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)
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 |
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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Electrospray ionization gas-phase electrophoresis under ambient conditions and it's potential or high-speed separations. | 2001 Feb |
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Heterogeneity of O6-alkylguanine DNA-alkyltransferase expression in human breast tumours. | 2002 Jun 5 |
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A population-based case-control teratologic study of nitrazepam, medazepam, tofisopam, alprazolum and clonazepam treatment during pregnancy. | 2002 Mar 10 |
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Citalopram in fatal poisoning cases. | 2002 Mar 28 |
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Medical treatment of patients with infantile spasms. | 2002 Mar-Apr |
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Re: Gerson and triadafilopoulos--colorectal screening before herniorrhaphy. | 2002 May |
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Direct injection micellar liquid chromatographic determination of benzodiazepines in serum. | 2002 Nov 25 |
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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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[Determination of benzodiazepine derivatives mixture by high performance liquid chromatography]. | 2003 |
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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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Benzodiazepines block alpha2-containing inhibitory glycine receptors in embryonic mouse hippocampal neurons. | 2003 Jul |
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Tail-swing behavior: a novel animal model for anxiety. | 2003 Jun |
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[A case of intractable epilepsy showing frequent gelastic seizures by administration of clobazam]. | 2003 Sep |
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[Clonazepam as a therapeutic adjunct to improve the management of depression]. | 2004 Apr |
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Toxicity of nitrazepam in the elderly: a report from the Boston Collaborative Drug Surveillance Program. 1978. | 2004 Dec |
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The detection of drugs of abuse in fingerprints using Raman spectroscopy I: latent fingerprints. | 2004 Feb |
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Risk and benefit of drug use during pregnancy. | 2005 |
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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 |
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An analysis of epilepsy with chromosomal abnormalities. | 2005 Aug |
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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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Sialorrhea: a review of a vexing, often unrecognized sign of oropharyngeal and esophageal disease. | 2005 Feb |
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Effect of antiepileptic drug polytherapy on crystalluria. | 2005 Feb |
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QT interval prolongation after sertraline overdose: a case report. | 2005 Jul 19 |
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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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Primary care use of antipsychotic drugs: an audit and intervention study. | 2005 Nov 29 |
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Antimicrobial proteins and polypeptides in pulmonary innate defence. | 2006 Feb 17 |
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Anti-conflict effects of benzodiazepines in rhesus monkeys: relationship with therapeutic doses in humans and role of GABAA receptors. | 2006 Jan |
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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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Streambed microstructure predicts evolution of development and life history mode in the plethodontid salamander Eurycea tynerensis. | 2006 Mar 2 |
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Quantification of benzodiazepines in whole blood and serum. | 2006 Nov |
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Neonatal anemia and hydrops fetalis after maternal mycophenolate mofetil use. | 2007 Jan |
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
Substance Class |
Chemical
Created
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Record UNII |
9CLV70W7HS
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Record Status |
Validated (UNII)
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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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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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URINE
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IN-VIVO
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ACTIVE MOIETY |