Identification
- Summary
Acamprosate is a medication used to maintain alcohol abstinence in patients with alcohol dependence.
- Brand Names
- Campral
- Generic Name
- Acamprosate
- DrugBank Accession Number
- DB00659
- Background
Alcohol use disorder is responsible for a large worldwide burden of morbidity, premature mortality, and economic consequences resulting from accidents, violence, incarceration, decreased productivity, and increased healthcare spending.8
Acamprosate, also known by the brand name Campral, is a drug used for the maintenance of alcohol abstinence. It is a structural analogue of the neurotransmitter γ-aminobutyric acid (GABA).12 Acamprosate is the first medication specifically formulated for the maintenance of alcohol abstinence in ethanol-dependent patients after alcohol detoxification4, unlike naltrexone and disulfiram. It was first approved by the FDA in 2004 and initially marketed by Forest Laboratories.13
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Acamprosate (DB00659)
- Weight
- Average: 181.21
Monoisotopic: 181.040878535 - Chemical Formula
- C5H11NO4S
- Synonyms
- 3-Acetamido-1-propanesulfonic acid
- Acamprosate
- Acamprosato
- Acamprosatum
- N-acetyl homotaurine
- N-Acetylhomotaurine
Pharmacology
- Indication
Acamprosate is indicated for the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation. It is also indicated for the maintenance of alcohol abstinence in patients who have undergone alcohol detoxification. This drug should be used with a psychosocial support program providing adequate support.11
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Maintenance of Alcohol abstinence •••••••••••• •• • •••••••••••• ••••••• ••••••• ••••••• ••••••• ••••••• Management of Alcohol dependence •••••••••••• •• • •••••••••••• ••••••• ••••••• ••••••• ••••••• ••••••• - Contraindications & Blackbox Warnings
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Acamprosate acts on the CNS, aiding in the restoration of normal glutaminergic neuron activity.1 Pharmacodynamic studies have shown that acamprosate calcium reduces alcohol intake in alcohol-dependent individuals, likely through effects on NMDA receptors and calcium channels.7 It is a safe and well-tolerated drug for patients with alcohol dependency and improves the likelihood of alcohol abstinence.1,12
- Mechanism of action
The mechanism of action of acamprosate for the maintenance of alcohol abstinence has not been established. Chronic alcohol exposure is believed to modify the balance between neuronal excitation and inhibition. Results of studies in animals suggest acamprosate may interact with glutamate and GABA neurotransmitter systems in the CNS, supporting the hypothesis that acamprosate restores the balance between neuronal excitation and inhibition.3,11 Evidence shows that acamprosate directly binds and inhibits GABA B receptors and indirectly affects GABA A receptors.5,10
Target Actions Organism AGlutamate (NMDA) receptor antagonistHumans AMetabotropic glutamate receptor 5 antagonistHumans AGamma-aminobutyric acid type B receptor subunit 1 inhibitorHumans - Absorption
Acamprosate is absorbed in the gastrointestinal tract. 5,6 The absolute bioavailability of acamprosate after oral administration is about 11%. The effect of food absorption is clinically insignificant and no adjustment of the dose is necessary with regard to meals.11 After repeated oral doses of 666 mg 3 times a day, steady-state concentrations are achieved within 5 to 7 days, with plasma concentration ranging between 370 to 650 micrograms/L.6
- Volume of distribution
At steady state concentrations, the distribution of acamprosate is about 20L.6 Following intravenous administration, the volume of distribution is about 72-109 L (an estimated 1 L/kg).11
- Protein binding
Acamprosate is not protein bound.6 Prescribing information mentions that acamprosate protein binding is negligible.11
- Metabolism
- Route of elimination
Half of acamprosate excretion occurs as unchanged acetyl-homotaurine in urine, and the other half possibly by biliary excretion.6 The kidneys are primarily responsible for the elimination of acamprosate.11
- Half-life
In pharmacokinetic studies, enteric-coated acamprosate tablets demonstrate a terminal elimination half-life 10-fold higher than reported 3 hour half-life after intravenous infusion of acamprosate.6 After two oral doses of acamprosate 333mg, the terminal half-life ranges between 20 - 33 hours.11
