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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyAcamprosate
Identification
- Name
- Acamprosate
- Accession Number
- DB00659 (APRD00661)
- Type
- Small Molecule
- Groups
- Approved, 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
Structure for Acamprosate (DB00659)
- Synonyms
- 3-Acetamido-1-propanesulfonic acid
- Acamprosate
- Acamprosato
- Acamprosatum
- N-acetyl homotaurine
- N-Acetylhomotaurine
- Product Ingredients
Ingredient UNII CAS InChI Key Acamprosate calcium 59375N1D0U 77337-73-6 BUVGWDNTAWHSKI-UHFFFAOYSA-L - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End 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 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 Campral Tablet, delayed release 333 mg/1 Oral Physicians Total Care, Inc. 2005-05-12 2011-06-30 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Amerincan Health Packaging 2015-09-24 Not applicable US Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Avera McKennan Hospital 2015-08-17 2018-05-25 US 
Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Mylan Institutional Inc. 2013-07-16 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 Mylan Pharmaceuticals Inc. 2014-09-24 Not applicable US Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Cadila Pharnmaceuticals 2017-06-01 Not applicable US Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Glenmark Pharmaceuticals Inc., USA 2013-07-16 Not applicable US Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Marlex Pharmaceuticals Inc 2016-08-01 Not applicable US Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral Teva Pharmaceuticals USA, Inc. 2016-03-25 Not applicable US 
Acamprosate Calcium Tablet, delayed release 333 mg/1 Oral AvKARE, Inc. 2016-05-16 Not applicable US 
- International/Other Brands
- Regtect (Nippon Shinyaku Co., Ltd.)
- Categories
- UNII
- N4K14YGM3J
- CAS number
- 77337-76-9
- Weight
- Average: 181.21
Monoisotopic: 181.040878535 - Chemical Formula
- C5H11NO4S
- 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
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Pharmacology
- Indication
For the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation
- Associated Conditions
- Pharmacodynamics
Pharmacodynamic 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 action
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.
Target Actions Organism AGABA-A receptor (anion channel) positive modulatorHumans AGlutamate (NMDA) receptor antagonistHumans AMetabotropic glutamate receptor 5 antagonistHumans - Absorption
The 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 binding
Non detectable
- Metabolism
Acamprosate 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
- Clearance
- Not Available
- Toxicity
In 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
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- No interactions found.
- Food Interactions
- Take without regard to meals.
- Taking the product with food reduces its Cmax by 42% and total drug exposure by 23% (not considered significant).
References
- General References
- Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80. [PubMed:16300039]
- Mason BJ: Treatment of alcohol-dependent outpatients with acamprosate: a clinical review. J Clin Psychiatry. 2001;62 Suppl 20:42-8. [PubMed:11584875]
- 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]
- 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]
- Tsai G, Coyle JT: The role of glutamatergic neurotransmission in the pathophysiology of alcoholism. Annu Rev Med. 1998;49:173-84. [PubMed:9509257]
- 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
- Human Metabolome Database
- HMDB0014797
- KEGG Drug
- D07058
- PubChem Compound
- 71158
- PubChem Substance
- 46506657
- ChemSpider
- 64300
- ChEBI
- 51041
- ChEMBL
- CHEMBL1201293
- Therapeutic Targets Database
- DAP000857
- PharmGKB
- PA10344
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Acamprosate
- ATC Codes
- N07BB03 — Acamprosate
- AHFS Codes
- 28:92.00 — Miscellaneous Central Nervous System Agents
- FDA label
- Download (815 KB)
Clinical Trials
- Clinical Trials
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, delayed release Oral 333 mg Tablet, delayed release Oral 333 mg/1 - 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 logP -1.1 Not Available - 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) -1.1 ChemAxon pKa (Strongest Basic) -0.47 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
Taxonomy
- 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
- 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
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- organosulfonic acid, acetamides (CHEBI:51041)
Targets
- Kind
- Protein group
- Organism
- Humans
- 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...
Components:
References
- Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80. [PubMed:16300039]
- 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. [PubMed:18540918]
- 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
- 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. [PubMed:15963001]
Transporters
- Kind
- Protein
- Organism
- Humans
- 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 recog...
- Gene Name
- SLC36A1
- Uniprot ID
- Q7Z2H8
- Uniprot Name
- Proton-coupled amino acid transporter 1
- Molecular Weight
- 53075.045 Da
References
- 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]
Drug created on June 13, 2005 07:24 / Updated on April 21, 2019 05:29