3 times / day
Sources:
unhealthy, adult
Diarrhea
56 g single, oral
Overdose
Dose: 56 g
Route: oral
Route: single
Dose: 56 g
Sources:
unknown
Diffuse pain below serious, 2 patients
66 mg 3 times / day steady, oral
Dose: 66 mg, 3 times / day
Route: oral
Route: steady
Dose: 66 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Suicidal ideation below serious, 2 patients
66 mg 3 times / day steady, oral
Dose: 66 mg, 3 times / day
Route: oral
Route: steady
Dose: 66 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Tremor below serious, 2 patients
66 mg 3 times / day steady, oral
Dose: 66 mg, 3 times / day
Route: oral
Route: steady
Dose: 66 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Anaphylactoid reaction serious, 1 patient
66 mg 3 times / day steady, oral
Dose: 66 mg, 3 times / day
Route: oral
Route: steady
Dose: 66 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victimTox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Buprenorphine and a CRF1 antagonist block the acquisition of opiate withdrawal-induced conditioned place aversion in rats.
2005-01
A comparison of two intensities of psychosocial intervention for alcohol dependent patients treated with acamprosate.
2004-04-15
Prevention of relapse to addiction: information for the practitioner.
2004-02
Effect of the combination of naltrexone and acamprosate on alcohol intake in mice.
2004-02
Neurochemical changes of the extracellular concentrations of glutamate and aspartate in the nucleus accumbens of rats after chronic administration of morphine.
2004-01-12
Acamprosate in alcohol dependence: a randomized controlled efficacy study in a standard clinical setting.
2004-01
Improvement in quality of life after treatment for alcohol dependence with acamprosate and psychosocial support.
2004-01
The efficacy of acamprosate in the maintenance of abstinence in alcohol-dependent individuals: results of a meta-analysis.
2004-01
NR2B subunit selective NMDA antagonists inhibit neurotoxic effect of alcohol-withdrawal in primary cultures of rat cortical neurones.
2004-01
[Acamprosate (Aotal): could adverse effects upset the treatment of alcohol dependence?].
2003-12-19
Does acamprosate improve reduction of drinking as well as aiding abstinence?
2003-12
Acamprosate and naltrexone treatment for alcohol dependence: an evidence-based risk-benefits assessment.
2003-12
Caroverine inhibits the conditioned place aversion induced by naloxone-precipitated morphine withdrawal in rats.
2003-10-02
Acamprosate blocks the increase in dopamine extracellular levels in nucleus accumbens evoked by chemical stimulation of the ventral hippocampus.
2003-10
[Psychosocial treatment plus drug prophylaxis. Fewer recurrences after alcohol withdrawal].
2003-09-04
Efficacy of acamprosate in the treatment of alcohol-dependent outpatients.
2003-09
New pharmacotherapies for alcohol dependence: are they being used and what do they cost?
2003-08-18
Effects of naltrexone alone and in combination with acamprosate on the alcohol deprivation effect in rats.
2003-08
Acamprosate for the adjunctive treatment of alcohol dependence.
2003-07-05
[The role of the glutamatergic system in alcohol addiction].
2003-07
Testing combined pharmacotherapies and behavioral interventions for alcohol dependence (the COMBINE study): a pilot feasibility study.
2003-07
Testing combined pharmacotherapies and behavioral interventions in alcohol dependence: rationale and methods.
2003-07
The effect of acamprosate on the development of morphine-induced behavioral sensitization in rats.
2003-07
A pilot study on the effects of treatment with acamprosate on craving for alcohol in alcohol-dependent patients.
2003-06
Dose-ranging kinetics and behavioral pharmacology of naltrexone and acamprosate, both alone and combined, in alcohol-dependent subjects.
2003-06
Acamprosate does not induce a conditioned place preference and reveals no state-dependent effects in this paradigm.
2003-06
Acamprosate and its efficacy in treating alcohol dependent adolescents.
2003-06
[Preventing recurrence after alcohol withdrawal treatment with drugs. Reducing the drive to drink].
2003-05-08
Physicians' opinions about medications to treat alcoholism.
2003-05
Cost-effectiveness of adjuvant treatment with acamprosate in maintaining abstinence in alcohol dependent patients.
2003-04
Acamprosate in Korean alcohol-dependent patients: a multi-centre, randomized, double-blind, placebo-controlled study.
2003-03-14
Effects of acamprosate on excitatory amino acids during multiple ethanol withdrawal periods.
2003-03
Local acamprosate modulates dopamine release in the rat nucleus accumbens through NMDA receptors: an in vivo microdialysis study.
2003-02
[Deficits in preventing recurrence in alcoholic patients. Withdrawal--and immediately back to the bottle].
2003-01-16
The anti-relapse compound acamprosate inhibits the development of a conditioned place preference to ethanol and cocaine but not morphine.
2003-01
Comparing and combining naltrexone and acamprosate in relapse prevention of alcoholism: a double-blind, placebo-controlled study.
2003-01
Use of acamprosate and opioid antagonists in the treatment of alcohol dependence: a European perspective.
2003
Current pharmacotherapies of alcoholism: a U.S. perspective.
2003
Pharmacological mechanisms of naltrexone and acamprosate in the prevention of relapse in alcohol dependence.
2003
[Drug therapy of alcohol dependence--a critical review].
2003
[Neural basis of alcohol dependence].
2003
Pharmacology of acamprosate: an overview.
2003
The anti-craving taurine derivative acamprosate: failure to extinguish morphine conditioned place preference.
2003
Research advances in the understanding and treatment of addiction.
2003
Acamprosate.
2003
Alcohol misuse and dependence. Assessment and management.
2002-12
Acamprosate inhibits the binding and neurotoxic effects of trans-ACPD, suggesting a novel site of action at metabotropic glutamate receptors.
2002-12
The European NEAT program: an integrated approach using acamprosate and psychosocial support for the prevention of relapse in alcohol-dependent patients with a statistical modeling of therapy success prediction.
2002-10
Acamprosate, MK-801, and ifenprodil inhibit neurotoxicity and calcium entry induced by ethanol withdrawal in organotypic slice cultures from neonatal rat hippocampus.
2002-10
Interactions between taurine and ethanol in the central nervous system.
2002
Patents

