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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
3-Acetamido-1-propanesulfonic acid
Acamprosato
Acamprosatum
N-acetyl homotaurine
N-Acetylhomotaurine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Campraltablet, delayed release333 mg/1oralForest Laboratories, Inc.2005-01-112016-02-29Us
Campraltablet (delayed-release)333 mgoralMylan Pharmaceuticals Ulc2007-07-30Not applicableCanada
Campraltablet, delayed release333 mg/1oralCarilion Materials Management2005-01-11Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acamprosate Calciumtablet, delayed release333 mg/1oralMylan Pharmaceuticals Inc.2014-09-24Not applicableUs
Acamprosate Calciumtablet, delayed release333 mg/1oralTeva Pharmaceuticals USA Inc2016-03-25Not applicableUs
Acamprosate Calciumtablet, delayed release333 mg/1oralAvera Mc Kennan Hospital2015-08-17Not applicableUs
Acamprosate Calciumtablet, delayed release333 mg/1oralGlenmark Pharmaceuticals Inc., Usa2013-07-16Not applicableUs
Acamprosate Calciumtablet, delayed release333 mg/1oralAmerican Health Packaging2015-10-01Not applicableUs
Acamprosate Calciumtablet, delayed release333 mg/1oralMylan Institutional Inc.2014-10-22Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
RegtectNippon Shinyaku Co., Ltd.
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Acamprosate Calcium
77337-73-6
Thumb
  • InChI Key:
  • Monoisotopic Mass:
  • Average Mass:
DBSALT000002Edit
Categories
UNIIN4K14YGM3J
CAS number77337-76-9
WeightAverage: 181.21
Monoisotopic: 181.040878535
Chemical FormulaC5H11NO4S
InChI KeyInChIKey=AFCGFAGUEYAMAO-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sulfonic acids. These 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
ClassSulfonic acids and derivatives
Sub ClassSulfonic acids
Direct ParentSulfonic acids
Alternative Parents
Substituents
  • Acetamide
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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.
Related Articles
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
PropertyValueProbability
Human Intestinal Absorption+0.5669
Blood Brain Barrier+0.9764
Caco-2 permeable-0.6797
P-glycoprotein substrateNon-substrate0.6973
P-glycoprotein inhibitor INon-inhibitor0.9056
P-glycoprotein inhibitor IINon-inhibitor0.9783
Renal organic cation transporterNon-inhibitor0.8969
CYP450 2C9 substrateNon-substrate0.7676
CYP450 2D6 substrateNon-substrate0.8124
CYP450 3A4 substrateNon-substrate0.5906
CYP450 1A2 substrateNon-inhibitor0.877
CYP450 2C9 inhibitorNon-inhibitor0.8857
CYP450 2D6 inhibitorNon-inhibitor0.9267
CYP450 2C19 inhibitorNon-inhibitor0.8726
CYP450 3A4 inhibitorNon-inhibitor0.9806
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9614
Ames testNon AMES toxic0.7031
CarcinogenicityNon-carcinogens0.5213
BiodegradationReady biodegradable0.6698
Rat acute toxicity1.9578 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9006
hERG inhibition (predictor II)Non-inhibitor0.878
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Forest laboratories inc
Packagers
Dosage forms
FormRouteStrength
Tablet, delayed releaseoral333 mg/1
Tablet (delayed-release)oral333 mg
Prices
Unit descriptionCostUnit
Campral 333 mg Enteric Coated Tabs0.98USD tab
Campral 333 mg dose pak0.95USD each
Campral dr 333 mg tablet0.95USD tablet
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 Solubility18.8 mg/mLALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80. [PubMed:16300039 ]
  2. Mason BJ: Treatment of alcohol-dependent outpatients with acamprosate: a clinical review. J Clin Psychiatry. 2001;62 Suppl 20:42-8. [PubMed:11584875 ]
  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:16546214 ]
  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:16467406 ]
  5. Tsai G, Coyle JT: The role of glutamatergic neurotransmission in the pathophysiology of alcoholism. Annu Rev Med. 1998;49:173-84. [PubMed:9509257 ]
  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:9179530 ]
External Links
ATC CodesN07BB03
AHFS Codes
  • 28:92
PDB EntriesNot Available
FDA labelDownload (815 KB)
MSDSNot Available
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

Kind
Protein group
Organism
Human
Pharmacological action
yes
Actions
positive modulator
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Components:
NameUniProt IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1P14867 Details
Gamma-aminobutyric acid receptor subunit alpha-2P47869 Details
Gamma-aminobutyric acid receptor subunit alpha-3P34903 Details
Gamma-aminobutyric acid receptor subunit alpha-4P48169 Details
Gamma-aminobutyric acid receptor subunit alpha-5P31644 Details
Gamma-aminobutyric acid receptor subunit alpha-6Q16445 Details
Gamma-aminobutyric acid receptor subunit beta-1P18505 Details
Gamma-aminobutyric acid receptor subunit beta-2P47870 Details
Gamma-aminobutyric acid receptor subunit beta-3P28472 Details
Gamma-aminobutyric acid receptor subunit deltaO14764 Details
Gamma-aminobutyric acid receptor subunit epsilonP78334 Details
Gamma-aminobutyric acid receptor subunit gamma-1Q8N1C3 Details
Gamma-aminobutyric acid receptor subunit gamma-2P18507 Details
Gamma-aminobutyric acid receptor subunit gamma-3Q99928 Details
Gamma-aminobutyric acid receptor subunit piO00591 Details
Gamma-aminobutyric acid receptor subunit thetaQ9UN88 Details
References
  1. Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80. [PubMed:16300039 ]
Kind
Protein group
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Voltage-gated cation channel activity
Specific Function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic plasticity, synaptogenesis, excitotoxicity, memory acquisition and learning. It mediates neuronal functions in glutamate neurotransmission. Is involved in the cell surface targeting of NMDA receptors (By similarity).
Components:
NameUniProt IDDetails
Glutamate receptor ionotropic, NMDA 1Q05586 Details
Glutamate receptor ionotropic, NMDA 2AQ12879 Details
Glutamate receptor ionotropic, NMDA 2BQ13224 Details
Glutamate receptor ionotropic, NMDA 2CQ14957 Details
Glutamate receptor ionotropic, NMDA 2DO15399 Details
Glutamate receptor ionotropic, NMDA 3AQ8TCU5 Details
Glutamate receptor ionotropic, NMDA 3BO60391 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.x. [PubMed:18540918 ]
  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:22346357 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Glutamate receptor activity
Specific Function:
G-protein coupled receptor for glutamate. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Signaling activates a phosphatidylinositol-calcium second messenger system and generates a calcium-activated chloride current. Plays an important role in the regulation of synaptic ...
Gene Name:
GRM5
Uniprot ID:
P41594
Molecular Weight:
132467.635 Da
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:15963001 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
L-proline transmembrane transporter activity
Specific Function:
Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid (By similarity).
Gene Name:
SLC36A1
Uniprot ID:
Q7Z2H8
Molecular Weight:
53075.045 Da
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:10711343 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23