- Clearance
Severe renal insufficiency decreases the elimination of acamprosate, and is a contraindication.5,6 An acamprosate dose of 333mg, three times daily, is recommended for moderate renal impairment (creatinine clearance of 30-50 mL/min).11
- Adverse Effects
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The intraperitoneal LD50 in male mice is 1.87 g/kg.14 In reported cases of acute overdosage with acamprosate (doses of up to 56 grams of acamprosate calcium) diarrhea was the only reported symptom attributable to acamprosate. In the case of an overdose, supportive and symptomatic treatment is recommended.11
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetylsalicylic acid The excretion of Acamprosate can be decreased when combined with Acetylsalicylic acid. Acyclovir The excretion of Acamprosate can be decreased when combined with Acyclovir. Aminohippuric acid The excretion of Acamprosate can be decreased when combined with Aminohippuric acid. Apalutamide The excretion of Acamprosate can be decreased when combined with Apalutamide. Ataluren The excretion of Acamprosate can be decreased when combined with Ataluren. - Food Interactions
- Take with or without food. Food decreases drug absorption, but not to a clinically significant extent.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Acamprosate calcium 59375N1D0U 77337-73-6 BUVGWDNTAWHSKI-UHFFFAOYSA-L - Product Images
- International/Other Brands
- Regtect (Nippon Shinyaku Co., Ltd.)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acamprosate Calcium Tablet, coated 333 mg/1 Oral Forest Laboratories 2005-01-11 2015-05-31 US 
Campral Tablet, delayed release 333 mg/1 Oral Carilion Materials Management 2005-01-11 Not applicable US Campral Tablet, delayed release 333 mg/1 Oral Physicians Total Care, Inc. 2005-05-12 2011-06-30 US Campral Tablet, delayed release 333 mg Oral Mylan Pharmaceuticals 2007-07-30 Not applicable Canada 
Campral Tablet, delayed release 333 mg/1 Oral Forest Laboratories 2005-01-11 2016-02-29 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Avera McKennan Hospital 2015-08-17 2017-05-24 US 
Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Zydus Lifesciences Limited 2017-06-01 Not applicable US Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Zydus Pharmaceuticals (USA) Inc. 2017-06-01 Not applicable US Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral AvKARE 2016-05-16 Not applicable US 
Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Glenmark Pharmaceuticals Inc., USA 2013-07-16 Not applicable US
Categories
- ATC Codes
- N07BB03 — Acamprosate
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as organosulfonic acids. These are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Organic sulfonic acids and derivatives
- Sub Class
- Organosulfonic acids and derivatives
- Direct Parent
- Organosulfonic acids
- Alternative Parents
- Sulfonyls / Alkanesulfonic acids / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Alkanesulfonic acid / Carboximidic acid / Carboximidic acid derivative / Hydrocarbon derivative / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- organosulfonic acid, acetamides (CHEBI:51041)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- N4K14YGM3J
- CAS number
- 77337-76-9
- InChI Key
- 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
References
- Synthesis Reference
Claudia Cavarischia, Alex Comely, Marta Écijab, Tommaso Iacoangelia, Mireia Pastób, Lavinia Silvestria, Guido Furlotti. A Convenient, Scalable Process for the Preparation and Purification of Calcium Acamprosate. Synthesis. May 2020 DOI: 10.1055/s-0040-1707399
- General References
- Mason BJ: Treatment of alcohol-dependent outpatients with acamprosate: a clinical review. J Clin Psychiatry. 2001;62 Suppl 20:42-8. [Article]
- 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. [Article]
- Tsai G, Coyle JT: The role of glutamatergic neurotransmission in the pathophysiology of alcoholism. Annu Rev Med. 1998;49:173-84. [Article]
- 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. [Article]
- Kalk NJ, Lingford-Hughes AR: The clinical pharmacology of acamprosate. Br J Clin Pharmacol. 2014 Feb;77(2):315-23. doi: 10.1111/bcp.12070. [Article]
- Saivin S, Hulot T, Chabac S, Potgieter A, Durbin P, Houin G: Clinical pharmacokinetics of acamprosate. Clin Pharmacokinet. 1998 Nov;35(5):331-45. doi: 10.2165/00003088-199835050-00001. [Article]
- al Qatari M, Bouchenafa O, Littleton J: Mechanism of action of acamprosate. Part II. Ethanol dependence modifies effects of acamprosate on NMDA receptor binding in membranes from rat cerebral cortex. Alcohol Clin Exp Res. 1998 Jun;22(4):810-4. [Article]
- Kelly JF, Humphreys K, Ferri M: Alcoholics Anonymous and other 12-step programs for alcohol use disorder. Cochrane Database Syst Rev. 2020 Mar 11;3:CD012880. doi: 10.1002/14651858.CD012880.pub2. [Article]
- Wright TM, Myrick H: Acamprosate: a new tool in the battle against alcohol dependence. Neuropsychiatr Dis Treat. 2006 Dec;2(4):445-53. doi: 10.2147/nedt.2006.2.4.445. [Article]
- Berton F, Francesconi WG, Madamba SG, Zieglgansberger W, Siggins GR: Acamprosate enhances N-methyl-D-apartate receptor-mediated neurotransmission but inhibits presynaptic GABA(B) receptors in nucleus accumbens neurons. Alcohol Clin Exp Res. 1998 Feb;22(1):183-91. [Article]
- FDA Approved Drug Products: CAMPRAL (acamprosate calcium) delayed-release tablets [Link]
- AAFP: Acamprosate (Campral) for Treatment of Alcoholism [Link]
- NIH Online Books: Incorporating Alcohol Pharmacotherapies Into Medical Practice, Chapter 2 - Acamprosate [Link]
- Chemical book: Acamprosate chemical properties [Link]
- DailyMed: Acamprosate calcium delayed release tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0014797
- KEGG Drug
- D07058
- PubChem Compound
- 71158
- PubChem Substance
- 46506657
- ChemSpider
- 64300
- 82819
- ChEBI
- 51041
- ChEMBL
- CHEMBL1201293
- ZINC
- ZINC000001554588
- Therapeutic Targets Database
- DAP000857
- PharmGKB
- PA10344
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Acamprosate
- FDA label
- Download (815 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Alcohol Abuse / Alcohol Dependency / Major Depressive Disorder (MDD) 1 4 Completed Treatment Alcohol Dependency 5 4 Completed Treatment Alcohol Dependency / Bipolar Disorder (BD) 1 4 Completed Treatment Alcohol Dependency / Generalized Anxiety Disorder / Major Depressive Disorder (MDD) / Social Anxiety Disorder (SAD) 1 4 Completed Treatment Alcohol Use Disorders (AUD) 1
Pharmacoeconomics
- Manufacturers
- Forest laboratories inc
- Packagers
- Forest Pharmaceuticals
- Merck KGaA
- Murfreesboro Pharmaceutical Nursing Supply
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Tablet, coated Oral 333 mg/1 Tablet, coated Oral 333 MG Tablet, delayed release Oral 333 mg/1 Tablet, delayed release Oral 333 mg Tablet, film coated Oral 333 mg - Prices
Unit description Cost Unit Campral 333 mg Enteric Coated Tabs 0.98USD tab Campral 333 mg dose pak 0.95USD each Campral dr 333 mg tablet 0.95USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) >300 https://www.chemicalbook.com/ChemicalProductProperty_US_CB4310705.aspx water solubility >5mg/mL https://www.chemicalbook.com/ChemicalProductProperty_US_CB4310705.aspx logP -1.8 http://www.t3db.ca/toxins/T3D2853 logS -0.98 http://www.t3db.ca/toxins/T3D2853 pKa -1.1 http://www.t3db.ca/toxins/T3D2853 - Predicted Properties
Property Value Source Water Solubility 18.8 mg/mL ALOGPS logP -1.8 ALOGPS logP -2.8 Chemaxon logS -0.98 ALOGPS pKa (Strongest Acidic) -0.88 Chemaxon pKa (Strongest Basic) -1.5 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 83.47 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 38.91 m3·mol-1 Chemaxon Polarizability 17.17 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.8857 CYP450 2D6 inhibitor Non-inhibitor 0.9267 CYP450 2C19 inhibitor Non-inhibitor 0.8726 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 139.4597452 predictedDarkChem Lite v0.1.0 [M-H]- 139.2651452 predictedDarkChem Lite v0.1.0 [M-H]- 139.3100452 predictedDarkChem Lite v0.1.0 [M-H]- 130.91306 predictedDeepCCS 1.0 (2019) [M+H]+ 139.9893452 predictedDarkChem Lite v0.1.0 [M+H]+ 139.3149452 predictedDarkChem Lite v0.1.0 [M+H]+ 139.5853452 predictedDarkChem Lite v0.1.0 [M+H]+ 134.74228 predictedDeepCCS 1.0 (2019) [M+Na]+ 139.2919452 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.2264452 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.2035452 predictedDarkChem Lite v0.1.0 [M+Na]+ 143.57414 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein group
- Organism
- Humans
- 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 p...
