Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H11ClN2O |
Molecular Weight | 270.714 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC2=C(NC(=O)CN=C2C3=CC=CC=C3)C=C1
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)
Molecular Formula | C15H11ClN2O |
Molecular Weight | 270.714 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28242100Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28242100
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7861419 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Madar Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Diazepam poisoning with one-month monitoring of diazepam and nordiazepam blood levels. | 2001 Jun |
|
A contemporaneous finding of fenproporex in a polydrug suicide. | 2001 Oct |
|
Quantitation using GC-TOF-MS: example of bromazepam. | 2002 Aug 14 |
|
Determination of delorazepam in urine by solid-phase microextraction coupled to high performance liquid chromatography. | 2002 Jun 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 |
|
Evaluation of the novel antiepileptic drug, AWD 131-138, for benzodiazepine-like discriminative stimulus and reinforcing effects in squirrel monkeys. | 2003 Apr 4 |
|
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 |
|
Date-rape drugs scene in Poland. | 2005 |
|
Hair analysis by liquid chromatography-tandem mass spectrometry in toxicological investigation of drug-facilitated crimes: report of 128 cases over the period June 2003-May 2004 in metropolitan Paris. | 2005 Oct 4 |
|
Fast in vivo microextraction: a new tool for clinical analysis. | 2006 Apr |
|
Highlights on new food research. | 2006 Dec |
|
Liquid chromatographic-electrospray ionization mass spectrometric quantitative analysis of buprenorphine, norbuprenorphine, nordiazepam and oxazepam in rat plasma. | 2006 Jun 16 |
|
A sensitive and selective method for the detection of diazepam and its main metabolites in urine by gas chromatography-tandem mass spectrometry. | 2007 Feb 2 |
|
LC-MS-MS analysis of 2,4-dinitrophenol and its phase I and II metabolites in a case of fatal poisoning. | 2007 Jan-Feb |
|
Medicolegal aspects of tetrazepam metabolism. | 2007 May |
|
Determination of diazepam and its metabolites in human urine by liquid chromatography/tandem mass spectrometry using a hydrophilic polymer column. | 2008 Aug |
|
Thiodicarb and methomyl tissue distribution in a fatal multiple compounds poisoning. | 2008 Mar |
|
Selection of adequate optimization criteria in chromatographic separations. | 2009 Jul |
|
LC-MS/MS analysis of 13 benzodiazepines and metabolites in urine, serum, plasma, and meconium. | 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 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15100178
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
Edited
Fri Dec 15 15:05:53 GMT 2023
by
admin
on
Fri Dec 15 15:05:53 GMT 2023
|
Record UNII |
67220MCM01
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
N05BA16
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
||
|
WHO-VATC |
QN05BA16
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
||
|
NCI_THESAURUS |
C1012
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
||
|
DEA NO. |
2838
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
111762
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
1468400
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
3155
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | RxNorm | ||
|
DTXSID2049000
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
100000090394
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
67220MCM01
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
2997
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
DB14028
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
1088-11-5
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
NORDAZEPAM
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
m8050
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | Merck Index | ||
|
D003708
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
214-123-4
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
816
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
46078
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
SUB09358MIG
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
C87675
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
CHEMBL523
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
4400
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY | |||
|
631619
Created by
admin on Fri Dec 15 15:05:53 GMT 2023 , Edited by admin on Fri Dec 15 15:05:53 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
BINDER->LIGAND |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT | |||
|
PARENT -> METABOLITE ACTIVE | |||
|
PARENT -> METABOLITE TOXIC |
Metabolite produces adverse autonomic nervous symptoms in man.
|
||
|
METABOLITE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |