ChemFOnt: Showing chemical card for Nitrazepam (CFc000009796)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:02 UTC

Chemfont ID

CFc000009796

Molecule Identification

Common Name

Nitrazepam

Definition

Nitrazepam is only found in individuals that have used or taken this drug. It is a benzodiazepine derivative used as an anticonvulsant and hypnotic.Nitrazepam belongs to a group of medicines called benzodiazepines. It acts on benzodiazepine receptors in the brain which are associated with the GABA receptors causing an enhanced binding of GABA (gamma amino butyric acid) to GABAA receptors. GABA is a major inhibitory neurotransmitter in the brain, involved in inducing sleepiness, muscular relaxation and control of anxiety and fits, and slows down the central nervous system. The anticonvulsant properties of nitrazepam and other benzodiazepines may be in part or entirely due to binding to voltage-dependent sodium channels rather than benzodiazepine receptors. Sustained repetitive firing seems to be limited by benzodiazepines effect of slowing recovery of sodium channels from inactivation.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one	ChEBI
2,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-one	ChEBI
7-Nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one	ChEBI
7-Nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one	ChEBI
Apodorm	ChEBI
Atempol	ChEBI
Benzalin	ChEBI
Calsmin	ChEBI
Dormicum	ChEBI
Eatan	ChEBI
Eunoctin	ChEBI
Gerson	ChEBI
Hipnax	ChEBI
Hipsal	ChEBI
Ibrovek	ChEBI
Imeson	ChEBI
Imesont	ChEBI
Mogadon	ChEBI
N-Desmethylnimetazepam	ChEBI
Nelbon	ChEBI
Nelmat	ChEBI
Neozepam	ChEBI
Neuchlonic	ChEBI
Nitrados	ChEBI
Nitrazepamum	ChEBI
Paxisyn	ChEBI
Pelson	ChEBI
Persopit	ChEBI
Radedorm	ChEBI
Relact	ChEBI
Remnos	ChEBI
Ro 4-5360	ChEBI
Ro 5-3059	ChEBI
Somitran	ChEBI
Sonebon	ChEBI
Sonnolin	ChEBI
Surem	ChEBI
Trazenin	ChEBI
Unisomnia	ChEBI
1, 3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one	HMDB
2,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-ON	HMDB
7-Nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one	HMDB
Alter brand OF nitrazepam	HMDB
CSP Brand OF nitrazepam	HMDB
DDSA brand OF nitrazepam	HMDB
Desitin brand OF nitrazepam	HMDB
Nitrazepam al	HMDB
Nitrazepam-neuraxpharm	HMDB
Nitrodiazepam	HMDB
Novanox	HMDB
Taurus brand OF nitrazepam	HMDB
CT-Arzneimittel brand OF nitrazepam	HMDB
Aliud brand OF nitrazepam	HMDB
Alphapharma brand OF nitrazepam	HMDB
Dormicum brand OF nitrazepam	HMDB
Nitrazadon	HMDB
Nitrazep	HMDB
Norgine brand OF nitrazepam	HMDB
Rhoxalpharma brand OF nitrazepam	HMDB
Scheurich brand OF nitrazepam	HMDB
Serenade	HMDB
Dermatech brand OF nitrazepam	HMDB
ICN brand OF nitrazepam	HMDB
Imadorm	HMDB
Pfleger brand OF nitrazepam	HMDB
Rhoxal-nitrazepam	HMDB
Wernigerode brand OF nitrazepam	HMDB
Allphar brand OF nitrazepam	HMDB
Alodorm	HMDB
Alpharma brand OF nitrazepam	HMDB
Dormalon	HMDB
Dormo-puren	HMDB
Protea brand OF nitrazepam	HMDB
Somnite	HMDB
United drug brand OF nitrazepam	HMDB
Neuraxpharm brand OF nitrazepam	HMDB
Rhoxal nitrazepam	HMDB
Nitrazepam neuraxpharm	HMDB

Chemical Formula

C₁₅H₁₁N₃O₃

Average Molecular Weight

281.2661

Monoisotopic Molecular Weight

281.080041233

IUPAC Name

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

Traditional Name

gerson

CAS Registry Number

146-22-5

SMILES

[O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2)C=C1

InChI Identifier

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)

InChI Key

KJONHKAYOJNZEC-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Nitroaromatic compound
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Ketimine
Lactam
C-nitro compound
Organic nitro compound
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Imine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic zwitterion
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-nitro compound (CHEBI:7581 )
1,4-benzodiazepinone (CHEBI:7581 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015534)

Source

Exogenous

Exogenous (HMDB: HMDB0015534)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0015534)
Sedative (HMDB: HMDB0015534)

Pharmaceutical industry

Antispasmodic drug (HMDB: HMDB0015534)

Biological role

Modulator

GABA modulator (HMDB: HMDB0015534)

Drug metabolite (HMDB: HMDB0015534)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon