<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3089</id>
  <title>T3D3047</title>
  <common-name>Flunitrazepam</common-name>
  <description>A benzodiazepine with pharmacologic actions similar to those of diazepam that can cause anterograde amnesia. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug. [PubChem]</description>
  <cas>1622-62-4</cas>
  <pubchem-id>3380</pubchem-id>
  <chemical-formula>C16H12FN3O3</chemical-formula>
  <weight>313.086270</weight>
  <appearance>White powder.</appearance>
  <melting-point>166-167°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>8.58e-03 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>50% (suppository) and 64-77% (oral)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.</mechanism-of-toxicity>
  <metabolism>Hepatic.Half Life: 18-26 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For short-term treatment of severe insomnias, that are not responsive to other hypnotics. Not approved by the FDA in the U.S. In the U.K. it is used (and available only by private prescription) in some hospitals to sedate patients undergoing colonoscopy. In Norway, flunitrazepam is available as a prescription drug to treat insomnia under the brand name Flunipam 1 mg. [Wikipedia]</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>Symptoms of overdose include confusion, coma, impaired coordination, sleepiness, and slowed reaction time.</symptoms>
  <treatment>General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended.</treatment>
  <created-at type="dateTime">2009-07-21T20:28:51Z</created-at>
  <updated-at type="dateTime">2026-05-14T17:08:00Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Flunitrazepam</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>111715</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Flunitrazepam</stitch-id>
  <drugbank-id>DB01544</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>CN1C2=C(C=C(C=C2)[N+]([O-])=O)C(=NCC1=O)C1=CC=CC=C1F</moldb-smiles>
  <moldb-formula>C16H12FN3O3</moldb-formula>
  <moldb-inchi>InChI=1S/C16H12FN3O3/c1-19-14-7-6-10(20(22)23)8-12(14)16(18-9-15(19)21)11-4-2-3-5-13(11)17/h2-8H,9H2,1H3</moldb-inchi>
  <moldb-inchikey>PPTYJKAXVCCBDU-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">313.2832</moldb-average-mass>
  <moldb-mono-mass type="decimal">313.08626947</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.06</logp>
  <hmdb-id>HMDB15510</hmdb-id>
  <chembl-id>CHEMBL13280</chembl-id>
  <chemspider-id>3263</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;Kariss, J. and Newmark, H.L.; U.S. Patent 3,116,203; December 31, 1963; assigned to Hoffmann-la Roche Inc.  Kariss, J. and Newmark, H.L.; US. Patent 3,123,529; March 3,1964; assigned to Hoffmann-La Roche Inc.  Keiler, O., Steiger, N. and Sternbach, L.H.; U.S. Patent 3,203,990; August 31, 1965; assigned to Hoffmann-La Roche Inc.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002395</chemdb-id>
  <dsstox-id>DTXSID7023065</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00007996</susdat-id>
  <iupac>5-(2-fluorophenyl)-1-methyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one</iupac>
  <moldb-polar-surface-area>78.49000000000001</moldb-polar-surface-area>
  <moldb-refractivity>82.54820000000002</moldb-refractivity>
  <moldb-polarizability>29.601604891915457</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>1.6951775509848623</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>2.20</moldb-alogps-logp>
  <moldb-alogps-logs>-4.56</moldb-alogps-logs>
  <moldb-alogps-solubility>8.58e-03 g/l</moldb-alogps-solubility>
</compound>
