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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Partial Agonist 290

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267	Primary		Phase III 656	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
5 ng/mL	0.5 mg single, sublingual		BRETAZENIL plasma	Homo sapiens
5.4 ng/mL	0.5 mg single, sublingual	ALCOHOL	BRETAZENIL plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
17.6 ng × h/mL	0.5 mg single, sublingual		BRETAZENIL plasma	Homo sapiens
19.2 ng × h/mL	0.5 mg single, sublingual	ALCOHOL	BRETAZENIL plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.2 h	0.5 mg single, sublingual		BRETAZENIL plasma	Homo sapiens
2.3 h	0.5 mg single, sublingual	ALCOHOL	BRETAZENIL plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
18 mg 1 times / day multiple, oral Studied dose	unhealthy, ADULT	Disc. AE: Tiredness, Insomnia... Other AEs: Dizziness, Headache...

Showing 1 to 1 of 1 entries

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AEs

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AE	Significance	Dose	Population
Aggressiveness	1.5%	18 mg 1 times / day multiple, oral Studied dose	unhealthy, ADULT
Weight gain	1.5%	18 mg 1 times / day multiple, oral Studied dose	unhealthy, ADULT
Insomnia	1.5% Disc. AE	18 mg 1 times / day multiple, oral Studied dose	unhealthy, ADULT
Tiredness	1.5% Disc. AE	18 mg 1 times / day multiple, oral Studied dose	unhealthy, ADULT
Headache	3%	18 mg 1 times / day multiple, oral Studied dose	unhealthy, ADULT

Showing 1 to 5 of 6 entries

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PubMed

PubMed

Show entries

Title	Date	PubMed
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
Anxioselective compounds acting at the GABA(A) receptor benzodiazepine binding site.	2003 Aug	12871032
Mechanism-based pharmacokinetic/pharmacodynamic modeling of the electroencephalogram effects of GABAA receptor modulators: in vitro-in vivo correlations.	2003 Jan	12490579
Comparative cue generalization profiles of L-838, 417, SL651498, zolpidem, CL218,872, ocinaplon, bretazenil, zopiclone, and various benzodiazepines in chlordiazepoxide and zolpidem drug discrimination.	2006 Mar	16339395
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

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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
Record UNII	OSZ0E9DGOJ
Record Status	`Validated (UNII)`
Record Version

Show entries

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

Showing 1 to 5 of 8 entries

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Classification Tree

Code System

Code

Agent Affecting Nervous System

NCI_THESAURUS

C28197

Agent Affecting Nervous System

NCI_THESAURUS

C264

Showing 1 to 2 of 2 entries

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Code System

Code

Type

Description

NCI_THESAURUS

C72111

PRIMARY

EPA CompTox

DTXSID6046266

PRIMARY

INN

6319

PRIMARY

USAN

DD-21

PRIMARY

MESH

C054626

PRIMARY

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Related Record

Type

Details


					OSZ0E9DGOJ

BRETAZENIL

ACTIVE MOIETY

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

PubMed

Sample Use Guides

C_max

T_1/2