Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2022-03-07 02:51:35 UTC |
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HMDB ID | HMDB0014332 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Lorazepam |
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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. |
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Structure | OC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(Cl)=C2 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) |
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Synonyms | Value | Source |
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Ativan | Kegg | (+/-)-lorazepam | HMDB | O-Chlorooxazepam | HMDB | O-Chloroxazepam | HMDB | AHP brand OF lorazepam | MeSH, HMDB | apo Lorazepam | MeSH, HMDB | Llorens brand OF lorazepam | MeSH, HMDB | Lorazepam ahp brand | MeSH, HMDB | Lorazepam baxter brand | MeSH, HMDB | Lorazepam medical | MeSH, HMDB | Lorazepam medix brand | MeSH, HMDB | Lorazepam wyeth brand | MeSH, HMDB | Lorazepam neuraxpharm brand | MeSH, HMDB | Lorazepam ratiopharm brand | MeSH, HMDB | Medix brand OF lorazepam | MeSH, HMDB | novo Lorazem | MeSH, HMDB | novo-Lorazem | MeSH, HMDB | Novopharm brand OF lorazepam | MeSH, HMDB | Lorazep von CT | MeSH, HMDB | Neuraxpharm brand OF lorazepam | MeSH, HMDB | Ratiopharm brand OF lorazepam | MeSH, HMDB | Dolorgiet brand OF lorazepam | MeSH, HMDB | Duralozam | MeSH, HMDB | Laubeel | MeSH, HMDB | Lorazepam apotex brand | MeSH, HMDB | Lorazepam desitin brand | MeSH, HMDB | Lorazepam CT-arzneimittel brand | MeSH, HMDB | Lorazepam-ratiopharm | MeSH, HMDB | Merck dura brand OF lorazepam | MeSH, HMDB | Nu-loraz | MeSH, HMDB | Riemser brand OF lorazepam | MeSH, HMDB | Serra pamies brand OF lorazepam | MeSH, HMDB | Sinestron | MeSH, HMDB | Temesta | MeSH, HMDB | Tolid | MeSH, HMDB | Wyeth, orfidal | MeSH, HMDB | CT Arzneimittel brand OF lorazepam | MeSH, HMDB | ApoLorazepam | MeSH, HMDB | Baxter brand OF lorazepam | MeSH, HMDB | Idalprem | MeSH, HMDB | Lorazepam dolorgiet brand | MeSH, HMDB | Lorazepam medical brand | MeSH, HMDB | Lorazepam novartis brand | MeSH, HMDB | Lorazepam riemser brand | MeSH, HMDB | Lorazepam ratiopharm | MeSH, HMDB | Lorazepam-neuraxpharm | MeSH, HMDB | Medical brand OF lorazepam | MeSH, HMDB | Medical, lorazepam | MeSH, HMDB | NovoLorazem | MeSH, HMDB | Nu loraz | MeSH, HMDB | Orfidal wyeth | MeSH, HMDB | Somagerol | MeSH, HMDB | apo-Lorazepam | MeSH, HMDB | Apotex brand OF lorazepam | MeSH, HMDB | Desitin brand OF lorazepam | MeSH, HMDB | Donix | MeSH, HMDB | Durazolam | MeSH, HMDB | Lorazepam llorens brand | MeSH, HMDB | Lorazepam novopharm brand | MeSH, HMDB | Lorazepam nu-pharm brand | MeSH, HMDB | Lorazepam neuraxpharm | MeSH, HMDB | Novartis brand OF lorazepam | MeSH, HMDB | Nu pharm brand OF lorazepam | MeSH, HMDB | Nu-pharm brand OF lorazepam | MeSH, HMDB | NuLoraz | MeSH, HMDB | Sedicepan | MeSH, HMDB | Wyeth brand OF lorazepam | MeSH, HMDB | CT-Arzneimittel brand OF lorazepam | MeSH, HMDB | Von CT, lorazep | MeSH, HMDB |
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Chemical Formula | C15H10Cl2N2O2 |
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Average Molecular Weight | 321.158 |
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Monoisotopic Molecular Weight | 320.011932988 |
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IUPAC Name | 7-chloro-5-(2-chlorophenyl)-3-hydroxy-2,3-dihydro-1H-1,4-benzodiazepin-2-one |
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Traditional Name | lorazepam |
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CAS Registry Number | 846-49-1 |
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SMILES | OC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(Cl)=C2 |
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InChI Identifier | 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) |
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InChI Key | DIWRORZWFLOCLC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzodiazepines |
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Sub Class | 1,4-benzodiazepines |
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Direct Parent | 1,4-benzodiazepines |
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Alternative Parents | |
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Substituents | - 1,4-benzodiazepine
- Alpha-amino acid or derivatives
- Chlorobenzene
- Halobenzene
- Aryl chloride
- Aryl halide
- Monocyclic benzene moiety
- Benzenoid
- Carboxamide group
- Ketimine
- Secondary carboxylic acid amide
- Lactam
- Alkanolamine
- Carboxylic acid derivative
- Azacycle
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Imine
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organohalogen compound
- Organochloride
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 166 - 168 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.018 g/L | Not Available | LogP | 3.5 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross SectionsAdduct Type | Data Source | CCS Value (Å2) | Reference |
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[M+H]+ | CBM | 165.8 | 30932474 |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Lorazepam,1TMS,isomer #1 | C[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C2NC1=O | 2753.9 | Semi standard non polar | 33892256 | Lorazepam,1TMS,isomer #2 | C[Si](C)(C)N1C(=O)C(O)N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C21 | 2571.4 | Semi standard non polar | 33892256 | Lorazepam,2TMS,isomer #1 | C[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C2N([Si](C)(C)C)C1=O | 2591.1 | Semi standard non polar | 33892256 | Lorazepam,2TMS,isomer #1 | C[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C2N([Si](C)(C)C)C1=O | 2612.5 | Standard non polar | 33892256 | Lorazepam,2TMS,isomer #1 | C[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C2N([Si](C)(C)C)C1=O | 3526.9 | Standard polar | 33892256 | Lorazepam,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C2NC1=O | 2909.3 | Semi standard non polar | 33892256 | Lorazepam,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)C(O)N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C21 | 2785.7 | Semi standard non polar | 33892256 | Lorazepam,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C2N([Si](C)(C)C(C)(C)C)C1=O | 2932.6 | Semi standard non polar | 33892256 | Lorazepam,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C2N([Si](C)(C)C(C)(C)C)C1=O | 3001.7 | Standard non polar | 33892256 | Lorazepam,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C2N([Si](C)(C)C(C)(C)C)C1=O | 3593.5 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Lorazepam EI-B (Non-derivatized) | splash10-009i-6791000000-942b7493f1e9fc3d12be | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lorazepam EI-B (Non-derivatized) | splash10-009i-6791000000-942b7493f1e9fc3d12be | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lorazepam GC-MS (Non-derivatized) - 70eV, Positive | splash10-004u-0290000000-b7b54d40e4a40249fc2d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lorazepam GC-MS (1 TMS) - 70eV, Positive | splash10-00b9-9235000000-97d74a04d7ec48e6bb28 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lorazepam GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lorazepam GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lorazepam GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lorazepam GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lorazepam GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-002r-4981000000-a567f7beb26ee18d061c | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-qTof , Positive-QTOF | splash10-00b9-0298000000-986499cda13643ef7d85 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , negative-QTOF | splash10-001i-0091000000-04730f82e569df7febdd | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , negative-QTOF | splash10-001i-0390000000-dd63d93f2fa81cbb5928 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , negative-QTOF | splash10-0udi-0930000000-3ecf1f2f10049a3cfee2 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , negative-QTOF | splash10-0udi-0910000000-95d23a9a121bf45ef8bf | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , negative-QTOF | splash10-0udi-0900000000-cdbe26e697f259770c28 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , negative-QTOF | splash10-0udi-0900000000-4046d54b4dd9bf7968be | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , negative-QTOF | splash10-001i-0091000000-abaf38ed3aa6e7d51245 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QTOF , positive-QTOF | splash10-052b-9000000000-dda683413448d0461123 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , positive-QTOF | splash10-00di-0009000000-53bbea620bd1e8b49eb3 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , positive-QTOF | splash10-0fb9-0095000000-793565a97e3afc2ce858 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , positive-QTOF | splash10-004i-0090000000-41097b8a64363c5e2f94 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , positive-QTOF | splash10-004i-0290000000-a0694111a3943eca2b53 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , positive-QTOF | splash10-004i-0690000000-5a4728cb7e2473fc6b3c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , positive-QTOF | splash10-01rf-0940000000-39d041fbab4fb67a5c41 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam , positive-QTOF | splash10-00b9-0298000000-986499cda13643ef7d85 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam LC-ESI-QFT , positive-QTOF | splash10-00b9-0196000000-2e53b39b27c66ec73fd2 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam 30V, Positive-QTOF | splash10-004i-0090000000-4b5b5c3dfb63873733bf | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lorazepam -1V, Positive-QTOF | splash10-052b-9000000000-dda683413448d0461123 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lorazepam 10V, Positive-QTOF | splash10-00di-0029000000-ee07ef7d365d458f9d34 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lorazepam 20V, Positive-QTOF | splash10-00di-0239000000-5c6908c1fea1275fb874 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lorazepam 40V, Positive-QTOF | splash10-0zfr-1981000000-3701b2aca45eeea63d62 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lorazepam 10V, Negative-QTOF | splash10-014i-0009000000-58ac02858c22990ff345 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lorazepam 20V, Negative-QTOF | splash10-014i-0339000000-f3e5eccf9c4e49dcfbcf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lorazepam 40V, Negative-QTOF | splash10-000i-3490000000-6b141b0755058109e70a | 2016-08-03 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00186 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00186 | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 3821 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | Not Available |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Heisterkamp DV, Cohen PJ: The effect of intravenous premedication with lorazepam (ativan), pentobarbitone or diazepam on recall. Br J Anaesth. 1975 Jan;47(1):79-81. [PubMed:238548 ]
- Milligan DW, Howard MR, Judd A: Premedication with lorazepam before bone marrow biopsy. J Clin Pathol. 1987 Jun;40(6):696-8. [PubMed:3611398 ]
- Lader M: Short-term versus long-term benzodiazepine therapy. Curr Med Res Opin. 1984;8 Suppl 4:120-6. [PubMed:6144459 ]
- Kemper N, Poser W, Poser S: [Benzodiazepine dependence: addiction potential of the benzodiazepines is greater than previously assumed (author's transl)]. Dtsch Med Wochenschr. 1980 Dec 5;105(49):1707-12. [PubMed:7439058 ]
- Maltais F, Laberge F, Laviolette M: A randomized, double-blind, placebo-controlled study of lorazepam as premedication for bronchoscopy. Chest. 1996 May;109(5):1195-8. [PubMed:8625666 ]
- (). FDA label . .
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