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

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
Studies on the involvement of opioid mechanism in the locomotor effects of benzodiazepines in rats.
1991 Feb
[West syndrome--new therapeutic approach].
2001 May-Jun
[Experimental pharmacodynamic study on the anti-convulsion effect of shenpu decoction].
2001 Nov
[Ultraviolet spectrophotometric determination of psychotropic drug mixtures].
2002
[Analysis of benzodiazepine derivative mixture by gas-liquid chromatography].
2002
[Poisonings with psychotropic drug mixtures: analysis using the thin-layer chromatography method].
2002
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
[Analysis of 7-aminonitrazepam in urine by trimethylsilyl derivatization-gas chromatography/mass spectrometry].
2002 Sep
The role of benzodiazepines in elderly suicides.
2003
Quantitative determination of diazepam, nitrazepam and flunitrazepam in tablets using thin-layer chromatography-densitometry technique.
2003 Apr 10
[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
Tissue distribution of nitrazepam and 7-aminonitrazepam in a case of nitrazepam intoxication.
2003 Jan 28
Tail-swing behavior: a novel animal model for anxiety.
2003 Jun
Residual effects of hypnotics: epidemiology and clinical implications.
2004
[Clonazepam as a therapeutic adjunct to improve the management of depression].
2004 Apr
[Benzodiazepine (clonazepam, nitrazepam, diazepam)].
2004 Dec
Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis.
2004 Jul
The detection of drugs of abuse in fingerprints using Raman spectroscopy II: cyanoacrylate-fumed fingerprints.
2004 Jul
Modeling the deagglomeration of micronized benzodiazepines from powder mixtures added to dissolution media.
2004 Jun
Optimisation of high-performance liquid chromatography with diode array detection using an automatic peak tracking procedure based on augmented iterative target transformation factor analysis.
2004 Mar
Practice parameter: medical treatment of infantile spasms: report of the American Academy of Neurology and the Child Neurology Society.
2004 May 25
Clinical review: how to identify high-risk surgical patients.
2004 Oct
Risk and benefit of drug use during pregnancy.
2005
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
Effect of antiepileptic drug polytherapy on crystalluria.
2005 Feb
Epilepsy in Wolf-Hirschhorn syndrome (4p-).
2005 Jan
Solid-phase extraction of methadone enantiomers and benzodiazepines in biological fluids by two polymeric cartridges for liquid chromatographic analysis.
2005 Jan 25
[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
Models of treatment with antipsychotics of the schizophrenic patients.
2005 Nov
Hypnosis for treatment of insomnia in school-age children: a retrospective chart review.
2006 Aug 16
Primary invasive aspergillosis of the digestive tract: report of two cases and review of the literature.
2006 Dec
Antimicrobial proteins and polypeptides in pulmonary innate defence.
2006 Feb 17
[Changes in the sale and use of flunitrazepam in Norway after 1999].
2006 Feb 23
Voltammetric behavior of nitrazepam and its determination in serum using liquid chromatography with redox mode dual-electrode detection.
2006 Jan 15
Cross-sensitivity in a child with anticonvulsant hypersensitivity syndrome.
2006 Jul-Aug
Intrastrain variations in anxiolytic effect of nitrazepam in mice.
2006 Jul-Sep
Solubility of selected derivatives of 1,4-benzodiazepin-2-one in solid dispersions in PEG 6000.
2006 Mar-Apr
Quantification of benzodiazepines in whole blood and serum.
2006 Nov
Different effects of light food on pharmacokinetics and pharmacodynamics of three benzodiazepines, quazepam, nitrazepam and diazepam.
2007 Feb
Drug screening of preserved oral fluid by liquid chromatography-tandem mass spectrometry.
2007 Feb
Surviving against all odds: analysis of 6 case studies of patients with cancer who followed the Gerson therapy.
2007 Mar
The effect of placebo administration on the first-night effect in healthy young volunteers.
2007 May 9
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 Jan 15
Long-term stability of various drugs and metabolites in urine, and preventive measures against their decomposition with special attention to filtration sterilization.
2008 Jan 30
Patents

Sample Use Guides

In Vivo Use Guide
Oral, 5 or 10 mg at bedtime
Route of Administration: Oral
In Vitro Use Guide
Unknown
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
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NCI_THESAURUS C1012
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WHO-ATC N05CD02
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DEA NO. 2834
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Code System Code Type Description
DRUG BANK
DB01595
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PRIMARY
DRUG CENTRAL
1945
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PRIMARY
SMS_ID
100000091767
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PRIMARY
INN
2121
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PRIMARY
NSC
58775
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PRIMARY
MERCK INDEX
m7931
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PRIMARY Merck Index
PUBCHEM
4506
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PRIMARY
NCI_THESAURUS
C87674
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PRIMARY
LACTMED
Nitrazepam
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PRIMARY
ChEMBL
CHEMBL13209
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PRIMARY
EPA CompTox
DTXSID5023372
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PRIMARY
MESH
D009567
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PRIMARY
CAS
146-22-5
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PRIMARY
WIKIPEDIA
NITRAZEPAM
Created by admin on Fri Dec 15 15:01:57 GMT 2023 , Edited by admin on Fri Dec 15 15:01:57 GMT 2023
PRIMARY
FDA UNII
9CLV70W7HS
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NITRAZEPAM
Created by admin on Fri Dec 15 15:01:57 GMT 2023 , Edited by admin on Fri Dec 15 15:01:57 GMT 2023
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 15 15:01:57 GMT 2023 , Edited by admin on Fri Dec 15 15:01:57 GMT 2023
PRIMARY
EVMPD
SUB09318MIG
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PRIMARY
RXCUI
7440
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PRIMARY RxNorm
ECHA (EC/EINECS)
205-665-2
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PRIMARY