Identification
- Summary
Nitrazepam is a long-acting benzodiazepine with intermediate onset commonly used to treat panic disorders, severe anxiety, insomnia, and seizures.
- Brand Names
- Mogadon
- Generic Name
- Nitrazepam
- DrugBank Accession Number
- DB01595
- Background
A benzodiazepine derivative used as an anticonvulsant and hypnotic.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Nitrazepam (DB01595)
- Weight
- Average: 281.2661
Monoisotopic: 281.080041233 - Chemical Formula
- C15H11N3O3
- Synonyms
- 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one
- 2,3-dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-one
- 7-nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one
- 7-nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
- N-desmethylnimetazepam
- Nitrazepam
- Nitrazépam
- Nitrazepamum
- External IDs
- N05CD02
- NSC-58775
- RO 4-5360
- RO 5-3059
Pharmacology
- Indication
Used to treat short-term sleeping problems (insomnia), such as difficulty falling asleep, frequent awakenings during the night, and early-morning awakening.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Insomnia •••••••••••• Management of Myoclonic seizures •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Nitrazepam is a type of benzodiazepine drug. It is a powerful hypnotic drug which possesses strong sedative, anxiolytic, amnestic, anticonvulsant, and skeletal muscle relaxant properties. Nitrazepam shortens the time required to fall asleep and lengthens the duration of sleep. It is also useful for the management of myoclonic seizures.
- Mechanism of action
Nitrazepam belongs to a group of medicines called benzodiazepines. This drug affects central benzodiazepine receptors, which are associated with inhibitory GABA (gamma amino butyric acid)receptors, leading to enhanced GABA binding activity. GABA is a major neurotransmitter in the brain, which causes somnolence, relaxation of muscles, a decrease in anxiety and general central nervous system depression. Nitrazepam has anticonvulsant properties that may be attributed to its ability to bind to voltage-dependent sodium channels. Sustained repetitive firing seems to be limited by benzodiazepines effect of slowing recovery of sodium channels from inactivation.
Target Actions Organism AGABA(A) Receptor positive allosteric modulatorHumans AGABA(A) Receptor Benzodiazepine Binding Site ligandHumans USodium channel protein type 1 subunit alpha other/unknownHumans - Absorption
Bioavailability is 53-94% following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
15-38 hours (mean elimination half life 26 hours).
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
An overdose of nitrazepam may lead to impaired breathing, dizziness, decreased cognition and balance, bluish nails and lips, slurred speech, and extreme somnolence, among others. In severe overdose, these symptoms may progress to a coma with a possibility of death.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Nitrazepam is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Nitrazepam can be increased when it is combined with Abametapir. Acetaminophen Nitrazepam may increase the hepatotoxic activities of Acetaminophen. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Nitrazepam. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Nitrazepam. - Food Interactions
- Avoid alcohol.
