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targets (5) transporters (1)
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Identification
Name Acamprosate
Accession Number DB00659 (APRD00661)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
3-(Acetylamino)propanesulphonic acid
3-Acetamido-1-propanesulfonic acid
N-Acetylhomotaurine
Salts Not Available
Brand names
Name Company
Campral
Brand mixtures Not Available
Categories
  • Alcohol Deterrents
CAS number 77337-76-9
Weight Average: 181.21
Monoisotopic: 181.040878535
Chemical Formula C5H11NO4S
InChI Key InChIKey=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)
Plain Text
IUPAC Name
3-acetamidopropane-1-sulfonic acid
SMILES
CC(=O)NCCCS(O)(=O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Sulfonic Acids and Derivatives
Substructures
  • Hydroxy Compounds
  • Amino Ketones
  • Sulfonyls
  • Carboxylic Acids and Derivatives
  • Sulfonic Acids and Derivatives
  • Carboxamides and Derivatives
Pharmacology
Indication For the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation
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.
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
Pharmacoeconomics
Manufacturers
  • Forest laboratories inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Campral 333 mg Enteric Coated Tabs 0.98 USD tab
Campral 333 mg dose pak 0.95 USD each
Campral dr 333 mg tablet 0.95 USD 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 1.88e+01 g/l 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 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 38.91 ChemAxon
polarizability 17.17 ChemAxon
References
Synthesis Reference Not 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
External Links
Resource Link
KEGG Drug D02780 Link_out
PubChem Compound 71158 Link_out
PubChem Substance 46506657 Link_out
ChemSpider 64300 Link_out
ChEBI 51041 Link_out
ChEMBL 51041 Link_out
Therapeutic Targets Database DAP000857 Link_out
PharmGKB PA10344 Link_out
RxList http://www.rxlist.com/cgi/generic3/campral.htm Link_out
Drugs.com http://www.drugs.com/cdi/acamprosate.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cam1691.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Acamprosate Link_out
ATC Codes
  • N07BB03
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (815 KB)
MSDS Not Available
Interactions
Drug Interactions Searched, but 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).
Targets

1. Glutamate [NMDA] receptor subunit 3A

Pharmacological action: yes
Actions: antagonist

NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism

Organism class: human
UniProt ID: Q8TCU5 Link_out
Gene: GRIN3A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Smothers CT, Woodward JJ: Pharmacological characterization of glycine-activated currents in HEK 293 cells expressing N-methyl-D-aspartate NR1 and NR3 subunits. J Pharmacol Exp Ther. 2007 Aug;322(2):739-48. Epub 2007 May 14. Pubmed

2. Metabotropic glutamate receptor 5

Pharmacological action: yes
Actions: antagonist

Receptor for glutamate. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol- calcium second messenger system and generates a calcium-activated chloride current

Organism class: human
UniProt ID: P41594 Link_out
Gene: GRM5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

3. Metabotropic glutamate receptor 1

Pharmacological action: unknown
Actions: antagonist

Receptor for glutamate. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol- calcium second messenger system. May participate in the central action of glutamate in the CNS, such as long-term potentiation in the hippocampus and long-term depression in the cerebellum

Organism class: human
UniProt ID: Q13255 Link_out
Gene: GRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. Metabotropic glutamate receptor 2

Pharmacological action: unknown
Actions: antagonist

Receptor for glutamate. The activity of this receptor is mediated by a G-protein that inhibits adenylate cyclase activity. May mediate suppression of neurotransmission or may be involved in synaptogenesis or synaptic stabilization

Organism class: human
UniProt ID: Q14416 Link_out
Gene: GRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Heilig M, Egli M: Pharmacological treatment of alcohol dependence: target symptoms and target mechanisms. Pharmacol Ther. 2006 Sep;111(3):855-76. Epub 2006 Mar 20. Pubmed

5. Metabotropic glutamate receptor 3

Pharmacological action: unknown
Actions: antagonist

Receptor for glutamate. The activity of this receptor is mediated by a G-protein that inhibits adenylate cyclase activity

Organism class: human
UniProt ID: Q14832 Link_out
Gene: GRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Transporters

1. Proton-coupled amino acid transporter 1

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

UniProt ID: Q7Z2H8 Link_out
Gene: SLC36A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19