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Identification
NameAcamprosate
Accession NumberDB00659  (APRD00661)
TypeSmall Molecule
GroupsApproved, Investigational
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.

Structure
Thumb
Synonyms
SynonymLanguageCode
3-Acetamido-1-propanesulfonic acidNot AvailableNot Available
AcamprosatoNot AvailableNot Available
AcamprosatumNot AvailableNot Available
N-acetyl homotaurineNot AvailableNot Available
N-AcetylhomotaurineNot AvailableNot Available
Salts
Name/CAS Structure Properties
Acamprosate Calcium
77337-73-6
Thumb
  • InChI Key:
  • Monoisotopic Mass:
  • Average Mass:
DBSALT000002
Brand names
NameCompany
CampralForest Laboratories
RegtectNippon Shinyaku Co., Ltd.
Brand mixturesNot Available
Categories
CAS number77337-76-9
WeightAverage: 181.21
Monoisotopic: 181.040878535
Chemical FormulaC5H11NO4S
InChI KeyAFCGFAGUEYAMAO-UHFFFAOYSA-N
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)
IUPAC Name
3-acetamidopropane-1-sulfonic acid
SMILES
CC(=O)NCCCS(O)(=O)=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassSulfonic Acids and Derivatives
SubclassSulfonic Acids
Direct parentSulfonic Acids
Alternative parentsSulfonyls; Organic Sulfites; Secondary Carboxylic Acid Amides; Polyamines; Enolates; Carboxylic Acids
Substituentscarboxamide group; secondary carboxylic acid amide; carboxylic acid derivative; polyamine; enolate; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the sulfonic acids. These are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R ≠ H).
Pharmacology
IndicationFor the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation
PharmacodynamicsPharmacodynamic 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.
Mechanism of actionThe 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.
AbsorptionThe 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.
Volume of distribution
  • 72 to 109 L
Protein bindingNon detectable
Metabolism

Acamprosate does not undergo metabolism.

Route of eliminationFollowing oral administration of CAMPRAL®, the major route of excretion is via the kidneys as acamprosate.
Half life20 - 33 hours
ClearanceNot Available
ToxicityIn 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.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.5669
Blood Brain Barrier + 0.9764
Caco-2 permeable - 0.6797
P-glycoprotein substrate Non-substrate 0.6973
P-glycoprotein inhibitor I Non-inhibitor 0.9056
P-glycoprotein inhibitor II Non-inhibitor 0.9783
Renal organic cation transporter Non-inhibitor 0.8969
CYP450 2C9 substrate Non-substrate 0.7676
CYP450 2D6 substrate Non-substrate 0.8124
CYP450 3A4 substrate Non-substrate 0.5906
CYP450 1A2 substrate Non-inhibitor 0.877
CYP450 2C9 substrate Non-inhibitor 0.8857
CYP450 2D6 substrate Non-inhibitor 0.9267
CYP450 2C19 substrate Non-inhibitor 0.8726
CYP450 3A4 substrate Non-inhibitor 0.9806
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9614
Ames test Non AMES toxic 0.7031
Carcinogenicity Non-carcinogens 0.5213
Biodegradation Ready biodegradable 0.6698
Rat acute toxicity 1.9578 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9006
hERG inhibition (predictor II) Non-inhibitor 0.878
Pharmacoeconomics
Manufacturers
  • Forest laboratories inc
Packagers
Dosage forms
FormRouteStrength
Tablet, delayed releaseOral333 mg
Prices
Unit descriptionCostUnit
Campral 333 mg Enteric Coated Tabs0.98USDtab
Campral 333 mg dose pak0.95USDeach
Campral dr 333 mg tablet0.95USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP-1.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility18.8ALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.91 m3·mol-1ChemAxon
Polarizability17.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80. Pubmed
  2. Mason BJ: Treatment of alcohol-dependent outpatients with acamprosate: a clinical review. J Clin Psychiatry. 2001;62 Suppl 20:42-8. Pubmed
  3. 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. Pubmed
  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. Pubmed
  5. Tsai G, Coyle JT: The role of glutamatergic neurotransmission in the pathophysiology of alcoholism. Annu Rev Med. 1998;49:173-84. Pubmed
  6. Wilde MI, Wagstaff AJ: Acamprosate. A review of its pharmacology and clinical potential in the management of alcohol dependence after detoxification. Drugs. 1997 Jun;53(6):1038-53. Pubmed
External Links
ResourceLink
KEGG DrugD02780
PubChem Compound71158
PubChem Substance46506657
ChemSpider64300
ChEBI51041
ChEMBLCHEMBL1201293
Therapeutic Targets DatabaseDAP000857
PharmGKBPA10344
RxListhttp://www.rxlist.com/cgi/generic3/campral.htm
Drugs.comhttp://www.drugs.com/cdi/acamprosate.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cam1691.shtml
WikipediaAcamprosate
ATC CodesN07BB03
AHFS Codes
  • 28:92
PDB EntriesNot Available
FDA labelshow(815 KB)
MSDSNot Available
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

