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<compound>
  <id type="integer">4701</id>
  <title>T3D4647</title>
  <common-name>Loprazolam</common-name>
  <description>Loprazolam is an exogenous organic compound with the formula C23H21ClN6O3 and an average molecular weight of 464.90 g/mol. It exists as a solid at room temperature. Loprazolam belongs to the 1,4-benzodiazepines, a subclass of benzodiazepines within the organic compounds.

Marketed under the brand names Dormonoct, Havlane, Sonin, and Somnovit, this drug is an imidazole benzodiazepine derivative used for the short-term treatment of moderately severe insomnia. It is available in 2 mg and 1 mg tablets and possesses sedative, anxiolytic, anticonvulsant, and skeletal muscle relaxant properties.

The compound acts on 20 recorded protein targets, serving as a positive allosteric modulator of the Translocator protein (TSPO), Gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1), Gamma-aminobutyric acid receptor subunit alpha-2 (GABRA2), Gamma-aminobutyric acid receptor subunit alpha-3 (GABRA3), and 16 other proteins. Loprazolam has been found in or released from two recorded sources: Household cleaning &amp; consumer products (Non Electric Simulated Smoking Devices) and Electrical &amp; Electronic Equipment (Antennas).</description>
  <cas>61197-73-7</cas>
  <pubchem-id>3033860</pubchem-id>
  <chemical-formula>C23H21ClN6O3</chemical-formula>
  <weight>464.9</weight>
  <appearance>White powder.</appearance>
  <melting-point nil="true"/>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility nil="true"/>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <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 nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Loprazolam is licensed and marketed for the short term treatment of moderately severe insomnia.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <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">2014-09-08T02:40:14Z</created-at>
  <updated-at type="dateTime">2026-08-21T23:50:00Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id nil="true"/>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB13643</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H]\C(N1CCN(C)CC1)=C1\N=C2CN=C(C3=CC=CC=C3Cl)C3=C(C=CC(=C3)N(=O)=O)N2C1=O</moldb-smiles>
  <moldb-formula>C23H21ClN6O3</moldb-formula>
  <moldb-inchi>InChI=1S/C23H21ClN6O3/c1-27-8-10-28(11-9-27)14-19-23(31)29-20-7-6-15(30(32)33)12-17(20)22(25-13-21(29)26-19)16-4-2-3-5-18(16)24/h2-7,12,14H,8-11,13H2,1H3/b19-14-</moldb-inchi>
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  <moldb-average-mass type="decimal">464.904</moldb-average-mass>
  <moldb-mono-mass type="decimal">464.136366275</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.68</logp>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL2107448</chembl-id>
  <chemspider-id>2298440</chemspider-id>
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  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003605</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00015441</susdat-id>
  <iupac>(4Z)-9-(2-chlorophenyl)-4-[(4-methylpiperazin-1-yl)methylidene]-12-nitro-2,5,8-triazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),5,8,11,13-pentaen-3-one</iupac>
  <moldb-polar-surface-area>97.33000000000001</moldb-polar-surface-area>
  <moldb-refractivity>126.86799999999994</moldb-refractivity>
  <moldb-polarizability>48.068009644575405</moldb-polarizability>
  <moldb-rotatable-bond-count>3</moldb-rotatable-bond-count>
  <moldb-acceptor-count>7</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic>19.13464169919963</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>8.06004295325157</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>5</moldb-number-of-rings>
  <moldb-alogps-logp>2.80</moldb-alogps-logp>
  <moldb-alogps-logs>-3.71</moldb-alogps-logs>
  <moldb-alogps-solubility>9.17e-02 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organoheterocyclic compounds</superklass>
  <klass>Benzodiazepines</klass>
  <subklass>1,4-benzodiazepines</subklass>
  <paper-count type="integer">79</paper-count>
  <sync-id>CED0014591</sync-id>
  <structure-inchikey>UTEFBSAVJNEPTR-RGEXLXHISA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:01:25Z</structure-indexed-at>
</compound>
