BRETAZENIL

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H20BrN3O3
Molecular Weight	418.284
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCCN1C(=O)C3=C(Br)C=CC=C3N4C=NC(C(=O)OC(C)(C)C)=C24

InChI

InChIKey=LWUDDYHYYNNIQI-ZDUSSCGKSA-N

InChI=1S/C19H20BrN3O3/c1-19(2,3)26-18(25)15-16-13-8-5-9-22(13)17(24)14-11(20)6-4-7-12(14)23(16)10-21-15/h4,6-7,10,13H,5,8-9H2,1-3H3/t13-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H20BrN3O3
Molecular Weight	418.284
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18791060 | http://adisinsight.springer.com/drugs/800000640

Bretazenil (Ro 16-6028) is a partial agonist at the GABAA benzodiazepine site. It displayed anticonvulsive activity and was in phase III of a clinical trial in Switzerland to treat Anxiety disorders. But that study was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; benzodiazepine site 38 Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11920931	Partial Agonist 290

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1324584	Primary		Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Changes in benzodiazepine-receptor activity modify morphine withdrawal syndrome in mice.	1992 Aug	1327709
Cloning of cDNAs encoding the human gamma-aminobutyric acid type A receptor alpha 6 subunit and characterization of the pharmacology of alpha 6-containing receptors.	1996 Feb	8632757
Functional pharmacology of GABA(A) receptors containing the chicken brain gamma 4 subunit.	2001 May 4	11348623
Isobolographic analysis of chlordiazepoxide and triazolam combinations in squirrel monkeys discriminating triazolam.	2001 Nov	11702092
Role of the histidine residue at position 105 in the human alpha 5 containing GABA(A) receptor on the affinity and efficacy of benzodiazepine site ligands.	2002 Jan	11786501
Mechanism-based pharmacodynamic modeling of the interaction of midazolam, bretazenil, and zolpidem with ethanol.	2002 Jun	12449497
5-ethoxymethyl-7-fluoro-3-oxo-1,2,3,5-tetrahydrobenzo[4,5]imidazo[1,2a]pyridine-4-N-(2-fluorophenyl)carboxamide (RWJ-51204), a new nonbenzodiazepine anxiolytic.	2002 Nov	12388665
Neonatal development of the rat visual cortex: synaptic function of GABAA receptor alpha subunits.	2002 Nov 15	12433958
A rapid punishment procedure for detection of anxiolytic compounds in mice.	2004 Feb	14504684
Anxioselective anxiolytics: can less be more?	2004 Oct 1	15464051
Comparison of the behavioral effects of bretazenil and flumazenil in triazolam-dependent and non-dependent baboons.	2005 Sep 5	16129429
Differential behavioral effects of low efficacy positive GABAA modulators in combination with benzodiazepines and a neuroactive steroid in rhesus monkeys.	2006 Feb	16331290
Decreases in nestlet shredding of mice by serotonin uptake inhibitors: comparison with marble burying.	2006 Mar 20	16182315
Contribution of specific binding to the central benzodiazepine site to the brain concentrations of two novel benzodiazepine site ligands.	2007 Sep	17570124
Varenicline in the treatment of tobacco dependence.	2008 Apr	18728741
Comparison of the novel subtype-selective GABAA receptor-positive allosteric modulator NS11394 [3'-[5-(1-hydroxy-1-methyl-ethyl)-benzoimidazol-1-yl]-biphenyl-2-carbonitrile] with diazepam, zolpidem, bretazenil, and gaboxadol in rat models of inflammatory and neuropathic pain.	2008 Dec	18791060
Loss of GABAergic signaling by AgRP neurons to the parabrachial nucleus leads to starvation.	2009 Jun 26	19563755
Interneurons, GABAA currents, and subunit composition of the GABAA receptor in type I and type II cortical dysplasia.	2010 Jul	20618425
Anticonvulsant, anxiolytic, and non-sedating actions of imidazenil and other imidazo-benzodiazepine carboxamide derivatives.	2010 Jun	20227434
The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes.	2010 Jun 25	20303942

Sample Use Guides

In Vivo Use Guide

Influence of oral administration of 1 mg bretazenil on the sleep EEG and the concomitant nocturnal secretion of cortisol, growth hormone and prolactin in ten healthy young men

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:17:15 UTC 2023` Edited by `admin` on `Fri Dec 15 16:17:15 UTC 2023`
Record UNII	OSZ0E9DGOJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BRETAZENIL

Official Name

English

bretazenil [INN]

Common Name

English

RO-166028000

Code

English

BRETAZENIL [USAN]

Common Name

English

RO 16-6028/000

Code

English

9H-IMIDAZO(1,5-A)PYRROLO(2,1-C)(1,4)BENZODIAZEPINE-1-CARBOXYLIC ACID, 8-BROMO-11,12,13,13A-TETRAHYDRO-9-OXO-, 1,1-DIMETHYLETHYL ESTER, (S)-

Common Name

English

tert-Butyl (S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

Common Name

English

RO-F61816-6028/000

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C28197