CAS 146-22-5|CAS 136765-45-2|Calsamin|Benzalin|Cerson|Sonebon tofraniln a|Radedorm|Hipsal|Megadon|Sonebon|Insomin|Eunoctin|Somnite|Nelbon|Gerson|Somnibel|Ibrovek|Ipersed|7-Nitro-5-phenyl-1,3-dihydro...

General Information

Structure

Molecular Formula

C₁₅H₁₁N₃O₃

Molecular Mass

281.26614

Exact Mass

281.08004123

Charge

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

Canonic Smiles

O=C1CN=C(c2c(N1)ccc(c2)[N+](=O)[O-])c1ccccc1

Isomeric Smiles

O=C1Nc2c(C(=NC1)c1ccccc1)cc([N+](=O)[O-])cc2

Calculated Properties

JChem

LogD (pH = 7.4)

2.55

LogD (pH = 5.5)

2.55

Log P

2.55

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.71

Polar Surface Area

84.60

Polarizability

27.62

Molar Refractivity

78.21

LOG S

-4.30

Data Source

Names and Identifiers

Brand Name

BenzalinEunoctinSonnolinHipnaxInsominSomniteRelactHipsalIbrovekNeuchlonicRemnosSonebonEpinelbonMegadonIpersedMogadonEpibenzalinGersonSonebon tofraniln aRadedormPacisynNelbonSuremSomnibelCersonSandoz nitrazepamNitrazepam-10CalsaminCalsminTrazeninPaxisynAlodormNeozepamNoctesedMogadanImesonImesontMagadonNitradosApodormMogadonePelsonSomitranNitrempaxNitravetDumolidUnisomniaDormin-5EatanEunoktinApo-nitrazepam tablets BPNitrenpaxDormicumSomnasedMitidinAtempolDormo-purenEatan nNelmatNitrazadonPersopitNitrazepam-5LA 1 (VAN)Alodorm, Arem, Insoma, Mogadon, Nitrados, Nitrazadon, Ormodon, Paxadorm, Remnos, and Somnite

Synonyms

1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-oneNitrazepam7-Nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one2,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-on1, 3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-oneNTZ7-Nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-oneN-desmethylnimetazepamNitrazepamum [inn-latin]7-Nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-oneNitrazepam1,3-Dihydro-7-nitro-5-(phenyl-d5)-2H-1,4-benzodiazepin-2-oneEunoctin-d5Nitrazepam-d5Ro 4-5360-d5Calsmin-d57-Nitro-5-(phenyl-d5)-1,3-dihydro-2H-1,4-benzodiazepin-2-oneMogadon-d5Benzalin-d5Eatan-d5Remnos-d5RemnosMogadonRadedormEatanMogadanSuremImesonDormicumCalsminUnisomniaEunoctinLA 1Ro 4-5360BenzalinRo 5-3059nitrazepam7-nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one7-nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-oneN-desmethylnimetazepamRo 4-53602,3-dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-one

IUPAC Traditional name

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

IUPAC name

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

International Nonproprietary Name (INN)

nitrazepamnitrazepamum

Names and Identifiers

Registration numbers

EC Number

205-665-2

PubChem SID

2489766616096483346505806223440386

MDL Number

CAS Number

PubChem CID

Chemspider ID

ATC CODE

CHEMBL

DrugBank ID

Wikipedia Title

KEGG ID

Unique Ingredient Identifier

9CLV70W7HS

PubMed Citation Links

2308549461434687037262186038315783802324576633186810030438156379976926838698845819557123

CHEBI ID

CHEBI:7581

MetaboLights Database

Reaxys Registry

ACToR Database

BindingDB Database

BKMS React Database

NMRShiftDB Database

HMDB Database

BRENDA Database

Patent number

LINCS Database

BRENDA Ligand Database

34568

Drug Central Database

CompTox Database

KEGG DRUG Database

SureChEMBL Database

Registration numbers

Properties

Product Information

Empirical Formula (Hill Notation)

C15H11N3O3

Certificate of Analysis

Download link

Application(s)

Nitrazepam is a sedative used to treat insomnia

Hypnotic

Anticonvulsant

Nitrazepam is in the group of drugs known as benzodiazepines, a class of antidepressants, anti-panic agents, and muscle relaxants

Tranquilliser

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

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Molecule 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]

Wikipedia

Nitrazepam

Sigma Aldrich

N3889

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

TRC

N490142

Anticonvulsant; hypnotic.Controlled substance (depressant).

N490140

Anticonvulsant; hypnotic.Controlled substance (depressant).

ChEBI

CHEBI:7581

A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one which is substituted at positions 5 and 7 by phenyl and nitro groups, respectively. It is used as a hypnotic for the short-term management of insomnia and for the treatment of epileptic spasms in infants (West's syndrome).

Molecule Details

References

PubChem Literature

From Data Sources

• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. 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

• 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

• 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

• Robertson MD, Drummer OH: Postmortem drug metabolism by bacteria. J Forensic Sci. 1995 May;40(3):382-6. Pubmed

• Aboul-Enein, H.Y., et al.: Anal. Profiles Drug Subs., 9, 487 (1980).

• Kangas, L., Acta Pharmacol. Toxicol., 45, 16 (1973)

• Rieder, et al.: Arzneim.-Forsch., 23, 212 (1973)

• Aboul-Enein, H.Y., et al.: Anal. Profiles Drug Subs., 9, 487 (1973)

• Rieder, et al.: Arzneim.-Forsch., 23, 212 (1973)

• Kangas, L., Acta Pharmacol. Toxicol., 45, 16 (1973)

• Killam, E.K. et al., Adv. Neurol., 1980, 27, 597, (rev, pharmacol)

• Benzodiazepines, Current Concepts, Biological, Clinical and Social Perspectives, eds. Hindmarch, I. et al, J. Wiley, 1990, (book)

• Haran, R. et al., J. Het. Chem., 1980, 17, 1483, (pmr, cmr)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 3435, (synonyms)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 606

• Gilli, G. et al., Acta Cryst. B, 1977, 33, 2664, (cryst struct)

• Aboul-Enein, H.Y. et al., Anal. Profiles Drug Subst., 1980, 9, 487, (rev)

• Clarke, G.M. et al., J. Chem. Res., Synop., 1980, 400, (synth)

• Baruzzi, A. et al., Antiepileptic Drugs, (Eds. Levy, R. et al), Raven Press, New York, 1989, 785

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DLY000

• Sternbach, L.H. et al., J. Med. Chem., 1963, 6, 261

• Rieder, J. et al., Arzneim.-Forsch., 1973, 23, 212, (metab)

• Hannoun, M. et al., J. Het. Chem., 1981, 18, 963, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity