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)
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 |
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Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7861419 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Madar Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Diazepam poisoning with one-month monitoring of diazepam and nordiazepam blood levels. | 2001 Jun |
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The simultaneous determination of diazepam and its three metabolites in dog plasma by high-performance liquid chromatography with mass spectroscopy detection. | 2001 Sep |
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Sensitive method for the detection of 22 benzodiazepines by gas chromatography-ion trap tandem mass spectrometry. | 2002 Apr 19 |
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SPME-LC with UV detection to study delorazepam-serum albumin interactions. | 2002 Jul 31 |
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Direct determination of benzodiazepines in biological fluids by restricted-access solid-phase microextraction. | 2002 Mar 1 |
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[Fatal outcome of poisoning with the benzodiazepines flunitrazepam and diazepam]. | 2002 Mar-Apr |
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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 |
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Coexistence and concentrations of ethanol and diazepam in postmortem blood specimens: risk for enhanced toxicity? | 2003 Nov |
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Toxicological data and growth characteristics of single post-feeding larvae and puparia of Calliphora vicina (Diptera: Calliphoridae) obtained from a controlled nordiazepam study. | 2004 Aug |
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High concentrations of diazepam and nordiazepam in blood of impaired drivers: association with age, gender and spectrum of other drugs present. | 2004 Nov 10 |
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Date-rape drugs scene in Poland. | 2005 |
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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 |
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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 |
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Fast in vivo microextraction: a new tool for clinical analysis. | 2006 Apr |
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Liquid chromatographic-electrospray ionization mass spectrometric quantitative analysis of buprenorphine, norbuprenorphine, nordiazepam and oxazepam in rat plasma. | 2006 Jun 16 |
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Quantification of benzodiazepines in whole blood and serum. | 2006 Nov |
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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 |
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Voriconazole and fluconazole increase the exposure to oral diazepam. | 2007 Oct |
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Bioavailability and dose proportionality of intramuscular diazepam administered by autoinjector. | 2008 Apr |
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Alleged breaches of "standards of medical care" in a patient overdose death possibly related to chronic opioid analgesic therapy, application of the controlled substances model guidelines: case report. | 2009 Apr |
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Quantification of chlordesmethyldiazepam by liquid chromatography-tandem mass spectrometry: application to a cloxazolam bioequivalence study. | 2009 Dec |
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Simultaneous determination and quantification of 12 benzodiazepines in serum or whole blood using UPLC/MS/MS. | 2010 |
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Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
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Effects of organic solvents on the time-dependent inhibition of CYP3A4 by diazepam. | 2010 Jan |
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Measurement of benzodiazepines in urine by liquid chromatography-tandem mass spectrometry: confirmation of samples screened by immunoassay. | 2010 Mar |
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.
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N05BA16
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QN05BA16
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NCI_THESAURUS |
C1012
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DEA NO. |
2838
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NORDAZEPAM
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
PARENT (METABOLITE ACTIVE)