Loprazolam

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Loprazolam
Accession Number
DB13643
Type
Small Molecule
Groups
Experimental
Description

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.

Structure
Thumb
Synonyms
  • Triazulenone
External IDs
RU-31158 FREE BASE
Categories
UNII
759N8462G8
CAS number
61197-73-7
Weight
Average: 464.904
Monoisotopic: 464.136366275
Chemical Formula
C23H21ClN6O3
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Loprazolam is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe therapeutic efficacy of Loprazolam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Loprazolam.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Loprazolam.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Loprazolam.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Loprazolam is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe therapeutic efficacy of Loprazolam can be decreased when used in combination with 6-O-benzylguanine.
7-DeazaguanineThe therapeutic efficacy of Loprazolam can be decreased when used in combination with 7-Deazaguanine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Loprazolam.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Loprazolam.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
3033860
PubChem Substance
347829308
ChemSpider
2298440
ChEBI
135754
ChEMBL
CHEMBL2107448
Wikipedia
Loprazolam
ATC Codes
N05CD11 — Loprazolam

Clinical Trials

Clinical Trials
Not Available

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

Taxonomy

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 / Alpha-amino acid or derivatives / Nitroaromatic compound / N-methylpiperazine / N-alkylpiperazine / Halobenzene / Chlorobenzene / Piperazine / Aryl chloride / Imidazolinone
show 35 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on June 23, 2017 14:45 / Updated on November 02, 2018 07:43