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
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)
DescriptionSources: https://www.drugbank.ca/drugs/DB01595Curator'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
Sources: https://www.drugbank.ca/drugs/DB01595
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).
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7861419 |
38.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Insomin Approved UseUnknown |
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Sources: http://www.rlsnet.ru/tn_index_id_6300.htm |
Primary | Alodorm Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Studies on the involvement of opioid mechanism in the locomotor effects of benzodiazepines in rats. | 1991 Feb |
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[West syndrome--new therapeutic approach]. | 2001 May-Jun |
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[Experimental pharmacodynamic study on the anti-convulsion effect of shenpu decoction]. | 2001 Nov |
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[Ultraviolet spectrophotometric determination of psychotropic drug mixtures]. | 2002 |
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[Analysis of benzodiazepine derivative mixture by gas-liquid chromatography]. | 2002 |
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[Poisonings with psychotropic drug mixtures: analysis using the thin-layer chromatography method]. | 2002 |
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Sedative effects of the methanolic leaf extract of Newbouldia laevis in mice and rats. | 2002 Nov-Dec |
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Segmental ion spray LC-MS-MS analysis of benzodiazepines in hair of psychiatric patients. | 2002 Oct |
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[Analysis of 7-aminonitrazepam in urine by trimethylsilyl derivatization-gas chromatography/mass spectrometry]. | 2002 Sep |
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The role of benzodiazepines in elderly suicides. | 2003 |
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Quantitative determination of diazepam, nitrazepam and flunitrazepam in tablets using thin-layer chromatography-densitometry technique. | 2003 Apr 10 |
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[Diagnostics and treatment of sleep disorders in elderly people]. | 2003 Apr-Jun |
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Short-term nonhormonal and nonsteroid treatment in West syndrome. | 2003 Aug |
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Treatment of infantile spasms: the ideal and the mundane. | 2003 Aug |
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Alpha-adrenergic blockade: a possible mechanism of tocolytic action of certain benzodiazepines in a postpartum rat model in vivo. | 2003 Jan 24 |
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Tissue distribution of nitrazepam and 7-aminonitrazepam in a case of nitrazepam intoxication. | 2003 Jan 28 |
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Tail-swing behavior: a novel animal model for anxiety. | 2003 Jun |
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Residual effects of hypnotics: epidemiology and clinical implications. | 2004 |
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[Clonazepam as a therapeutic adjunct to improve the management of depression]. | 2004 Apr |
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[Benzodiazepine (clonazepam, nitrazepam, diazepam)]. | 2004 Dec |
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Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis. | 2004 Jul |
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The detection of drugs of abuse in fingerprints using Raman spectroscopy II: cyanoacrylate-fumed fingerprints. | 2004 Jul |
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Modeling the deagglomeration of micronized benzodiazepines from powder mixtures added to dissolution media. | 2004 Jun |
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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 |
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Practice parameter: medical treatment of infantile spasms: report of the American Academy of Neurology and the Child Neurology Society. | 2004 May 25 |
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Clinical review: how to identify high-risk surgical patients. | 2004 Oct |
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Risk and benefit of drug use during pregnancy. | 2005 |
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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 |
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Effect of antiepileptic drug polytherapy on crystalluria. | 2005 Feb |
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Epilepsy in Wolf-Hirschhorn syndrome (4p-). | 2005 Jan |
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Solid-phase extraction of methadone enantiomers and benzodiazepines in biological fluids by two polymeric cartridges for liquid chromatographic analysis. | 2005 Jan 25 |
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[Pharmacological profiles of benzodiazepinergic hypnotics and correlations with receptor subtypes]. | 2005 Jun |
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Patient perspectives: Tijuana cancer clinics in the post-NAFTA era. | 2005 Mar |
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The interaction of lipophilic drugs with intestinal fatty acid-binding protein. | 2005 May 6 |
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Models of treatment with antipsychotics of the schizophrenic patients. | 2005 Nov |
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Hypnosis for treatment of insomnia in school-age children: a retrospective chart review. | 2006 Aug 16 |
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Primary invasive aspergillosis of the digestive tract: report of two cases and review of the literature. | 2006 Dec |
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Antimicrobial proteins and polypeptides in pulmonary innate defence. | 2006 Feb 17 |
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[Changes in the sale and use of flunitrazepam in Norway after 1999]. | 2006 Feb 23 |
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Voltammetric behavior of nitrazepam and its determination in serum using liquid chromatography with redox mode dual-electrode detection. | 2006 Jan 15 |
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Cross-sensitivity in a child with anticonvulsant hypersensitivity syndrome. | 2006 Jul-Aug |
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Intrastrain variations in anxiolytic effect of nitrazepam in mice. | 2006 Jul-Sep |
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Solubility of selected derivatives of 1,4-benzodiazepin-2-one in solid dispersions in PEG 6000. | 2006 Mar-Apr |
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Quantification of benzodiazepines in whole blood and serum. | 2006 Nov |
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Different effects of light food on pharmacokinetics and pharmacodynamics of three benzodiazepines, quazepam, nitrazepam and diazepam. | 2007 Feb |
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Drug screening of preserved oral fluid by liquid chromatography-tandem mass spectrometry. | 2007 Feb |
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Surviving against all odds: analysis of 6 case studies of patients with cancer who followed the Gerson therapy. | 2007 Mar |
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The effect of placebo administration on the first-night effect in healthy young volunteers. | 2007 May 9 |
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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 |
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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
Sources: https://www.drugs.com/mmx/nitrazepam.html
Oral, 5 or 10 mg at bedtime
Route of Administration:
Oral
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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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DB01595
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1945
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100000091767
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2121
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58775
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m7931
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4506
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C87674
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Nitrazepam
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CHEMBL13209
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DTXSID5023372
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D009567
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146-22-5
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NITRAZEPAM
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9CLV70W7HS
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NITRAZEPAM
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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. | ||
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7581
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SUB09318MIG
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7440
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205-665-2
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)