- Limit caffeine intake.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Alodorm / Apodorm / Arem / Atempol / Benzalin / Calsmin / Eatan / Eunoctin / Gerson / Hipnax / Hipsal / Ibrovek / Imeson / Imesont / Insoma / Nelbon / Nelmat / Neozepam / Neuchlonic / Nitrados / Nitrosun / Ormodon / Pacisyn / Paxadorm / Paxisyn / Pelson / Persopit / Radedorm / Relact / Remnos / Somitran / Somnite / Sonebon / Sonnolin / Surem / Trazenin / Unisomnia
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mogadon Tablet 5 mg Oral Aa Pharma Inc 1980-12-31 Not applicable Canada 
Mogadon Tablet 10 mg Oral Aa Pharma Inc 1980-12-31 Not applicable Canada Nitrazadon Tablet 10 mg Oral Aa Pharma Inc 1996-11-08 2014-06-25 Canada Nitrazadon Tablet 5 mg Oral Aa Pharma Inc 1996-11-08 2014-06-25 Canada Nitrazepam-10 Tablet 10 mg Oral Pro Doc Limitee 2004-07-29 2010-07-13 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-nitrazepam Tablet 10 mg Oral Apotex Corporation 2002-09-17 Not applicable Canada Apo-nitrazepam Tablet 5 mg Oral Apotex Corporation 2002-09-17 Not applicable Canada Sandoz Nitrazepam Tablet 10 mg Oral Sandoz Canada Incorporated 1997-12-02 2018-08-01 Canada Sandoz Nitrazepam Tablet 5 mg Oral Sandoz Canada Incorporated 1997-12-02 2018-08-01 Canada
Categories
- ATC Codes
- N05CD02 — Nitrazepam
- Drug Categories
- Anti-Anxiety Agents
- Anticonvulsants
- Benzazepines
- Benzodiazepine hypnotics and sedatives
- Benzodiazepines and benzodiazepine derivatives
- Benzodiazepinones
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- GABA Agents
- GABA Modulators
- Heterocyclic Compounds, Fused-Ring
- Hypnotics and Sedatives
- Muscle Relaxants
- Muscle Relaxants, Centrally Acting Agents
- Nervous System
- Neurotransmitter Agents
- Psycholeptics
- Psychotropic Drugs
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzodiazepines
- Sub Class
- 1,4-benzodiazepines
- Direct Parent
- 1,4-benzodiazepines
- Alternative Parents
- Alpha amino acids and derivatives / Nitroaromatic compounds / Benzene and substituted derivatives / Secondary carboxylic acid amides / Lactams / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Azacyclic compounds / Organopnictogen compounds show 4 more
- Substituents
- 1,4-benzodiazepine / Allyl-type 1,3-dipolar organic compound / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / C-nitro compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative show 18 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- C-nitro compound, 1,4-benzodiazepinone (CHEBI:7581)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 9CLV70W7HS
- CAS number
- 146-22-5
- InChI Key
- KJONHKAYOJNZEC-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 7-nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
- SMILES
- [O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2)C=C1
References
- General References
- Rickels K: The clinical use of hypnotics: indications for use and the need for a variety of hypnotics. Acta Psychiatr Scand Suppl. 1986;332:132-41. [Article]
- Robertson MD, Drummer OH: Postmortem drug metabolism by bacteria. J Forensic Sci. 1995 May;40(3):382-6. [Article]
- Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Article]
- Podhorna J, Krsiak M: Behavioural effects of a benzodiazepine receptor partial agonist, Ro 19-8022, in the social conflict test in mice. Behav Pharmacol. 2000 Apr;11(2):143-51. [Article]
- Nowakowska E, Chodera A: Studies on the involvement of opioid mechanism in the locomotor effects of benzodiazepines in rats. Pharmacol Biochem Behav. 1991 Feb;38(2):265-6. [Article]
- External Links
- Human Metabolome Database
- HMDB0015534
- KEGG Drug
- D00531
- KEGG Compound
- C07487
- PubChem Compound
- 4506
- PubChem Substance
- 46505806
- ChemSpider
- 4350
- BindingDB
- 50020856
- 7440
- ChEBI
- 7581
- ChEMBL
- CHEMBL13209
- ZINC
- ZINC000004311748
- Therapeutic Targets Database
- DAP000691
- PharmGKB
- PA10242
- Wikipedia
- Nitrazepam
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Unknown Status Treatment Epilepsy 1 3 Completed Treatment Sleep Initiation and Maintenance Disorders 1 3 Terminated Treatment Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia 1 2 Completed Treatment Epilepsy / Infantile Spasms (IS) 1 2 Not Yet Recruiting Treatment Pyelonephritis / Urinary Tract Infection 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral Tablet Oral 10 mg/1 Tablet Oral Tablet Oral 5 mg Tablet Oral 10 mg - Prices
