Loprazolam

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
Thumb
Weight
Average: 464.904
Monoisotopic: 464.136366275
Chemical Formula
C23H21ClN6O3
Synonyms
  • Loprazolam
  • Triazulenone
External IDs
  • RU-31158 FREE BASE

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AGABA(A) Receptor
positive allosteric modulator
Humans
UGABA(A) Receptor Benzodiazepine Binding Site
ligand
Humans
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
Adverseeffects
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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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Loprazolam.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Loprazolam.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Loprazolam.
AclidiniumLoprazolam may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Loprazolam.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Loprazolam.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Loprazolam.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Loprazolam.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Loprazolam.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Loprazolam.
Interactions
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Food Interactions
Not Available

Categories

ATC Codes
N05CD11 — Loprazolam
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 / 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[8.4.0.0²,⁶]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
PubChem Compound
3033860
PubChem Substance
347829308
ChemSpider
2298440
RxNav
38555
ChEBI
135754
ChEMBL
CHEMBL2107448
ZINC
ZINC000022010289
Wikipedia
Loprazolam

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.0917 mg/mLALOGPS
logP2.8ALOGPS
logP2.68ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)19.13ChemAxon
pKa (Strongest Basic)8.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area97.33 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity126.87 m3·mol-1ChemAxon
Polarizability48.07 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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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
  1. 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]
  2. 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
  1. 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]
  2. 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 on June 23, 2017 20:45 / Updated on February 21, 2021 18:54