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=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=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
Anemia in children with chronic kidney disease.
2008-02
Long-term stability of various drugs and metabolites in urine, and preventive measures against their decomposition with special attention to filtration sterilization.
2008-01-30
Comparison of molecularly imprinted solid-phase extraction (MISPE) with classical solid-phase extraction (SPE) for the detection of benzodiazepines in post-mortem hair samples.
2008-01-15
Solubility of selected derivatives of 1,4-benzodiazepin-2-one in solid dispersions in PEG 6000.
2007-05-23
The effect of placebo administration on the first-night effect in healthy young volunteers.
2007-05-09
Extraction and analysis of clonazepam and 7-aminoclonazepam in whole blood using a dual internal standard methodology.
2007-03-02
Surviving against all odds: analysis of 6 case studies of patients with cancer who followed the Gerson therapy.
2007-03
Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats.
2007-02
Different effects of light food on pharmacokinetics and pharmacodynamics of three benzodiazepines, quazepam, nitrazepam and diazepam.
2007-02
Drug screening of preserved oral fluid by liquid chromatography-tandem mass spectrometry.
2007-02
Separation of 1,4-benzodiazepines by micellar elektrokinetic capillary chromatography.
2007-01-10
Neonatal anemia and hydrops fetalis after maternal mycophenolate mofetil use.
2007-01
Intrastrain variations in anxiolytic effect of nitrazepam in mice.
2006-12-30
Primary invasive aspergillosis of the digestive tract: report of two cases and review of the literature.
2006-12
Prospective study of first-choice topiramate therapy in newly diagnosed infantile spasms.
2006-11-11
Quantification of benzodiazepines in whole blood and serum.
2006-11
A survey of buprenorphine related deaths in Singapore.
2006-10-16
Detection of benzodiazepines in hair using ELISA and LC-ESI-MS-MS.
2006-09
Hypnosis for treatment of insomnia in school-age children: a retrospective chart review.
2006-08-16
Cross-sensitivity in a child with anticonvulsant hypersensitivity syndrome.
2006-08-11
Quality of life in patients with various Barrett's esophagus associated health states.
2006-08-02
Modeling cumulative dose and exposure duration provided insights regarding the associations between benzodiazepines and injuries.
2006-04
Extraction and analysis of flunitrazepam/7-aminoflunitrazepam in blood and urine by LC-PDA and GC-MS using butyl SPE columns.
2006-03-10
Streambed microstructure predicts evolution of development and life history mode in the plethodontid salamander Eurycea tynerensis.
2006-03-02
[Changes in the sale and use of flunitrazepam in Norway after 1999].
2006-02-23
Antimicrobial proteins and polypeptides in pulmonary innate defence.
2006-02-17
Voltammetric behavior of nitrazepam and its determination in serum using liquid chromatography with redox mode dual-electrode detection.
2006-01-15
Anti-conflict effects of benzodiazepines in rhesus monkeys: relationship with therapeutic doses in humans and role of GABAA receptors.
2006-01
Primary care use of antipsychotic drugs: an audit and intervention study.
2005-11-29
Models of treatment with antipsychotics of the schizophrenic patients.
2005-11
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.
2005-08-03
An analysis of epilepsy with chromosomal abnormalities.
2005-08
QT interval prolongation after sertraline overdose: a case report.
2005-07-19
[Pharmacological profiles of benzodiazepinergic hypnotics and correlations with receptor subtypes].
2005-06
The interaction of lipophilic drugs with intestinal fatty acid-binding protein.
2005-05-06
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.
2005-04-25
Patient perspectives: Tijuana cancer clinics in the post-NAFTA era.
2005-03
Sialorrhea: a review of a vexing, often unrecognized sign of oropharyngeal and esophageal disease.
2005-02
Effect of antiepileptic drug polytherapy on crystalluria.
2005-02
Solid-phase extraction of methadone enantiomers and benzodiazepines in biological fluids by two polymeric cartridges for liquid chromatographic analysis.
2005-01-25
[West syndrome--new therapeutic approach].
2005-01-11
Epilepsy in Wolf-Hirschhorn syndrome (4p-).
2005-01
Risk and benefit of drug use during pregnancy.
2005
[Benzodiazepine (clonazepam, nitrazepam, diazepam)].
2004-12
Toxicity of nitrazepam in the elderly: a report from the Boston Collaborative Drug Surveillance Program. 1978.
2004-12
Nutrition and cancer: a review of the evidence for an anti-cancer diet.
2004-10-20
Clinical review: how to identify high-risk surgical patients.
2004-10
[Analysis of 7-aminonitrazepam in urine by trimethylsilyl derivatization-gas chromatography/mass spectrometry].
2002-09
Depersonalization following nitrazepam withdrawal.
1992-01-15
Studies on the involvement of opioid mechanism in the locomotor effects of benzodiazepines in rats.
1991-02
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 Mon Mar 31 17:35:59 GMT 2025
Edited
by admin
on Mon Mar 31 17:35:59 GMT 2025
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
BENZALIN
Preferred 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
RO-4-5360
Code English
Classification Tree Code System Code
WHO-VATC QN05CD02
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
NCI_THESAURUS C1012
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
WHO-ATC N05CD02
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
DEA NO. 2834
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
Code System Code Type Description
DRUG BANK
DB01595
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
DRUG CENTRAL
1945
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
SMS_ID
100000091767
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PRIMARY
INN
2121
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
NSC
58775
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
MERCK INDEX
m7931
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY Merck Index
PUBCHEM
4506
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
NCI_THESAURUS
C87674
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
LACTMED
Nitrazepam
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
ChEMBL
CHEMBL13209
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
EPA CompTox
DTXSID5023372
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
MESH
D009567
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
CAS
146-22-5
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
WIKIPEDIA
NITRAZEPAM
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
FDA UNII
9CLV70W7HS
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NITRAZEPAM
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
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 Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
EVMPD
SUB09318MIG
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
RXCUI
7440
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
205-665-2
Created by admin on Mon Mar 31 17:35:59 GMT 2025 , Edited by admin on Mon Mar 31 17:35:59 GMT 2025
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
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ACTIVE MOIETY