Targets

1. GABA-A receptor (anion channel)

Kind: protein group

Organism: Human

Pharmacological action: yes

Actions: positive modulator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-1 P14867 Details
Gamma-aminobutyric acid receptor subunit alpha-2 P47869 Details
Gamma-aminobutyric acid receptor subunit alpha-3 P34903 Details
Gamma-aminobutyric acid receptor subunit alpha-4 P48169 Details
Gamma-aminobutyric acid receptor subunit alpha-5 P31644 Details
Gamma-aminobutyric acid receptor subunit alpha-6 Q16445 Details
Gamma-aminobutyric acid receptor subunit beta-1 P18505 Details
Gamma-aminobutyric acid receptor subunit beta-2 P47870 Details
Gamma-aminobutyric acid receptor subunit beta-3 P28472 Details
Gamma-aminobutyric acid receptor subunit delta O14764 Details
Gamma-aminobutyric acid receptor subunit epsilon P78334 Details
Gamma-aminobutyric acid receptor subunit gamma-1 Q8N1C3 Details
Gamma-aminobutyric acid receptor subunit gamma-2 P18507 Details
Gamma-aminobutyric acid receptor subunit gamma-3 Q99928 Details
Gamma-aminobutyric acid receptor subunit pi O00591 Details
Gamma-aminobutyric acid receptor subunit theta Q9UN88 Details

References:

  1. Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80. Pubmed

2. Glutamate (NMDA) receptor

Kind: protein group

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 1 Q05586 Details
Glutamate receptor ionotropic, NMDA 2A Q12879 Details
Glutamate receptor ionotropic, NMDA 2B Q13224 Details
Glutamate receptor ionotropic, NMDA 2C Q14957 Details
Glutamate receptor ionotropic, NMDA 2D O15399 Details
Glutamate receptor ionotropic, NMDA 3A Q8TCU5 Details
Glutamate receptor ionotropic, NMDA 3B O60391 Details

References:

  1. Mann K, Kiefer F, Spanagel R, Littleton J: Acamprosate: recent findings and future research directions. Alcohol Clin Exp Res. 2008 Jul;32(7):1105-10. doi: 10.1111/j.1530-0277.2008.00690.×. Pubmed
  2. Witkiewitz K, Saville K, Hamreus K: Acamprosate for treatment of alcohol dependence: mechanisms, efficacy, and clinical utility. Ther Clin Risk Manag. 2012;8:45-53. doi: 10.2147/TCRM.S23184. Epub 2012 Feb 1. Pubmed
  3. Mann K, Kiefer F, Spanagel R, Littleton J: Acamprosate: recent findings and future research directions. Alcohol Clin Exp Res. 2008 Jul;32(7):1105-10. doi: 10.1111/j.1530-0277.2008.00690.×. Pubmed

3. Metabotropic glutamate receptor 5

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Metabotropic glutamate receptor 5 P41594 Details

References:

  1. De Witte P, Littleton J, Parot P, Koob G: Neuroprotective and abstinence-promoting effects of acamprosate: elucidating the mechanism of action. CNS Drugs. 2005;19(6):517-37. Pubmed

Transporters

1. Proton-coupled amino acid transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Proton-coupled amino acid transporter 1 Q7Z2H8 Details

References:

  1. Thwaites DT, Basterfield L, McCleave PM, Carter SM, Simmons NL: Gamma-Aminobutyric acid (GABA) transport across human intestinal epithelial (Caco-2) cell monolayers. Br J Pharmacol. 2000 Feb;129(3):457-64. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on December 02, 2013 15:50