Components:
References
- 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. [Article]
- 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. [Article]
- Kalk NJ, Lingford-Hughes AR: The clinical pharmacology of acamprosate. Br J Clin Pharmacol. 2014 Feb;77(2):315-23. doi: 10.1111/bcp.12070. [Article]
- Allgaier C, Franke H, Sobottka H, Scheibler P: Acamprosate inhibits Ca2+ influx mediated by NMDA receptors and voltage-sensitive Ca2+ channels in cultured rat mesencephalic neurones. Naunyn Schmiedebergs Arch Pharmacol. 2000 Nov;362(4-5):440-3. doi: 10.1007/s002100000285. [Article]
- Kind
- Protein
- Organism
- Humans
- 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...
- Gene Name
- GRM5
- Uniprot ID
- P41594
- Uniprot Name
- Metabotropic glutamate receptor 5
- Molecular Weight
- 132467.635 Da
References
- 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. [Article]
- Blednov YA, Harris RA: Metabotropic glutamate receptor 5 (mGluR5) regulation of ethanol sedation, dependence and consumption: relationship to acamprosate actions. Int J Neuropsychopharmacol. 2008 Sep;11(6):775-93. doi: 10.1017/S1461145708008584. Epub 2008 Apr 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- G-protein coupled gaba receptor activity
- Specific Function
- Component of a heterodimeric G-protein coupled receptor for GABA, formed by GABBR1 and GABBR2. Within the heterodimeric GABA receptor, only GABBR1 seems to bind agonists, while GABBR2 mediates coup...
- Gene Name
- GABBR1
- Uniprot ID
- Q9UBS5
- Uniprot Name
- Gamma-aminobutyric acid type B receptor subunit 1
- Molecular Weight
- 108319.4 Da
References
- Kalk NJ, Lingford-Hughes AR: The clinical pharmacology of acamprosate. Br J Clin Pharmacol. 2014 Feb;77(2):315-23. doi: 10.1111/bcp.12070. [Article]
- Berton F, Francesconi WG, Madamba SG, Zieglgansberger W, Siggins GR: Acamprosate enhances N-methyl-D-apartate receptor-mediated neurotransmission but inhibits presynaptic GABA(B) receptors in nucleus accumbens neurons. Alcohol Clin Exp Res. 1998 Feb;22(1):183-91. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Antonescu IE, Karlgren M, Pedersen ML, Simoff I, Bergstrom CAS, Neuhoff S, Artursson P, Steffansen B, Nielsen CU: Acamprosate Is a Substrate of the Human Organic Anion Transporter (OAT) 1 without OAT3 Inhibitory Properties: Implications for Renal Acamprosate Secretion and Drug-Drug Interactions. Pharmaceutics. 2020 Apr 24;12(4). pii: pharmaceutics12040390. doi: 10.3390/pharmaceutics12040390. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55