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<compound>
  <id type="integer">2895</id>
  <title>T3D2853</title>
  <common-name>Acamprosate</common-name>
  <description>Acamprosate belongs to the organosulfonic acids and derivatives, a subclass of organic sulfonic acids and derivatives within the organic compounds. This exogenous compound has the formula C5H11NO4S and an average molecular weight of 181.21 g/mol. At room temperature, it exists as a solid. Acamprosate is used as a drug and neurotransmitter agent (PMC3152312) and is a treatment for alcohol dependence (PMC3152312). It is recorded as being found in household cleaning and consumer products such as non electric simulated smoking devices, electrical and electronic equipment including radio transmission systems, and healthcare, pharmaceuticals and veterinary products specifically those used in addictive disorders. The recorded exposure route for this compound is oral.

The mechanism of action regarding the maintenance of alcohol abstinence is not completely understood, though chronic alcohol exposure is hypothesized to alter the normal balance between neuronal inhibition and excitation. Studies in vivo and in vitro in animals suggest acamprosate may interact centrally with GABA and glutamate neurotransmitter systems, leading to the hypothesis that the compound restores this balance. Acamprosate acts as an antagonist or inhibitor of Glutamate receptor ionotropic, NMDA 2D (GRIN2D), Glutamate receptor ionotropic, NMDA 3B (GRIN3B), Glutamate receptor ionotropic, NMDA 1 (GRIN1), Glutamate receptor ionotropic, NMDA 2A (GRIN2A), and three other proteins. Additionally, recorded protein targets include Metabotropic glutamate receptor 1 (GRM1), Metabotropic glutamate receptor 2 (GRM2), Metabotropic glutamate receptor 5 (GRM5), and Glutamate receptor ionotropic, NMDA 3A (GRIN3A).</description>
  <cas>77337-76-9</cas>
  <pubchem-id>71158</pubchem-id>
  <chemical-formula>C5H11NO4S</chemical-formula>
  <weight>181.040880</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1.88e+01 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>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.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>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. &lt;i&gt;in vitro&lt;/i&gt; and &lt;i&gt;in vivo&lt;/i&gt; 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.</mechanism-of-toxicity>
  <metabolism>Acamprosate does not undergo metabolism.Route of Elimination: Following oral administration of CAMPRAL&amp;#8482;, the major route of excretion is via the kidneys as acamprosate.Half Life: 20 - 33 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>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. </symptoms>
  <treatment>Treatment consists of discontinuation of Acamprosate together with appropriate symptomatic therapy. The judicious use of a cardioselective beta-receptor blocker may beconsidered, bearing in mind that such medication can produce bronchospasm. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:27:22Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:45:19Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Acamprosate</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>51041</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Acamprosate</stitch-id>
  <drugbank-id>DB00659</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC(=O)NCCCS(O)(=O)=O</moldb-smiles>
  <moldb-formula>C5H11NO4S</moldb-formula>
  <moldb-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)</moldb-inchi>
  <moldb-inchikey>AFCGFAGUEYAMAO-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">181.21</moldb-average-mass>
  <moldb-mono-mass type="decimal">181.040878535</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-1.1</logp>
  <hmdb-id>HMDB14797</hmdb-id>
  <chembl-id>CHEMBL1201293</chembl-id>
  <chemspider-id>64300</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002242</chemdb-id>
  <dsstox-id>DTXSID3044259</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00008367</susdat-id>
  <iupac>3-acetamidopropane-1-sulfonic acid</iupac>
  <moldb-polar-surface-area>83.47</moldb-polar-surface-area>
  <moldb-refractivity>38.9143</moldb-refractivity>
  <moldb-polarizability>17.165782807209713</moldb-polarizability>
  <moldb-rotatable-bond-count>4</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>-1.1448904008673297</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-0.46995019711612296</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-1</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>-1.79</moldb-alogps-logp>
  <moldb-alogps-logs>-0.98</moldb-alogps-logs>
  <moldb-alogps-solubility>1.88e+01 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organic acids and derivatives</superklass>
  <klass>Organic sulfonic acids and derivatives</klass>
  <subklass>Organosulfonic acids and derivatives</subklass>
  <paper-count type="integer">1151</paper-count>
  <sync-id>CED0004554</sync-id>
  <structure-inchikey>AFCGFAGUEYAMAO-UHFFFAOYSA-N</structure-inchikey>
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</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:00:37Z</structure-indexed-at>
</compound>
