CHEBI:7581 - nitrazepam

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ChEBI Name nitrazepam
ChEBI ID CHEBI:7581
Definition 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).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H11N3O3
Net Charge 0
Average Mass 281.26610
Monoisotopic Mass 281.080
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
SMILES [O-][N+](=O)c1ccc2NC(=O)CN=C(c3ccccc3)c2c1
Roles Classification
Biological Role(s): GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
(via benzodiazepine )
drug metabolite

Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
antispasmodic drug
A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.
GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
(via benzodiazepine )
sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nitrazepam (CHEBI:7581) has role anticonvulsant (CHEBI:35623)
nitrazepam (CHEBI:7581) has role antispasmodic drug (CHEBI:53784)
nitrazepam (CHEBI:7581) has role drug metabolite (CHEBI:49103)
nitrazepam (CHEBI:7581) has role GABA modulator (CHEBI:50268)
nitrazepam (CHEBI:7581) has role sedative (CHEBI:35717)
nitrazepam (CHEBI:7581) is a 1,4-benzodiazepinone (CHEBI:35500)
nitrazepam (CHEBI:7581) is a C-nitro compound (CHEBI:35716)
Incoming nimetazepam (CHEBI:31912) has functional parent nitrazepam (CHEBI:7581)
IUPAC Name
7-nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
INNs Sources
nitrazepam WHO MedNet
nitrazepam WHO MedNet
nitrazépam WHO MedNet
nitrazepamum WHO MedNet
Synonyms Sources
1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one NIST Chemistry WebBook
2,3-dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-one NIST Chemistry WebBook
7-nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one NIST Chemistry WebBook
7-nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one NIST Chemistry WebBook
N-desmethylnimetazepam NIST Chemistry WebBook
Ro 4-5360 ChemIDplus
Ro 5-3059 ChemIDplus
Brand Names Sources
Apodorm ChemIDplus
Atempol ChemIDplus
Benzalin ChemIDplus
Calsmin ChemIDplus
Dormicum ChemIDplus
Eatan ChemIDplus
Eunoctin ChemIDplus
Gerson ChemIDplus
Hipnax ChemIDplus
Hipsal ChemIDplus
Ibrovek ChemIDplus
Imeson ChemIDplus
Imesont ChemIDplus
Mogadon NIST Chemistry WebBook
Nelbon ChemIDplus
Nelmat ChemIDplus
Neozepam ChemIDplus
Neuchlonic ChemIDplus
Nitrados ChemIDplus
Paxisyn ChemIDplus
Pelson ChemIDplus
Persopit ChemIDplus
Radedorm ChemIDplus
Relact ChemIDplus
Remnos ChemIDplus
Somitran ChemIDplus
Sonebon ChemIDplus
Sonnolin ChemIDplus
Surem ChemIDplus
Trazenin ChemIDplus
Unisomnia ChemIDplus
Database Links Databases
C07487 KEGG COMPOUND
D00531 KEGG DRUG
DB01595 DrugBank
HMDB15534 HMDB
LSM-5681 LINCS
Nitrazepam Wikipedia
US3121076 Patent
View more database links
Registry Numbers Types Sources
146-22-5 CAS Registry Number NIST Chemistry WebBook
146-22-5 CAS Registry Number ChemIDplus
757185 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10030438 PubMed citation Europe PMC
15637997 PubMed citation Europe PMC
18603831 PubMed citation Europe PMC
19557123 PubMed citation Europe PMC
23085494 PubMed citation Europe PMC
23245766 PubMed citation Europe PMC
331868 PubMed citation Europe PMC
578380 PubMed citation Europe PMC
6143468 PubMed citation Europe PMC
6926838 PubMed citation Europe PMC
6988458 PubMed citation Europe PMC
7037262 PubMed citation Europe PMC
Last Modified
25 February 2016