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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
Structure of NORDAZEPAM

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)

HIDE SMILES / InChI

Molecular Formula C15H11ClN2O
Molecular Weight 270.714
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Madar

PubMed

Sample Use Guides

In Vivo Use Guide
7.5-15 mg daily in the evening.
Route of Administration: Oral
In Vitro Use Guide
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
Record UNII
67220MCM01
Record Status Validated (UNII)
Record Version