7-nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

• ChemBase ID: 1373
• Molecular Formular: C15H11N3O3
• Molecular Mass: 281.26614
• Monoisotopic Mass: 281.08004123
• SMILES: O=C1Nc2c(C(=NC1)c1ccccc1)cc([N+](=O)[O-])cc2
• Canonical SMILES: O=C1CN=C(c2c(N1)ccc(c2)[N+](=O)[O-])c1ccccc1
• 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)
• InChIKey: KJONHKAYOJNZEC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC Traditional name: nitrazepam; novanox; 7-nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• Brand Name: Magadon; Megadon; Mitidin; Mogadan; Mogadon; Mogadone; Nelbon; Nelmat; Neozepam; Neuchlonic; Nitrados; Nitravet; Nitrazadon; Nitrazepam-10; Nitrazepam-5; Nitrempax; Nitrenpax; Noctesed; Pacisyn; Paxisyn; Pelson; Persopit; Radedorm; Relact; Remnos; Sandoz nitrazepam; Somitran; Somnased; Somnibel; Somnite; Sonebon; Sonebon tofraniln a; Sonnolin; Surem; Trazenin; Unisomnia; Alodorm; Atempol; Benzalin; Calsamin; Calsmin; Cerson; Dormicum; Dormin-5; Dormo-puren; Dumolid; Eatan; Eatan n; Epibenzalin; Epinelbon; Eunoctin; Eunoktin; Gerson; Hipnax; Hipsal; Ibrovek; Imeson; Imesont; Insomin; Ipersed; LA 1 (VAN); Apo-nitrazepam tablets BP; Apodorm; Alodorm, Arem, Insoma, Mogadon, Nitrados, Nitrazadon, Ormodon, Paxadorm, Remnos, and Somnite
• Synonyms: 1, 3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one; 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-on; 7-Nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one; 7-Nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one; 7-Nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one; N-desmethylnimetazepam; Nitrazepamum [inn-latin]; NTZ; Nitrazepam; Nitrazepam; LA 1; Ro 4-5360; Benzalin; Calsmin; Dormicum; Eatan; Eunoctin; Imeson; Mogadan; Surem; Unisomnia; 1,3-Dihydro-7-nitro-5-(phenyl-d5)-2H-1,4-benzodiazepin-2-one; 7-Nitro-5-(phenyl-d5)-1,3-dihydro-2H-1,4-benzodiazepin-2-one; Benzalin-d5; Calsmin-d5; Eatan-d5; Eunoctin-d5; Mogadon-d5; Remnos-d5; Ro 4-5360-d5; Nitrazepam-d5; Mogadon; Remnos; Radedorm

Database IDs

• CAS Number: 136765-45-2; 146-22-5
• EC Number: 205-665-2
• MDL Number: MFCD00058577
• PubChem SID: 46505806; 160964833; 24897666
• PubChem CID: 4506
• ATC CODE: N05CD02
• CHEMBL: 13209
• Chemspider ID: 4350
• DrugBank ID: DB01595
• KEGG ID: D00531
• Unique Ingredient Identifier: 9CLV70W7HS
• Wikipedia Title: Nitrazepam

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.899601
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.5474064
• LogD (pH = 7.4): 2.54794
• Log P: 2.54796
• Molar Refractivity: 79.2159 cm^3
• Polarizability: 28.4949 Å^3
• Polar Surface Area: 87.28 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.95
• LOG S: -3.97
• Solubility (Water): 2.99e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; DMSO; Ethanol; Ethyl Acetate; Methanol
• Apperance: Tan Solid; Yellow Solid
• Melting Point: 217-2200C (dec.); 223-227°C
• Hydrophobicity(logP): 2.25 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: DF2450000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 53-94%
• Excretion: Renal
• Half Life: 16-38 hours
• Metabolism: Hepatic
• Legal Status: Schedule IV (International)
• Pregnancy Category: D (Australia); D (US)
• Mechanism of Action: Benzodiazepine receptor agonist

Product Information

• Application(s): Anticonvulsant; Hypnotic; Nitrazepam is a sedative used to treat insomnia; Nitrazepam is in the group of drugs known as benzodiazepines, a class of antidepressants, anti-panic agents, and muscle relaxants; Tranquilliser
• Empirical Formula (Hill Notation): C15H11N3O3

DETAILS

DrugBank - DB01595

• Drug Groups: approved
• Description: A benzodiazepine derivative used as an anticonvulsant and hypnotic.
• Indication: Used to treat short-term sleeping problems (insomnia), such as difficulty falling asleep, frequent awakenings during the night, and early-morning awakening.
• Pharmacology: 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.
• Toxicity: Nitrazepam is a drug which is very frequently involved in drug intoxication, including overdose. Nitrazepam overdose may result in stereotypical symptoms of benzodiazepine overdose including intoxication, impaired balance, slurred speech. In cases of severe overdose this may progress to a comatose state with the possibility of death.
• Affected Organisms: Humans and other mammals
• Absorption: Bioavailability is 53-94% following oral administration.
• Half Life: 15-38 hours (mean elimination half life 26 hours).
• 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. [Pubmed] ; Robertson MD, Drummer OH: Postmortem drug metabolism by bacteria. J Forensic Sci. 1995 May;40(3):382-6. [Pubmed] ; Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Pubmed] ; 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. [Pubmed] ; 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. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - N3889

Biochem/physiol Actions
Hypnotic; ligand for the GABAA receptor benzodiazepine modulatory site.

Toronto Research Chemicals - N490140

Anticonvulsant; hypnotic.Controlled substance (depressant).

Toronto Research Chemicals - N490142

Anticonvulsant; hypnotic.Controlled substance (depressant).

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. Pubmed
• Robertson MD, Drummer OH: Postmortem drug metabolism by bacteria. J Forensic Sci. 1995 May;40(3):382-6. Pubmed
• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. Pubmed
• 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. Pubmed
• 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. Pubmed
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• Kangas, L., Acta Pharmacol. Toxicol., 45, 16 (1973)
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