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

Details

Stereochemistry ACHIRAL
Molecular Formula C15H11N3O3
Molecular Weight 281.2661
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NITRAZEPAM

SMILES

[O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C3=CC=CC=C3)C=C1

InChI

InChIKey=KJONHKAYOJNZEC-UHFFFAOYSA-N
InChI=1S/C15H11N3O3/c19-14-9-16-15(10-4-2-1-3-5-10)12-8-11(18(20)21)6-7-13(12)17-14/h1-8H,9H2,(H,17,19)

HIDE SMILES / InChI

Molecular Formula C15H11N3O3
Molecular Weight 281.2661
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/mmx/nitrazepam.html | https://www.ncbi.nlm.nih.gov/pubmed/27685474 | https://www.ncbi.nlm.nih.gov/pubmed/12657414 | https://www.medicines.org.uk/emc/medicine/24136 | https://www.ncbi.nlm.nih.gov/pubmed/7861419

Nitrazepam (trade names: Alodorm, Apodorm, Arem, Mogadon, Nitrados, Nitrazadon, Nitrosun, Ormodon, Paxadorm, Remnos, and Somnite) is a hypnotic drug of the benzodiazepine class, indicated for the short-term relief of severe, disabling anxiety and insomnia. Nitrazepam has sedative and motor-impairing properties, as well as amnestic, anticonvulsant, and skeletal muscle relaxant effects. Nitrazepam is used to treat short-term sleeping problems (insomnia), namely difficulty falling asleep, frequent awakening, early awakening, or a combination of each. Nitrazepam is sometimes tried to treat epilepsy when other medications fail. It has been found to be more effective than clonazepam in the treatment of West syndrome, which is age-dependent epilepsy, affecting the very young. In uncontrolled studies, nitrazepam has shown effectiveness in infantile spasms and is sometimes considered when other anti-seizure drugs have failed. However, drowsiness, hypotonia, and most significantly tolerance to anti-seizure effects typically develop with long-term treatment, generally limiting Nitrazepam to acute seizure management. More common side effects may include: Central nervous system depression, including somnolence, dizziness, depressed mood, rage, violence, fatigue, ataxia, headache, vertigo, impairment of memory, impairment of motor functions, hangover feeling in the morning, slurred speech, decreased physical performance, numbed emotions, reduced alertness, muscle weakness, double vision, and inattention have been reported. Unpleasant dreams and rebound insomnia have also been reported. Nitrazepam is a long-acting benzodiazepine with an elimination half-life of 15–38 hours (mean elimination half-life 26 hours).

Originator

Sources: Journal of the American Chemical Society, Volume 82, Pages 5636-9, Journal,1960

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
38.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Insomin

