<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2968</id>
  <title>T3D2926</title>
  <common-name>Tiagabine</common-name>
  <description>Tiagabine is an anti-convulsive medication. It is also used in the treatment for panic disorder as are a few other anticonvulsants. Though the exact mechanism by which tiagabine exerts its effect on the human body is unknown, it does appear to operate as a selective GABA reuptake inhibitor.</description>
  <cas>115103-54-3</cas>
  <pubchem-id>60648</pubchem-id>
  <chemical-formula>C20H25NO2S2</chemical-formula>
  <weight>375.132670</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>2.11e-02 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral. Tiagabine is nearly completely absorbed (&gt;95%).</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Though the exact mechanism by which Tiagabine exerts its effect on the human body is unknown, it does appear to operate as a selective GABA reuptake inhibitor.</mechanism-of-toxicity>
  <metabolism>Tiagabine is likely metabolized primarily by the 3A isoform subfamily of hepatic cytochrome P450.Route of Elimination: Approximately 2% of an oral dose of tiagabine is excreted unchanged, with 25% and 63% of the remaining dose excreted into the urine and feces, respectively, primarily as metabolites.Half Life: 7-9 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of partial seizures</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Respiratory depression was seen in a number of patients, including children, in the context of seizures. May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.</health-effects>
  <symptoms>Symptoms most often accompanying tiagabine overdose, alone or in combination with other drugs, have included: seizures including status epilepticus in patients with and without underlying seizure disorders, nonconvulsive status epilepticus, coma, ataxia, confusion, somnolence, drowsiness, impaired speech, agitation, lethargy, myoclonus, spike wave stupor, tremors, disorientation, vomiting, hostility, and temporary paralysis. Respiratory depression was seen in a number of patients, including children, in the context of seizures.</symptoms>
  <treatment>There is no specific antidote for overdose with Tiagabine. If indicated, elimination of unabsorbed drug should be achieved by emesis or  gastric lavage; usual precautions should be observed to maintain the airway. General supportive care of the patient is indicated including monitoring of  vital signs and observation of clinical status of the patient. Since tiagabine is mostly metabolized by the liver and is highly protein bound, dialysis is unlikely to be beneficial. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:27:55Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:53Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Tiagabine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07503</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>222170</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Tiagabine</stitch-id>
  <drugbank-id>DB00906</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>[H][C@]1(CCCN(CCC=C(C2=C(C)C=CS2)C2=C(C)C=CS2)C1)C(O)=O</moldb-smiles>
  <moldb-formula>C20H25NO2S2</moldb-formula>
  <moldb-inchi>InChI=1S/C20H25NO2S2/c1-14-7-11-24-18(14)17(19-15(2)8-12-25-19)6-4-10-21-9-3-5-16(13-21)20(22)23/h6-8,11-12,16H,3-5,9-10,13H2,1-2H3,(H,22,23)/t16-/m1/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=PBJUNZJWGZTSKL-MRXNPFEDSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">375.548</moldb-average-mass>
  <moldb-mono-mass type="decimal">375.132670429</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.6</logp>
  <hmdb-id>HMDB15042</hmdb-id>
  <chembl-id>CHEMBL1027</chembl-id>
  <chemspider-id>54661</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>&lt;p&gt;Henning Petersen, Peter Nielsen, Michael Cain, Subhash Patel, &amp;#8220;Crystalline Tiagabine monohydrate, its preparation and use.&amp;#8221; U.S. Patent US5354760, issued April, 1991.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
