Acamprosate (CHEM002242)

Record Information
Version1.0
Creation Date2009-07-21 20:27:22 UTC
Update Date2026-05-14 16:45:19 UTC
Accession NumberCHEM002242
Identification
Common NameAcamprosate
ClassSmall Molecule
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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Alcohol Deterrent
  • Amide
  • Amine
  • Drug
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Acetamido-1-propanesulfonic acidChEBI
AcamprosatoChEBI
AcamprosatumChEBI
N-AcetylhomotaurineChEBI
AotalKegg
3-Acetamido-1-propanesulfonateGenerator
3-Acetamido-1-propanesulphonateGenerator
3-Acetamido-1-propanesulphonic acidGenerator
Acamprosic acidGenerator
3-(Acetylamino)propanesulphonic acidHMDB
CampralHMDB
Campral ecHMDB
N-Acetylhomotaurine, monopotassium saltHMDB
N-Acetylhomotaurine, zinc (2:1) saltHMDB
RegtectHMDB
Acamprosate calciumHMDB
N-Acetylhomotaurine, calcium (2:1) saltHMDB
N-Acetylhomotaurine, magnesium (2:1) saltHMDB
N-Acetylhomotaurine, monolithium saltHMDB
N-Acetylhomotaurine, monosodium saltHMDB
ZulexHMDB
Calcium acetyl homotaurinateHMDB
Calcium acetylhomotaurineHMDB
Sodium acetylhomotaurineHMDB
AOTAHMDB
AcamprostateHMDB
Calcium acetylhomotaurinateHMDB
Acetyl homotaurinate, calciumHMDB
Acetylhomotaurinate, calciumHMDB
N Acetylhomotaurine, monolithium saltHMDB
Acetylhomotaurine, calciumHMDB
Acetylhomotaurine, sodiumHMDB
N Acetylhomotaurine, monosodium saltHMDB
N AcetylhomotaurineHMDB
N Acetylhomotaurine, monopotassium saltHMDB
Chemical FormulaC5H11NO4S
Average Molecular Mass181.210 g/mol
Monoisotopic Mass181.041 g/mol
CAS Registry Number77337-76-9
IUPAC Name3-acetamidopropane-1-sulfonic acid
Traditional Nameacamprosate
SMILESCC(=O)NCCCS(O)(=O)=O
InChI IdentifierInChI=1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)
InChI KeyAFCGFAGUEYAMAO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
Substituents
  • Organosulfonic acid
  • Sulfonyl
  • Alkanesulfonic acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility1.88e+01 g/L
Predicted Properties
PropertyValueSource
Water Solubility18.8 g/LALOGPS
logP-1.8ALOGPS
logP-2.8ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)-1.1ChemAxon
pKa (Strongest Basic)-0.47ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.91 m³·mol⁻¹ChemAxon
Polarizability17.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureThe 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.
Mechanism of ToxicityThe 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.
MetabolismAcamprosate does not undergo metabolism. Route of Elimination: Following oral administration of CAMPRAL™, the major route of excretion is via the kidneys as acamprosate. Half Life: 20 - 33 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsIn 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.
TreatmentTreatment consists of discontinuation of Acamprosate together with appropriate symptomatic therapy. The judicious use of a cardioselective beta-receptor blocker may beconsidered, bearing in mind that such medication can produce bronchospasm. (8)
Concentrations
Not Available
External Links
DrugBank IDDB00659
HMDB IDHMDB0014797
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcamprosate
Chemspider ID64300
ChEBI ID51041
PubChem Compound ID71158
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Tsai G, Coyle JT: The role of glutamatergic neurotransmission in the pathophysiology of alcoholism. Annu Rev Med. 1998;49:173-84.
2. Mason BJ: Treatment of alcohol-dependent outpatients with acamprosate: a clinical review. J Clin Psychiatry. 2001;62 Suppl 20:42-8.
3. Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80.
4. Feeney GF, Connor JP, Young RM, Tucker J, McPherson A: Combined acamprosate and naltrexone, with cognitive behavioural therapy is superior to either medication alone for alcohol abstinence: a single centres' experience with pharmacotherapy. Alcohol Alcohol. 2006 May-Jun;41(3):321-7. Epub 2006 Feb 8.
5. Mason BJ, Goodman AM, Chabac S, Lehert P: Effect of oral acamprosate on abstinence in patients with alcohol dependence in a double-blind, placebo-controlled trial: the role of patient motivation. J Psychiatr Res. 2006 Aug;40(5):383-93. Epub 2006 Mar 20.