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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:21 UTC
HMDB IDHMDB0014797
Secondary Accession Numbers
  • HMDB14797
Metabolite Identification
Common NameAcamprosate
DescriptionAcamprosate, 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
Data?1582753221
Synonyms
ValueSource
3-Acetamido-1-propanesulfonic acidChEBI
AcamprosatoChEBI
AcamprosatumChEBI
N-AcetylhomotaurineChEBI
AotalKegg
3-Acetamido-1-propanesulfonateGenerator
3-Acetamido-1-propanesulphonateGenerator
3-Acetamido-1-propanesulphonic acidGenerator
Acamprosic acidGenerator
3-(Acetylamino)propanesulphonic acidHMDB
CampralHMDB
Campral ecHMDB
N-Acetylhomotaurine, monopotassium saltHMDB
N-Acetylhomotaurine, zinc (2:1) saltHMDB
RegtectHMDB
Acamprosate calciumHMDB
N-Acetylhomotaurine, calcium (2:1) saltHMDB
N-Acetylhomotaurine, magnesium (2:1) saltHMDB
N-Acetylhomotaurine, monolithium saltHMDB
N-Acetylhomotaurine, monosodium saltHMDB
ZulexHMDB
Calcium acetyl homotaurinateHMDB
Calcium acetylhomotaurineHMDB
Sodium acetylhomotaurineHMDB
AOTAHMDB
AcamprostateHMDB
Calcium acetylhomotaurinateHMDB
Acetyl homotaurinate, calciumMeSH
Acetylhomotaurinate, calciumMeSH
N Acetylhomotaurine, monolithium saltMeSH
Acetylhomotaurine, calciumMeSH
Acetylhomotaurine, sodiumMeSH
N Acetylhomotaurine, monosodium saltMeSH
N AcetylhomotaurineMeSH
N Acetylhomotaurine, monopotassium saltMeSH
Chemical FormulaC5H11NO4S
Average Molecular Weight181.21
Monoisotopic Molecular Weight181.040878535
IUPAC Name3-acetamidopropane-1-sulfonic acid
Traditional Nameacamprosate
CAS Registry Number77337-76-9
SMILES
CC(=O)NCCCS(O)(=O)=O
InChI Identifier
InChI=1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)
InChI KeyAFCGFAGUEYAMAO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids 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
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
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
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.8 g/LNot Available
LogP-1.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility18.8 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.91 m³·mol⁻¹ChemAxon
Polarizability17.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-9100000000-8420bb56903c56b30a73Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-1900000000-095fc64fb4490a8d6b4dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-c177d5ee7162b0b8756dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-40eaa1bb480a68330940Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-1900000000-35bfe6cae36755d1cf1cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0059-9500000000-d366cda3213379d7501bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9000000000-4374601f59e1dc8df0ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9000000000-011f30e0257faffd4553Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-c179316d784a91f87c59Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-8cf123c7cf7dddcf6838Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-1900000000-84a7d1cc6ca5022d4da7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0059-9500000000-4503d9afc6bab741521bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9000000000-8c2ba21c044eeada7839Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9000000000-dd14c920c5211780d172Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-1900000000-dac38f625c8648b643c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-3684e08456a971400c3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-6137fe4463b3675f55ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-58f776a52000101b8fb7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0900000000-d8de420d40b45a34ea95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001l-0900000000-1bb28abe8034966ad829Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0900000000-343cd651472c88796a61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-5900000000-0c71e48c69c18769563dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-181e815cd85a7505ce4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-4900000000-1f6b18b2f30371ea12baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9500000000-50bd4d569514037edb1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-ec0629ff72c5e58a0413Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00659 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00659 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00659
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID64300
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcamprosate
METLIN IDNot Available
PubChem Compound71158
PDB IDNot Available
ChEBI ID51041
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tsai G, Coyle JT: The role of glutamatergic neurotransmission in the pathophysiology of alcoholism. Annu Rev Med. 1998;49:173-84. [PubMed:9509257 ]
  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. Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80. [PubMed:16300039 ]
  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. 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 ]

Enzymes

General function:
Involved in G-protein coupled receptor activity
Specific function:
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
Gene Name:
GRM5
Uniprot ID:
P41594
Molecular weight:
132467.6
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 ]
General function:
Involved in G-protein coupled receptor activity
Specific function:
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
Gene Name:
GRM1
Uniprot ID:
Q13255
Molecular weight:
132365.9
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:17139284 ]
  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:17016423 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
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
Gene Name:
GRIN3A
Uniprot ID:
Q8TCU5
Molecular weight:
125464.1
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:17502428 ]