U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H11ClN2O
Molecular Weight 270.7141
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORDAZEPAM

SMILES

c1ccc(cc1)C2=NCC(=Nc3ccc(cc32)Cl)O

InChI

InChIKey=AKPLHCDWDRPJGD-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C15H11ClN2O
Molecular Weight 270.7141
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including https://www.drugs.com/international/nordazepam.html | https://www.ncbi.nlm.nih.gov/pubmed/25099802 | https://goo.gl/QtLiQA | https://www.drugbank.ca/metabolites/DBMET00113

Nordazepam (INN; marketed under brand names Nordaz, Stilny, Madar, Vegesan, and Calmday) is a 1,4-benzodiazepine derivative with amnesic, anticonvulsant, anxiolytic, muscle relaxant, and sedative properties. Nordazepam is an active metabolite of diazepam, chlordiazepoxide, clorazepate, prazepam, pinazepam, and medazepam, used primarily in the treatment of anxiety disorders. Nordazepam is a partial agonist at the GABAA receptor, which makes it less potent than other benzodiazepines, particularly in its amnesic and muscle-relaxing effects. Nordazepam’s elimination half-life is between 36 and 200 hours, with wide variation among individuals; factors such as age and gender are known to impact it. The variation of reported half-life are attributed to differences in nordazepam metabolism and that of its metabolites as nordazepam is hydroxylated to active metabolites such as oxazepam, before finally being glucuronidated and excreted in the urine. Common side effects of nordazepam include somnolence, which is more common in elderly patients and/or people on high-dose regimens. Hypotonia, which is much less common, is also associated with high doses and/or old age.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Madar

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Microbiological degradation of diazepam.
1975
N-desmethyldiazepam physical dependence in dogs.
1985 Nov
Direct LC analysis of five benzodiazepines in human urine and plasma using an ADS restricted access extraction column.
2001 Dec
Binding of [3H]CB 34, a selective ligand for peripheral benzodiazepine receptors, to rat brain membranes.
2001 Dec 7
The simultaneous determination of diazepam and its three metabolites in dog plasma by high-performance liquid chromatography with mass spectroscopy detection.
2001 Sep
Sensitive method for the detection of 22 benzodiazepines by gas chromatography-ion trap tandem mass spectrometry.
2002 Apr 19
Quantitation using GC-TOF-MS: example of bromazepam.
2002 Aug 14
Fatal accident caused by isoflurane abuse.
2002 Dec
Determination of delorazepam in urine by solid-phase microextraction coupled to high performance liquid chromatography.
2002 Jun 1
Direct determination of benzodiazepines in biological fluids by restricted-access solid-phase microextraction.
2002 Mar 1
[Fatal outcome of poisoning with the benzodiazepines flunitrazepam and diazepam].
2002 Mar-Apr
Ximelagatran, an oral direct thrombin inhibitor, has a low potential for cytochrome P450-mediated drug-drug interactions.
2003
Effects of diazepam and its metabolites on nocturnal melatonin secretion in the rat pineal and Harderian glands. A comparative in vivo and in vitro study.
2003 Mar
Buprenorphine in drug-facilitated sexual abuse: a fatal case involving a 14-year-old boy.
2003 Oct
Screening, library-assisted identification and validated quantification of 23 benzodiazepines, flumazenil, zaleplone, zolpidem and zopiclone in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.
2004 Aug
Distribution of diazepam and nordiazepam between plasma and whole blood and the influence of hematocrit.
2004 Aug
Combined sedation with oral chlordemethyldiazepam and midazolam by nasal route in third molar surgery.
2004 May
High concentrations of diazepam and nordiazepam in blood of impaired drivers: association with age, gender and spectrum of other drugs present.
2004 Nov 10
Date-rape drugs scene in Poland.
2005
Development and validation of a liquid chromatographic/electrospray ionization mass spectrometric method for the quantitation of prazepam and its main metabolites in human plasma.
2005 Apr
Optimized determination of lorazepam in human serum by extraction and high-performance liquid chromatographic analysis.
2006 Dec
Liquid chromatographic-electrospray ionization mass spectrometric quantitative analysis of buprenorphine, norbuprenorphine, nordiazepam and oxazepam in rat plasma.
2006 Jun 16
LC-MS-MS analysis of 2,4-dinitrophenol and its phase I and II metabolites in a case of fatal poisoning.
2007 Jan-Feb
New high-performance liquid chromatographic method for serum analysis of oxazepam: application to bioequivalence and pharmacokinetic study.
2007 Jul-Aug
Fatal intoxication with labetalol (Trandate).
2008 Jul 4
Quantification of chlordesmethyldiazepam by liquid chromatography-tandem mass spectrometry: application to a cloxazolam bioequivalence study.
2009 Dec
Simultaneous analysis of diazepam and its metabolites in rat plasma and brain tissue by HPLC-UV and SPE.
2009 Nov 15
[Mechanisms of opioid-induced overdose: experimental approach to clinical concerns].
2009 Sep
Simultaneous determination and quantification of 12 benzodiazepines in serum or whole blood using UPLC/MS/MS.
2010
Quantitation of benzodiazepines in blood and urine using gas chromatography-mass spectrometry (GC-MS).
2010
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Effects of organic solvents on the time-dependent inhibition of CYP3A4 by diazepam.
2010 Jan
Measurement of benzodiazepines in urine by liquid chromatography-tandem mass spectrometry: confirmation of samples screened by immunoassay.
2010 Mar
Patents

