<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2895</id>
  <title>T3D2853</title>
  <common-name>Acamprosate</common-name>
  <description>Acamprosate, also known by the brand name Campral&amp;trade;, 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.</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">2014-12-24T20:25:52Z</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>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"/>
</compound>
