<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2846</id>
  <title>T3D2804</title>
  <common-name>Chlordiazepoxide</common-name>
  <description>Chlordiazepoxide is only found in individuals that have used or taken this drug. It is an anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal. Chlordiazepoxide binds to stereospecific benzodiazepine (BZD) binding sites on GABA (A) receptor complexes at several sites within the central nervous system, including the limbic system and reticular formation. This results in an increased binding of the inhibitory neurotransmitter GABA to the GABA(A) receptor.BZDs, therefore, enhance GABA-mediated chloride influx through GABA receptor channels, causing membrane hyperpolarization. The net neuro-inhibitory effects result in the observed sedative, hypnotic, anxiolytic, and muscle relaxant properties.</description>
  <cas>58-25-3</cas>
  <pubchem-id>2712</pubchem-id>
  <chemical-formula>C16H14ClN3O</chemical-formula>
  <weight>299.082540</weight>
  <appearance>White powder.</appearance>
  <melting-point>236-236.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>2000 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Chlordiazepoxide binds to stereospecific benzodiazepine (BZD) binding sites on GABA (A) receptor complexes at several sites within the central nervous system, including the limbic system and reticular formation. This results in an increased binding of the inhibitory neurotransmitter GABA to the GABA(A) receptor.BZDs, therefore, enhance GABA-mediated chloride influx through GABA receptor channels, causing membrane hyperpolarization. The net neuro-inhibitory effects result in the observed sedative, hypnotic, anxiolytic, and muscle relaxant properties.</mechanism-of-toxicity>
  <metabolism>Hepatic.Route of Elimination: Chlordiazepoxide is excreted in the urine, with 1% to 2% unchanged and 3% to 6% as conjugate.Half Life: 24-48 hours</metabolism>
  <toxicity>LD50: 537 mg/kg (Oral, Rat) (A308)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the management of anxiety disorders or for the short-term relief of symptoms of anxiety, withdrawal symptoms of acute alcoholism, and preoperative apprehension and anxiety.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.</health-effects>
  <symptoms>Signs of overdose include respiratory depression, muscle weakness, somnolence (general depressed activity).</symptoms>
  <treatment>General supportive measures should be employed, along with immediate gastric lavage. Intravenous fluids should be administered and an adequate airway maintained. Hypotension may be combated by the use of Levophed (norepinephrine) or Aramine (metaraminol). Flumazenil, a specific benzodiazepine-receptor antagonist, is indicated for the complete or partial reversal of the sedative effects of benzodiazepines and may be used in situations when an overdose with a benzodiazepine is known or suspected. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:27:00Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:51Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Chlordiazepoxide</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>3611</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Chlordiazepoxide</stitch-id>
  <drugbank-id>DB00475</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>CN=C1CN(=O)=C(C2=CC=CC=C2)C2=C(N1)C=CC(Cl)=C2</moldb-smiles>
  <moldb-formula>C16H14ClN3O</moldb-formula>
  <moldb-inchi>InChI=1S/C16H14ClN3O/c1-18-15-10-20(21)16(11-5-3-2-4-6-11)13-9-12(17)7-8-14(13)19-15/h2-9H,10H2,1H3,(H,18,19)</moldb-inchi>
  <moldb-inchikey>InChIKey=ANTSCNMPPGJYLG-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">299.755</moldb-average-mass>
  <moldb-mono-mass type="decimal">299.082539792</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.44</logp>
  <hmdb-id>HMDB14618</hmdb-id>
  <chembl-id>CHEMBL451</chembl-id>
  <chemspider-id>10248513</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;Sternbach, L.H.; US. Patent 2,893,992; July 7,1959; assigned to Hoffmann-LaRoche, Inc.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