Sample Use Guides

7.5-15 mg daily in the evening.
Route of Administration: Oral
Cryopreserved rat hepatocytes were thawed at 37°C for 1.5 min and centrifuged through supplemented Dulbecco’s modified Eagle’s medium containing Percoll for 5 min at 90g. The supernatant was removed and hepatocytes were washed by centrifugation in Dulbecco’s modified Eagle’s medium for 3 min at 60g. The pellet was resuspended in Waymouth MB 752/1 medium (Sigma Chemical) containing 5% FCS, and viability was assessed by trypan blue exclusion. The average viability of cryopreserved hepatocytes was 84.9 _ 3.8%. The cell suspension was diluted to the relevant cell density in Waymouth’s medium containing 5% FCS based on the number of viable cells and transferred (0.125 ml) into each well of a 24-well plate (Corning Glassworks, Corning, NY). All incubations were performed in an incubator (Sanyo Gallenkamp PLC, Leicester, UK) set at 37°C with 5% CO2 and _95% humidity. After 5-min preincubation, reactions were initiated by addition of 0.125 ml of prewarmed Waymouth’s medium containing 5% FCS and 1.25 _l of substrate in DMF followed by mixing for 10 s at 400 rpm. The final incubation volume was 0.25 ml and solvent concentration was 0.5% (v/v) in all incubations.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:50:59 UTC 2021
Edited
by admin
on Fri Jun 25 20:50:59 UTC 2021
Record UNII
67220MCM01
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORDAZEPAM
INN   MART.   MI   WHO-DD  
INN  
Official Name English
DESMETHYLDIAZEPAM
Common Name English
NORDIAZEPAM
Common Name English
DIAZEPAM IMPURITY A [EP]
Common Name English
RO 5-2180
Code English
N-DESMETHYLDIAZEPAM
Common Name English
NSC-46078
Code English
PRAXADIUM
Common Name English
MADAR
Brand Name English
7-CHLORO-1,3-DIHYDRO-5-PHENYL-2H-1,4-BENZODIAZEPIN-2-ONE
Systematic Name English
NORDAZEPAM [MART.]
Common Name English
NORDAZEPAM CIV
USP-RS  
Common Name English
CALMDAY
Brand Name English
NORDAZEPAM [INN]
Common Name English
NSC-631619
Code English
NORDAZEPAM [MI]
Common Name English
NORDAZEPAM [WHO-DD]
Common Name English
NORDAZEPAM CIV [USP-RS]
Common Name English
DEMADAR
Brand Name English
Classification Tree Code System Code
WHO-ATC N05BA16
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
WHO-VATC QN05BA16
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
NCI_THESAURUS C1012
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
DEA NO. 2838
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
Code System Code Type Description
RXCUI
3155
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY RxNorm
EPA CompTox
1088-11-5
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
FDA UNII
67220MCM01
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
PUBCHEM
2997
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
DRUG BANK
DB14028
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
CAS
1088-11-5
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
WIKIPEDIA
NORDAZEPAM
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
MERCK INDEX
M8050
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY Merck Index
MESH
D003708
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
214-123-4
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
DRUG CENTRAL
816
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
USP_CATALOG
1468400
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY USP-RS
EVMPD
SUB09358MIG
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
NCI_THESAURUS
C87675
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL523
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
INN
4400
Created by admin on Fri Jun 25 20:50:59 UTC 2021 , Edited by admin on Fri Jun 25 20:50:59 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
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METABOLITE -> PARENT
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PARENT -> IMPURITY
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