Identification
- Summary
Lormetazepam is a benzodiazepine indicated in the treatment of anxiety and the induction of anesthesia.
- Generic Name
- Lormetazepam
- DrugBank Accession Number
- DB13872
- Background
Lormatazepam is an orally available benzodiazepine used in the UK for the treatment of short-term insomnia 2. It is marketed by Auden Mckenzie (Pharma Division) in 0.5 and 1 mg tablet formulations.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Lormetazepam (DB13872)
- Weight
- Average: 335.185
Monoisotopic: 334.027583052 - Chemical Formula
- C16H12Cl2N2O2
- Synonyms
- (±)-Lormetazepam
- (RS)-Lormetazepam
- 7-Chloro-1,3-dihydro-5-(o-chlorophenyl)-3-hydroxy-1-methyl-2H-1,4-benzodiazepin-2-one
- 7-Chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2H-1,4-benzodiazepin-2-one
- Lormetazepam
- Methyllorazepam
- N-Methyllorazepam
Pharmacology
- Indication
For the treatment of short-term insomnia 2
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Severe insomnia •••••••••••• ••••••• •••••• Symptomatic treatment of Sleep disorder •••••••••••• ••••• •••••••• • •••••• •••••• Symptomatic treatment of Acute anxiety •••••••••••• ••••• •••••••••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Lormetazepam is a benzodiazepine which reduces central nervous system (CNS) activity 2,1. It produces anxiolytic, muscle relaxant, sedative and hypnotic effects. Because it is a short-acting benzodiapine, it does not produce significant sedation after waking.
- Mechanism of action
Lormetazepam, as a benzodiazepine, binds to the regulatory site between the α and γ subunits of γ-aminobutryic acid (GABA) A receptors with γ2 and α1, α2, α3, or α5 subunits 1. This facilitates the opening of the chloride channel allowing chloride ions to flow into the neuron resulting in hyperpolarization. Hyperpolarized neurons require greater simulation to reach their action potential threshold. The general inhibitory effect on neuronal depolarization produces the effects of lormetazepam.
Target Actions Organism AGABA(A) Receptor positive allosteric modulatorHumans AGABA(A) Receptor Benzodiazepine Binding Site ligandHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Metabolised to an inactive metabolite via glucuronide conjugation 2
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- Route of elimination
Not Available
- Half-life
The terminal phase half life is 11 h 2.
- Clearance
Not Available
- Adverse Effects
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The primary manifestation of overdosage ranges from drowsiness to coma and symptoms may include ataxia, hypotension, hypotonia, respiratory depression which may lead to death 2.
Experimental LD50 values are as follows 3: Mouse - 780 mg/kg (intraperitoneal), 1790 mg/kg (oral), 10000 mg/kg (subcutaneous). Rat - 6250 mg/kg (intraperitoneal), 10000 mg/kg (oral), 10000 mg/kg (intraperitoneal).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when 1,2-Benzodiazepine is combined with Lormetazepam. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Lormetazepam. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Lormetazepam. Agomelatine The risk or severity of CNS depression can be increased when Agomelatine is combined with Lormetazepam. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Lormetazepam. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
Categories
- ATC Codes
- N05CD06 — Lormetazepam
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzodiazepines
- Sub Class
- 1,4-benzodiazepines
- Direct Parent
- 1,4-benzodiazepines
- Alternative Parents
- Alpha amino acids and derivatives / Chlorobenzenes / Aryl chlorides / Tertiary carboxylic acid amides / Lactams / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Alkanolamines / Organopnictogen compounds show 4 more
- Substituents
- 1,4-benzodiazepine / Alkanolamine / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxamide group show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organochlorine compound, 1,4-benzodiazepinone (CHEBI:52993)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- GU56C842ZA
- CAS number
- 848-75-9
- InChI Key
- FJIKWRGCXUCUIG-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H12Cl2N2O2/c1-20-13-7-6-9(17)8-11(13)14(19-15(21)16(20)22)10-4-2-3-5-12(10)18/h2-8,15,21H,1H3
- IUPAC Name
- 7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
- SMILES
- CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl
References
- General References
- 43. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 533-534). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
- MRHA: Lormetazepam Summary of Product Characteristics [Link]
- ChemIDPlus: Lormetazepam [Link]
- BASG: Sedalor (Lormetazepam) Intravenous Injection [Link]
- External Links
- Human Metabolome Database
- HMDB0041919
- PubChem Compound
- 13314
- PubChem Substance
- 347829324
- ChemSpider
- 12750
- 28894
- ChEBI
- 52993
- ChEMBL
- CHEMBL22097
- Wikipedia
- Lormetazepam
- MSDS
- Download (49.8 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Sedation in Intensive Care Unit Patients 1 3 Completed Treatment Sleep Initiation and Maintenance Disorders 1 3 Terminated Treatment Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia 1 3 Terminated Treatment Sleep Initiation and Maintenance Disorders 1 Not Available Completed Not Available Critically Ill Patients 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 1 mg Capsule Oral 1.0 MG Capsule Oral 2.0 MG Tablet Oral 0.5 MG Tablet Oral 1.0 MG Tablet Oral 2.0 MG Tablet, coated Solution / drops Oral Solution / drops Oral 2.5 MG/ML Tablet, coated 1 MG Tablet, coated 2 MG Tablet Oral Tablet Oral 2 MG Injection, solution Parenteral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0164 mg/mL ALOGPS logP 2.92 ALOGPS logP 3.39 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 10.68 Chemaxon pKa (Strongest Basic) -2.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 52.9 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 85.82 m3·mol-1 Chemaxon Polarizability 32.2 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 171.8920132 predictedDarkChem Lite v0.1.0 [M-H]- 167.01735 predictedDeepCCS 1.0 (2019) [M+H]+ 172.1928132 predictedDarkChem Lite v0.1.0 [M+H]+ 169.37535 predictedDeepCCS 1.0 (2019) [M+Na]+ 171.8618132 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.67409 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- Curator comments
- The GABA(A) receptor is pentameric (i.e. comprising 5 subunit proteins) and therefore has a multitude of potential isoforms. The above target is a collection of all possible GABA(A) subunits that may participate in the formation of the pentameric receptor and is not meant to imply direct a drug-protein interaction for each individual subunit.
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
- Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- Curator comments
- Benzodiazepines modulate GABA(A) function by binding at the interface between alpha (α) and gamma (γ) subunits. Of the 6 α-subunits, only 4 (α-1, -2, -3, and -5) participate in the formation of this binding site. The above target is a collection of all α- and γ-subunits that are known to participate in the formation of the benzodiazepine binding site.
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
- Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
Drug created at July 07, 2017 21:36 / Updated at May 21, 2021 10:23