Sample Use Guides

The recommended dose of CAMPRAL (Acamprosate) is two 333 mg tablets (each dose should total 666 mg) taken three times daily. Although dosing may be done without regard to meals, dosing with meals was employed during clinical trials and is suggested as an aid to compliance in those patients who regularly eat three meals daily. A lower dose may be effective in some patients. Treatment with CAMPRAL should be initiated as soon as possible after the period of alcohol withdrawal, when the patient has achieved abstinence, and should be maintained if the patient relapses. CAMPRAL should be used as part of a comprehensive psychosocial treatment program.
Route of Administration: Oral
In Vitro Use Guide
Acamprosate (0.1-1 mM) added to the perfusion fluid in vitro reduced excitatory and inhibitory postsynaptic potentials and the depolarizing responses evoked by iontophoretic application of the excitatory amino acids, L-glutamate, L-aspartate, L-homocysteate and N-methyl-D-aspartate, but did not alter the responses to gamma-aminobutyric acid in rat neocortical neurons.
Substance Class Chemical
Created
by admin
on Wed Apr 02 07:48:18 GMT 2025
Edited
by admin
on Wed Apr 02 07:48:18 GMT 2025
Record UNII
N4K14YGM3J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AOTAL
Preferred Name English
Acamprosate
HSDB   INN   VANDF   WHO-DD  
INN  
Official Name English
Acamprosate [WHO-DD]
Common Name English
3-(Acetylamino)propane-1-sulfonate
Systematic Name English
Acamprosate [INN]
Common Name English
1-Propanesulfonic acid, 3-(acetylamino)-
Systematic Name English
Acamprosate [VANDF]
Common Name English
Acamprosate [HSDB]
Common Name English
3-(Acetylamino)-1-propanesulfonic acid
Systematic Name English
3-(Acetylamino)propane-1-sulphonate
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 392413
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
WHO-ATC N07BB03
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
WHO-VATC QN07BB03
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
NCI_THESAURUS C1509
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
LIVERTOX NBK548677
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
Code System Code Type Description
INN
6473
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
ECHA (EC/EINECS)
278-667-4
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
MESH
C043877
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
PUBCHEM
71158
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
DRUG CENTRAL
38
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
HSDB
7358
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
EPA CompTox
DTXSID3044259
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
CHEBI
51041
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
IUPHAR
7106
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
FDA UNII
N4K14YGM3J
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201293
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
SMS_ID
100000082346
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
RXCUI
82819
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
Acamprosate
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
DRUG BANK
DB00659
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
CAS
77337-76-9
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
NCI_THESAURUS
C81691
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
DAILYMED
N4K14YGM3J
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
EVMPD
SUB07366MIG
Created by admin on Wed Apr 02 07:48:18 GMT 2025 , Edited by admin on Wed Apr 02 07:48:18 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
TRANSPORTER -> SUBSTRATE
EXCRETED UNCHANGED
URINE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC AT STEADY-STATE

Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC