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

Details

Stereochemistry ACHIRAL
Molecular Formula C5H11NO4S
Molecular Weight 181.2114
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACAMPROSATE

SMILES

CC(=NCCCS(=O)(=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 181.2114
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

1.09105919E12
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
n = 1539
Health Status: unhealthy
Condition: alcohol-dependence
Age Group: adult
Population Size: 1539
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: Page: p. 93
unhealthy, adult
n = 1346
Health Status: unhealthy
Condition: alcohol (ethanol)-dependence
Age Group: adult
Population Size: 1346
Sources: Page: p. 93
Disc. AE: Pain, Constipation...
AEs leading to
discontinuation/dose reduction:
Pain (<1%)
Constipation (<1%)
Somnolence (<1%)
Insomnia (<1%)
Impotence (<1%)
Sources: Page: p. 93
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
n = 14
Health Status: unhealthy
Condition: Alcohol Dependence
Population Size: 14
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
n = 1539
Health Status: unhealthy
Condition: alcohol-dependence
Age Group: adult
Population Size: 1539
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
n = 1539
Health Status: unhealthy
Condition: alcohol-dependence
Age Group: adult
Population Size: 1539
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
n = 1539
Health Status: unhealthy
Condition: alcohol-dependence
Age Group: adult
Population Size: 1539
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
n = 1539
Health Status: unhealthy
Condition: alcohol-dependence
Age Group: adult
Population Size: 1539
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: Page: p. 93
unhealthy, adult
n = 1346
Health Status: unhealthy
Condition: alcohol (ethanol)-dependence
Age Group: adult
Population Size: 1346
Sources: Page: p. 93
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: Page: p. 93
unhealthy, adult
n = 1346
Health Status: unhealthy
Condition: alcohol (ethanol)-dependence
Age Group: adult
Population Size: 1346
Sources: Page: p. 93
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: Page: p. 93
unhealthy, adult
n = 1346
Health Status: unhealthy
Condition: alcohol (ethanol)-dependence
Age Group: adult
Population Size: 1346
Sources: Page: p. 93
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: Page: p. 93
unhealthy, adult
n = 1346
Health Status: unhealthy
Condition: alcohol (ethanol)-dependence
Age Group: adult
Population Size: 1346
Sources: Page: p. 93
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: Page: p. 93
unhealthy, adult
n = 1346
Health Status: unhealthy
Condition: alcohol (ethanol)-dependence
Age Group: adult
Population Size: 1346
Sources: Page: p. 93
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
n = 14
Health Status: unhealthy
Condition: Alcohol Dependence
Population Size: 14
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
n = 14
Health Status: unhealthy
Condition: Alcohol Dependence
Population Size: 14
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
n = 14
Health Status: unhealthy
Condition: Alcohol Dependence
Population Size: 14
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
n = 14
Health Status: unhealthy
Condition: Alcohol Dependence
Population Size: 14
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victimTox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Treatment of alcohol-dependent outpatients with acamprosate: a clinical review.
2001
Does the alcoholic's remedy come in a pill?
2001 Aug
The European acamprosate trials: conclusions for research and therapy.
2001 Jan-Feb
Combined behavioral and pharmacologic treatments of alcoholism.
2001 Jul
Mechanisms of alcohol-nicotine interactions: alcoholics versus smokers.
2001 May
The anti-craving compound acamprosate acts as a weak NMDA-receptor antagonist, but modulates NMDA-receptor subunit expression similar to memantine and MK-801.
2001 May
Efficacy of naltrexone and acamprosate for alcoholism treatment: a meta-analysis.
2001 Sep
Acamprosate is neuroprotective against glutamate-induced excitotoxicity when enhanced by ethanol withdrawal in neocortical cultures of fetal rat brain.
2001 Sep
Drug addiction. Part III. Pharmacotherapy of addiction.
2001 Sep-Oct
Relapse prevention and maintaining abstinence in older adults with alcohol-use disorders.
2002
Opioid antagonists for alcohol dependence.
2002
Acamprosate.
2002
Use of acamprosate and different kinds of psychosocial support in relapse prevention of alcoholism. Results from a non-blind, multicentre study.
2002
Potential neuroprotective effects of acamprosate.
2002 Apr
Drug treatments for alcoholism.
2002 Apr
[Acamprosate and psychosocial intervention. An integrative treatment approach for prevention of alcohol dependent patients in Switzerland].
2002 Apr 24
Central nervous system mechanisms in alcohol relapse.
2002 Feb
Effects of acute acamprosate and homotaurine on ethanol intake and ethanol-stimulated mesolimbic dopamine release.
2002 Feb 15
Acceptability and availability of pharmacological interventions for substance misuse by British NHS treatment services.
2002 Jan
New pharmacotherapies for alcohol dependence.
2002 Jul 15
Does psychosocial treatment enhance the efficacy of acamprosate in patients with alcohol problems?
2002 Jul-Aug
Acamprosate decreases the induction of tolerance and physical dependence in morphine-treated mice.
2002 Jun 7
Mesa Grande: a methodological analysis of clinical trials of treatments for alcohol use disorders.
2002 Mar
[Long-term treatment of alcohol dependance].
2002 May
Acamprosate has no effect on NMDA-induced toxicity but reduces toxicity induced by spermidine or by changing the medium in organotypic hippocampal slice cultures from rat.
2002 May
Effects of acamprosate and some polyamine site ligands of NMDA receptor on short-term memory in rats.
2002 May 24
Acamprosate reduces context-dependent ethanol effects.
2002 Oct
A review of chemical agents in the pharmacotherapy of addiction.
2002 Oct
Disposition of acamprosate in the rat: influence of probenecid.
2002 Oct
Cognitive behavioural therapy combined with the relapse-prevention medication acamprosate: are short-term treatment outcomes for alcohol dependence improved?
2002 Oct
[Drug therapy of alcohol dependence--a critical review].
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
Does acamprosate improve reduction of drinking as well as aiding abstinence?
2003 Dec
Acamprosate and naltrexone treatment for alcohol dependence: an evidence-based risk-benefits assessment.
2003 Dec
Comparing and combining naltrexone and acamprosate in relapse prevention of alcoholism: a double-blind, placebo-controlled study.
2003 Jan
The effect of acamprosate on the development of morphine-induced behavioral sensitization in rats.
2003 Jul
Acamprosate for the adjunctive treatment of alcohol dependence.
2003 Jul-Aug
A pilot study on the effects of treatment with acamprosate on craving for alcohol in alcohol-dependent patients.
2003 Jun
Dose-ranging kinetics and behavioral pharmacology of naltrexone and acamprosate, both alone and combined, in alcohol-dependent subjects.
2003 Jun
[Preventing recurrence after alcohol withdrawal treatment with drugs. Reducing the drive to drink].
2003 May 8
Caroverine inhibits the conditioned place aversion induced by naloxone-precipitated morphine withdrawal in rats.
2003 Oct 2
Prevention of relapse to addiction: information for the practitioner.
2004 Feb
Buprenorphine and a CRF1 antagonist block the acquisition of opiate withdrawal-induced conditioned place aversion in rats.
2005 Jan
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 Sat Jun 26 16:33:55 UTC 2021
Edited
by admin
on Sat Jun 26 16:33:55 UTC 2021
Record UNII
N4K14YGM3J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
AOTAL
Brand Name English
1-PROPANESULFONIC ACID, 3-(ACETYLAMINO)-
Common Name English
ACAMPROSATE [VANDF]
Common Name English
ACAMPROSATE [HSDB]
Common Name English
3-(ACETYLAMINO)PROPANE-1-SULPHONATE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 392413
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
WHO-ATC N07BB03
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
WHO-VATC QN07BB03
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
NCI_THESAURUS C1509
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
LIVERTOX 5
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
Code System Code Type Description
INN
6473
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
ECHA (EC/EINECS)
278-667-4
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
MESH
C043877
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
PUBCHEM
71158
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
DRUG CENTRAL
38
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
HSDB
7358
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
EPA CompTox
77337-76-9
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
IUPHAR
7106
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
FDA UNII
N4K14YGM3J
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201293
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
RXCUI
82819
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
Acamprosate
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
DRUG BANK
DB00659
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PRIMARY
CAS
77337-76-9
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
NCI_THESAURUS
C81691
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
EVMPD
SUB07366MIG
Created by admin on Sat Jun 26 16:33:55 UTC 2021 , Edited by admin on Sat Jun 26 16:33:55 UTC 2021
PRIMARY
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