Nordazepam

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

Identification

Summary

Nordazepam is a benzodiazepine indicated in the treatment of insomnia.

Generic Name
Nordazepam
DrugBank Accession Number
DB14028
Background

An intermediate in the metabolism of DIAZEPAM to OXAZEPAM. It may have actions similar to those of diazepam.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 270.714
Monoisotopic: 270.055990691
Chemical Formula
C15H11ClN2O
Synonyms
  • Desmethyldiazepam
  • N-desmethyldiazepam
  • Nordazepam
  • Nordazepam CIV
  • Nordazepamum
  • Nordiazepam
External IDs
  • A 101
  • A101
  • RO 5-2180

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofSevere insomnia••••••••••••••••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AGABA(A) Receptor
positive allosteric modulator
Humans
AGABA(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
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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 CNS depression can be increased when 1,2-Benzodiazepine is combined with Nordazepam.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Nordazepam.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Nordazepam.
AgomelatineThe risk or severity of CNS depression can be increased when Agomelatine is combined with Nordazepam.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Nordazepam.
Food Interactions
Not Available

Products

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International/Other Brands
Calmday / Lomax / Madar / Sopax / Stilny / Vegesan

Categories

ATC Codes
N05BA16 — Nordazepam
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
Benzene and substituted derivatives / Aryl chlorides / Cyclic carboximidic acids / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
1,4-benzodiazepine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Cyclic carboximidic acid / Hydrocarbon derivative / Imine / Ketimine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, 1,4-benzodiazepinone (CHEBI:111762)
Affected organisms
Not Available

Chemical Identifiers

UNII
67220MCM01
CAS number
1088-11-5
InChI Key
AKPLHCDWDRPJGD-UHFFFAOYSA-N
InChI
InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)
IUPAC Name
7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
SMILES
ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1

References

General References
  1. AIFA: Madar (Nordazepam) Oral Tablet [Link]
Human Metabolome Database
HMDB0060538
KEGG Drug
D08283
KEGG Compound
C07486
ChemSpider
2890
BindingDB
50027835
RxNav
3155
ChEBI
111762
ChEMBL
CHEMBL523
ZINC
ZINC000001249069
Wikipedia
Nordazepam

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Pill
Tablet, coated
TabletOral15 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0219 mg/mLALOGPS
logP2.79ALOGPS
logP3.21Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.3Chemaxon
pKa (Strongest Basic)2.85Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area41.46 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity76.7 m3·mol-1Chemaxon
Polarizability27.41 Å3Chemaxon
Number of Rings3Chemaxon
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-06tf-0190000000-29b106f0dfb9b4601898
Mass Spectrum (Electron Ionization)MSsplash10-006x-1290000000-16289dee622e983dadb4
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-0090000000-08ab493d917dff556803
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0090000000-b3902adae33dd2ada996
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0090000000-e1f36555cb45aafb3578
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0090000000-4599707b6c514e2fd140
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0090000000-2afa9f8bad136457e913
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-052f-0090000000-39292916fbbd987c9c79
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0490000000-93d06070b3ddb4f2bb1d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0900000000-319db7de66dd214c6036
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-f12d8a37190a6a1a6260
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00dl-0590000000-6667f22f2eaaa4d7d444
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-05mo-0950000000-9f91849bf0ea300eddf6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-052f-0940000000-113f94a665f60922a3cc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0090000000-a17b063554f54d5ae790
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0090000000-00d132ae0ea246d26e2a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0390000000-02873020d1329d3d5c38
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-1960000000-010c3ba06f80d4ace994
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-052f-1930000000-327cc931b60592065b64
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-2910000000-0a0897ca546d1bc1cb27
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f6x-4900000000-7cc6b852b0d715a021c2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ufr-7900000000-d4ef23e43b78528b7c96
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0w4i-9700000000-9ef8e88327da379c2b33
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-81cb9a7a9e781ecb17de
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-6d5313d113ec73ad146c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-ab136a75d6b3fc8a48cd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-3090000000-dde4d1ce9f21623268e0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0o6v-1190000000-57a4a52270d5df1ea3c0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9010000000-209159060ca82d4ec31c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-ed8f4840543169e349b3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0159-5090000000-c95c398a65af4a36d6d0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-7ce007df0731bb17cb3b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-5090000000-ba6d2e998d0bf2b542a8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gwr-0490000000-c024848873bd0a9df8e8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-11b9d76ac8b55bc8639f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-163.002191
predicted
DarkChem Lite v0.1.0
[M-H]-161.6612
predicted
DeepCCS 1.0 (2019)
[M-H]-163.002191
predicted
DarkChem Lite v0.1.0
[M-H]-161.6612
predicted
DeepCCS 1.0 (2019)
[M+H]+163.316791
predicted
DarkChem Lite v0.1.0
[M+H]+164.01918
predicted
DeepCCS 1.0 (2019)
[M+H]+163.316791
predicted
DarkChem Lite v0.1.0
[M+H]+164.01918
predicted
DeepCCS 1.0 (2019)
[M+Na]+163.076391
predicted
DarkChem Lite v0.1.0
[M+Na]+170.11234
predicted
DeepCCS 1.0 (2019)
[M+Na]+163.076391
predicted
DarkChem Lite v0.1.0
[M+Na]+170.11234
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
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
  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 at May 15, 2018 20:27 / Updated at May 14, 2021 01:06