nitrazepam (CHEBI:7581)

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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

Average Mass

281.26610

Monoisotopic Mass

281.08004

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.

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

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

Last Modified

22 February 2017