<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2749</id>
  <title>T3D2707</title>
  <common-name>Lorazepam</common-name>
  <description>Lorazepam is only found in individuals that have used or taken this drug. It is a benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent. [PubChem]Lorazepam binds to an allosteric site on GABA-A receptors, which are pentameric ionotropic receptors in the CNS. Binding potentiates the effects of the inhibitory neurotransmitter GABA, which upon binding opens the chloride channel in the receptor, allowing chloride influx and causing hyperpolerization of the neuron.</description>
  <cas>846-49-1</cas>
  <pubchem-id>3958</pubchem-id>
  <chemical-formula>C15H10Cl2N2O2</chemical-formula>
  <weight>320.011930</weight>
  <appearance>White powder.</appearance>
  <melting-point>192-194°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>80 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Parenteral (intravenous, sublingual); oral.Readily absorbed with an absolute bioavailability of 90% when given orally. When intramuscularly administered, lorazepam is completely and rapidly absorbed. It achieves max serum concentration in 3 hours. The max serum concentration of a 4 mg dose is 48 ng/mL. </route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Lorazepam binds to an allosteric site on GABA-A receptors, which are pentameric ionotropic receptors in the CNS. Binding potentiates the effects of the inhibitory neurotransmitter GABA, which upon binding opens the chloride channel in the receptor, allowing chloride influx and causing hyperpolerization of the neuron.</mechanism-of-toxicity>
  <metabolism>Lorazepam is hepatically metabolized and is extensively conjugated to the 3-0-phenolic glucuronide. This is an inactive metabolite and is eliminated mainly by the kidneys. Route of Elimination: When a single 2 mg oral dose is give to healthy subjects, 88&amp;#177;4% of the administered dose was recovered in urine and 7&amp;#177;2% was recovered in feces. The percent of administered dose recovered in urine as lorazepam glucuronide was 74&amp;#177;4%. Only 0.3% of the dose was recovered as unchanged lorazepam, and the remainder of the radioactivity represented minor metabolites.Half Life: Parenteral administration = 14&amp;#177;5 hours;Oral administration = 2 hours. </metabolism>
  <toxicity> LD50, mouse, oral = 1850 mg/kgLD50: 3178mg/kg (oral, mice)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the management of anxiety disorders, and for treatment of status epilepticus.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.</health-effects>
  <symptoms>Somnolence, confusion, and coma.</symptoms>
  <treatment>General supportive and symptomatic measures are recommended. Vital signs must be monitored and the patient closely observed. When there is a risk of aspiration, induction of emesis is not recommended. Gastric lavage may be indicated if performed soon after ingestion or in symptomatic patients. Administration of activated charcoal may also limit drug absorption. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:26:14Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:24:32Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Lorazepam</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>52993</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Lorazepam</stitch-id>
  <drugbank-id>DB00186</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>OC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(Cl)=C2</moldb-smiles>
  <moldb-formula>C15H10Cl2N2O2</moldb-formula>
  <moldb-inchi>InChI=1S/C15H10Cl2N2O2/c16-8-5-6-12-10(7-8)13(19-15(21)14(20)18-12)9-3-1-2-4-11(9)17/h1-7,15,21H,(H,18,20)</moldb-inchi>
  <moldb-inchikey>DIWRORZWFLOCLC-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">321.158</moldb-average-mass>
  <moldb-mono-mass type="decimal">320.011932988</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.39</logp>
  <hmdb-id>HMDB14332</hmdb-id>
  <chembl-id>CHEMBL580</chembl-id>
  <chemspider-id>3821</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;Igor Lifshitz, &amp;#8220;Process for preparing pure crystalline lorazepam.&amp;#8221; U.S. Patent US20010039340, issued November 08, 2001.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002139</chemdb-id>
  <dsstox-id>DTXSID7023225</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00000034</susdat-id>
  <iupac>7-chloro-5-(2-chlorophenyl)-3-hydroxy-2,3-dihydro-1H-1,4-benzodiazepin-2-one</iupac>
  <moldb-polar-surface-area>61.69</moldb-polar-surface-area>
  <moldb-refractivity>82.6992</moldb-refractivity>
  <moldb-polarizability>30.334841164498854</moldb-polarizability>
  <moldb-rotatable-bond-count>1</moldb-rotatable-bond-count>
  <moldb-acceptor-count>3</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>10.606301472079005</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-2.2363530659722866</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>2.98</moldb-alogps-logp>
  <moldb-alogps-logs>-4.26</moldb-alogps-logs>
  <moldb-alogps-solubility>1.76e-02 g/l</moldb-alogps-solubility>
</compound>