Unit description Cost Unit Mogadon 10 mg Tablet 0.24USD tablet Mogadon 5 mg Tablet 0.16USD tablet Apo-Nitrazepam 10 mg Tablet 0.13USD tablet Nitrazadon 10 mg Tablet 0.11USD tablet Sandoz Nitrazepam 10 mg Tablet 0.11USD tablet Apo-Nitrazepam 5 mg Tablet 0.09USD tablet Nitrazadon 5 mg Tablet 0.08USD tablet Sandoz Nitrazepam 5 mg Tablet 0.08USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 225 °C PhysProp logP 2.25 HANSCH,C ET AL. (1995) logS -3.8 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.0299 mg/mL ALOGPS logP 1.95 ALOGPS logP 2.55 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 11.66 Chemaxon pKa (Strongest Basic) 2.65 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 84.6 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 78.21 m3·mol-1 Chemaxon Polarizability 27.67 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9925 Blood Brain Barrier + 0.9802 Caco-2 permeable + 0.5176 P-glycoprotein substrate Substrate 0.5785 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.9205 Renal organic cation transporter Non-inhibitor 0.8307 CYP450 2C9 substrate Non-substrate 0.7695 CYP450 2D6 substrate Non-substrate 0.8583 CYP450 3A4 substrate Substrate 0.6725 CYP450 1A2 substrate Inhibitor 0.7569 CYP450 2C9 inhibitor Non-inhibitor 0.6133 CYP450 2D6 inhibitor Non-inhibitor 0.8986 CYP450 2C19 inhibitor Inhibitor 0.5682 CYP450 3A4 inhibitor Inhibitor 0.6791 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5645 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.7197 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5397 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9904 hERG inhibition (predictor II) Non-inhibitor 0.8498
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 176.0240718 predictedDarkChem Lite v0.1.0 [M-H]- 176.1321718 predictedDarkChem Lite v0.1.0 [M-H]- 158.75526 predictedDeepCCS 1.0 (2019) [M+H]+ 176.5661718 predictedDarkChem Lite v0.1.0 [M+H]+ 176.3501718 predictedDarkChem Lite v0.1.0 [M+H]+ 161.11327 predictedDeepCCS 1.0 (2019) [M+Na]+ 176.1739718 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.8204718 predictedDarkChem Lite v0.1.0 [M+Na]+ 167.81229 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- Curator comments
- The GABA(A) receptor is pentameric (i.e. comprising 5 subunit proteins) and therefore has a multitude of potential isoforms. The above target is a collection of all possible GABA(A) subunits that may participate in the formation of the pentameric receptor and is not meant to imply direct a drug-protein interaction for each individual subunit.
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
- Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- Curator comments
- Benzodiazepines modulate GABA(A) function by binding at the interface between alpha (α) and gamma (γ) subunits. Of the 6 α-subunits, only 4 (α-1, -2, -3, and -5) participate in the formation of this binding site. The above target is a collection of all α- and γ-subunits that are known to participate in the formation of the benzodiazepine binding site.
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
- Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other/unknown
- General Function
- Voltage-gated sodium channel activity
- Specific Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...
- Gene Name
- SCN1A
- Uniprot ID
- P35498
- Uniprot Name
- Sodium channel protein type 1 subunit alpha
- Molecular Weight
- 228969.49 Da
References
- McLean MJ, Macdonald RL: Benzodiazepines, but not beta carbolines, limit high frequency repetitive firing of action potentials of spinal cord neurons in cell culture. J Pharmacol Exp Ther. 1988 Feb;244(2):789-95. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Vrzal R, Kubesova K, Pavek P, Dvorak Z: Benzodiazepines medazepam and midazolam are activators of pregnane X receptor and weak inducers of CYP3A4: investigation in primary cultures of human hepatocytes and hepatocarcinoma cell lines. Toxicol Lett. 2010 Mar 15;193(2):183-8. doi: 10.1016/j.toxlet.2010.01.004. Epub 2010 Jan 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Tassaneeyakul W, Birkett DJ, Miners JO: Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica. 1998 Mar;28(3):293-301. doi: 10.1080/004982598239579 . [Article]
Drug created at August 29, 2007 17:49 / Updated at February 20, 2024 23:55