Approved Use

Unknown
Primary
Alodorm

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Electrospray ionization gas-phase electrophoresis under ambient conditions and it's potential or high-speed separations.
2001 Feb
Heterogeneity of O6-alkylguanine DNA-alkyltransferase expression in human breast tumours.
2002 Jun 5
A population-based case-control teratologic study of nitrazepam, medazepam, tofisopam, alprazolum and clonazepam treatment during pregnancy.
2002 Mar 10
Citalopram in fatal poisoning cases.
2002 Mar 28
Medical treatment of patients with infantile spasms.
2002 Mar-Apr
Re: Gerson and triadafilopoulos--colorectal screening before herniorrhaphy.
2002 May
Direct injection micellar liquid chromatographic determination of benzodiazepines in serum.
2002 Nov 25
Sedative effects of the methanolic leaf extract of Newbouldia laevis in mice and rats.
2002 Nov-Dec
Segmental ion spray LC-MS-MS analysis of benzodiazepines in hair of psychiatric patients.
2002 Oct
[Determination of benzodiazepine derivatives mixture by high performance liquid chromatography].
2003
[Diagnostics and treatment of sleep disorders in elderly people].
2003 Apr-Jun
Short-term nonhormonal and nonsteroid treatment in West syndrome.
2003 Aug
Treatment of infantile spasms: the ideal and the mundane.
2003 Aug
Alpha-adrenergic blockade: a possible mechanism of tocolytic action of certain benzodiazepines in a postpartum rat model in vivo.
2003 Jan 24
Benzodiazepines block alpha2-containing inhibitory glycine receptors in embryonic mouse hippocampal neurons.
2003 Jul
Tail-swing behavior: a novel animal model for anxiety.
2003 Jun
[A case of intractable epilepsy showing frequent gelastic seizures by administration of clobazam].
2003 Sep
[Clonazepam as a therapeutic adjunct to improve the management of depression].
2004 Apr
Toxicity of nitrazepam in the elderly: a report from the Boston Collaborative Drug Surveillance Program. 1978.
2004 Dec
The detection of drugs of abuse in fingerprints using Raman spectroscopy I: latent fingerprints.
2004 Feb
Risk and benefit of drug use during pregnancy.
2005
Determination of 14 benzodiazepines and hydroxy metabolites, zaleplon and zolpidem as tert-butyldimethylsilyl derivatives compared with other common silylating reagents in whole blood by gas chromatography-mass spectrometry.
2005 Apr 25
An analysis of epilepsy with chromosomal abnormalities.
2005 Aug
Rapid in vivo Taxotere quantitative chemosensitivity response by 4.23 Tesla sodium MRI and histo-immunostaining features in N-Methyl-N-Nitrosourea induced breast tumors in rats.
2005 Aug 3
Sialorrhea: a review of a vexing, often unrecognized sign of oropharyngeal and esophageal disease.
2005 Feb
Effect of antiepileptic drug polytherapy on crystalluria.
2005 Feb
QT interval prolongation after sertraline overdose: a case report.
2005 Jul 19
[Pharmacological profiles of benzodiazepinergic hypnotics and correlations with receptor subtypes].
2005 Jun
Patient perspectives: Tijuana cancer clinics in the post-NAFTA era.
2005 Mar
The interaction of lipophilic drugs with intestinal fatty acid-binding protein.
2005 May 6
Primary care use of antipsychotic drugs: an audit and intervention study.
2005 Nov 29
Antimicrobial proteins and polypeptides in pulmonary innate defence.
2006 Feb 17
Anti-conflict effects of benzodiazepines in rhesus monkeys: relationship with therapeutic doses in humans and role of GABAA receptors.
2006 Jan
Voltammetric behavior of nitrazepam and its determination in serum using liquid chromatography with redox mode dual-electrode detection.
2006 Jan 15
Streambed microstructure predicts evolution of development and life history mode in the plethodontid salamander Eurycea tynerensis.
2006 Mar 2
Quantification of benzodiazepines in whole blood and serum.
2006 Nov
Neonatal anemia and hydrops fetalis after maternal mycophenolate mofetil use.
2007 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Oral, 5 or 10 mg at bedtime
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 16 15:58:00 UTC 2022
Edited
by admin
on Fri Dec 16 15:58:00 UTC 2022
Record UNII
9CLV70W7HS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NITRAZEPAM
EP   INN   MART.   MI   USAN   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
NITRAZEPAM [MI]
Common Name English
RO-5-3059
Code English
NITRAZEPAM [USAN]
Common Name English
1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one
Systematic Name English
RO-53059
Code English
2H-1,4-BENZODIAZEPIN-2-ONE, 1,3-DIHYDRO-7-NITRO-5-PHENYL-
Systematic Name English
NITRAZEPAM [JAN]
Common Name English
NSC-58775
Code English
NITRAZEPAMUM [WHO-IP LATIN]
Common Name English
RO 5-3059
Code English
NITRAZEPAM [MART.]
Common Name English
RO 4-5360
Code English
Nitrazepam [WHO-DD]
Common Name English
NITRAZEPAM [WHO-IP]
Common Name English
NITRAZEPAM [EP MONOGRAPH]
Common Name English
nitrazepam [INN]
Common Name English
N05CD02
Code English
RO-45360
Code English
BENZALIN
Brand Name English
RO-4-5360
Code English
Classification Tree Code System Code
WHO-VATC QN05CD02
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
NCI_THESAURUS C1012
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
WHO-ATC N05CD02
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
DEA NO. 2834
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
Code System Code Type Description
DRUG BANK
DB01595
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
DRUG CENTRAL
1945
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
INN
2121
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
NSC
58775
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
MERCK INDEX
M7931
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY Merck Index
PUBCHEM
4506
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
NCI_THESAURUS
C87674
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
LACTMED
Nitrazepam
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
ChEMBL
CHEMBL13209
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
EPA CompTox
DTXSID5023372
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
MESH
D009567
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
CAS
146-22-5
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
WIKIPEDIA
NITRAZEPAM
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
FDA UNII
9CLV70W7HS
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NITRAZEPAM
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY Description: A yellow, crystalline powder; odourless or almost odourless. Solubility: Practically insoluble in water; slightly soluble in ethanol (~750 g/l) TS; very slightly soluble in ether R. Category: Sedative; hypnotic. Storage: Nitrazepam should be kept in a well-closed container, protected from light. Definition: Nitrazepam contains not less than 98.5% and not more than 101.0% of C15H11N3O3, calculated with reference to thedried substance.
CHEBI
7581
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
EVMPD
SUB09318MIG
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
RXCUI
7440
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY RxNorm
ECHA (EC/EINECS)
205-665-2
Created by admin on Fri Dec 16 15:58:00 UTC 2022 , Edited by admin on Fri Dec 16 15:58:00 UTC 2022
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
IN-VIVO
URINE
Related Record Type Details
ACTIVE MOIETY