This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Loprazolam
- DrugBank Accession Number
- DB13643
- Background
Loprazolam is an imidazobenzodiazepine with anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties. It is indicated for the short-term treatment of insomnia including difficulty in falling asleep and/or frequent nocturnal awakenings. Loprazolam is recommended as a short-term therapy only, due to adverse events associated with the drug including dependence and withdrawal symptoms. It is a positive modulator of GABA-A receptor that enhances the inhibitory neurotransmission. It is not an FDA-approved drug.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Loprazolam (DB13643)
- Weight
- Average: 464.904
Monoisotopic: 464.136366275 - Chemical Formula
- C23H21ClN6O3
- Synonyms
- Loprazolam
- Triazulenone
- External IDs
- RU-31158 FREE BASE
Pharmacology
- Indication
Not Available
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.- 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
Not Available
- Mechanism of action
Target Actions Organism AGABA(A) Receptor positive allosteric modulatorHumans UGABA(A) Receptor Benzodiazepine Binding Site ligandHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Loprazolam. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Loprazolam. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Loprazolam. Agomelatine The risk or severity of CNS depression can be increased when Agomelatine is combined with Loprazolam. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Loprazolam. - Food Interactions
- Not Available
Categories
- ATC Codes
- N05CD11 — Loprazolam
- Drug Categories
- Anti-Anxiety Agents
- Benzazepines
- Benzodiazepine hypnotics and sedatives
- Benzodiazepines and benzodiazepine derivatives
- Central Nervous System Agents
- Central Nervous System Depressants
- Heterocyclic Compounds, Fused-Ring
- Hypnotics and Sedatives
- Nervous System
- Psycholeptics
- Psychotropic Drugs
- Tranquilizing Agents
- 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 / Nitroaromatic compounds / Chlorobenzenes / N-methylpiperazines / Aryl chlorides / Imidazolinones / Vinylogous amides / Trialkylamines / Ketimines / Organic oxoazanium compounds show 10 more
- Substituents
- 1,4-benzodiazepine / 1,4-diazinane / 2-imidazoline / Allyl-type 1,3-dipolar organic compound / Alpha-amino acid or derivatives / Amidine / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl chloride show 35 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 759N8462G8
- CAS number
- 61197-73-7
- InChI Key
- UTEFBSAVJNEPTR-RGEXLXHISA-N
- 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-
- IUPAC Name
- (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
- SMILES
- [H]\C(N1CCN(C)CC1)=C1\N=C2CN=C(C3=CC=CC=C3Cl)C3=C(C=CC(=C3)N(=O)=O)N2C1=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 3033860
- PubChem Substance
- 347829308
- ChemSpider
- 2298440
- 38555
- ChEBI
- 135754
- ChEMBL
- CHEMBL2107448
- ZINC
- ZINC000022010289
- Wikipedia
- Loprazolam
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0917 mg/mL ALOGPS logP 2.8 ALOGPS logP 2.68 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 19.13 Chemaxon pKa (Strongest Basic) 7.66 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 97.33 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 126.87 m3·mol-1 Chemaxon Polarizability 47.92 Å3 Chemaxon Number of Rings 5 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
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 200.11711 predictedDeepCCS 1.0 (2019) [M+H]+ 202.51268 predictedDeepCCS 1.0 (2019) [M+Na]+ 208.42522 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
- Unknown
- 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 June 23, 2017 20:45 / Updated at February 21, 2021 18:54