<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2950</id>
  <title>T3D2908</title>
  <common-name>Progabide</common-name>
  <description>Progabide is an exogenous solid compound with the formula C17H16ClFN2O2 and an average molecular weight of 334.77 g/mol. Progabide belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds.

This compound acts on three protein targets: GABRA1, GABBR1, and GABBR2, for which it is an agonist. Progabide binds to both GABAA and GABAB receptors located on the terminals of primary afferent fibers. Binding to GABAA increases the affinity of the GABA receptor for the amino acid, augments the flux of chloride ions across the terminal membrane, and increases the amount of presynaptic inhibition. Activation of GABAB receptors retards the influx of calcium ions into the terminals, which reduces the evoked release of excitatory amino acids and possibly other transmitters.</description>
  <cas>62666-20-0</cas>
  <pubchem-id>5361323</pubchem-id>
  <chemical-formula>C17H16ClFN2O2</chemical-formula>
  <weight>334.088430</weight>
  <appearance>White powder.</appearance>
  <melting-point>133-135°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>70.9 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Well absorbed with a bioavailability of 60%</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Progabide binds to both GABA&lt;sub&gt;A&lt;/sub&gt; and GABA&lt;sub&gt;B&lt;/sub&gt; receptors located on the terminals of primary afferent fibers. Binding to GABA&lt;sub&gt;A&lt;/sub&gt; results in an increased affinity of the GABA receptor for the amino acid, an augmented flux of chloride ions across the terminal membrane, and an increase in the amount of presynaptic inhibition. Activation of the GABA&lt;sub&gt;B&lt;/sub&gt; receptors retards the influx of calcium ions into the terminals, thereby reducing the evoked release of excitatory amino acids and possibly other transmitters.</mechanism-of-toxicity>
  <metabolism>HepaticHalf Life: 4 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Indicated for the treatment of epilepsy.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.</health-effects>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:27:47Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:50:16Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Progabide</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Progabide</stitch-id>
  <drugbank-id>DB00837</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>NC(=O)CCCN\C(C1=CC=C(Cl)C=C1)=C1/C=C(F)C=CC1=O</moldb-smiles>
  <moldb-formula>C17H16ClFN2O2</moldb-formula>
  <moldb-inchi>InChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,21H,1-2,9H2,(H2,20,23)/b17-14+</moldb-inchi>
  <moldb-inchikey>DWEQWXSKOHHBNT-SAPNQHFASA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">334.773</moldb-average-mass>
  <moldb-mono-mass type="decimal">334.088433678</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>3.06</logp>
  <hmdb-id>HMDB14975</hmdb-id>
  <chembl-id>CHEMBL287631</chembl-id>
  <chemspider-id>4514729</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>CHEM002285</chemdb-id>
  <dsstox-id>DTXSID00878140</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00004318</susdat-id>
  <iupac>4-{[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino}butanimidic acid</iupac>
  <moldb-polar-surface-area>72.19</moldb-polar-surface-area>
  <moldb-refractivity>91.22189999999999</moldb-refractivity>
  <moldb-polarizability>33.20826964666348</moldb-polarizability>
  <moldb-rotatable-bond-count>6</moldb-rotatable-bond-count>
  <moldb-acceptor-count>3</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>15.315554078461773</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>4.014268264490627</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>2.68</moldb-alogps-logp>
  <moldb-alogps-logs>-4.88</moldb-alogps-logs>
  <moldb-alogps-solubility>4.42e-03 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organic oxygen compounds</superklass>
  <klass>Organooxygen compounds</klass>
  <subklass>Carbonyl compounds</subklass>
  <paper-count type="integer">251</paper-count>
  <sync-id>CED0014757</sync-id>
  <structure-inchikey>DWEQWXSKOHHBNT-SAPNQHFASA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:38Z</structure-indexed-at>
</compound>
