ChemicalBook > CAS DataBase List > Bretazenil

Bretazenil

Product Name
Bretazenil
CAS No.
84379-13-5
Chemical Name
Bretazenil
Synonyms
BRETAZENIL;Brn 4765855;Bretazenilum;Unii-osz0E9dgoj;BRETAZENIL USP/EP/BP;Bretazenilum [inn-latin];9H-IMIDAZO(1,5-A)PYRROLO(2,1-C);1,1-dimethylethylester,(s)-13a-tetrahydro-8-bromo-9-oxo;9H-Imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid;9h-imidazo(1,5-a)pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylicacid,11,12,13,
CBNumber
CB6503200
Molecular Formula
C19H20BrN3O3
Formula Weight
418.28
MOL File
84379-13-5.mol
More
Less

Bretazenil Property

Boiling point:
594.3±50.0 °C(Predicted)
Density 
1.56±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: 24 mg/mL, soluble
form 
solid
pka
0.78±0.20(Predicted)
color 
white
InChI
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
InChIKey
LWUDDYHYYNNIQI-ZDUSSCGKSA-N
SMILES
N12C=NC(C(OC(C)(C)C)=O)=C1[C@]1([H])CCCN1C(=O)C1=C(Br)C=CC=C12
More
Less

Safety

Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
NJ5899850
More
Less

Hazard and Precautionary Statements (GHS)

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
B6434
Product name
Bretazenil
Purity
≥96% (HPLC), solid
Packaging
5mg
Price
$210
Updated
2024/03/01
Sigma-Aldrich
Product number
B6434
Product name
Bretazenil
Purity
≥96% (HPLC), solid
Packaging
25mg
Price
$937
Updated
2024/03/01
Cayman Chemical
Product number
28411
Product name
Bretazenil
Packaging
5mg
Price
$98
Updated
2024/03/01
Cayman Chemical
Product number
28411
Product name
Bretazenil
Packaging
25mg
Price
$310
Updated
2024/03/01
Cayman Chemical
Product number
28411
Product name
Bretazenil
Packaging
1mg
Price
$37
Updated
2024/03/01
More
Less

Bretazenil Chemical Properties,Usage,Production

Description

Bretazenil is an imidazobenzodiazepine partial agonist and a potent anxiolytic. It is rapidly absorbed and has a half-life of 2.5 hours. Animal work has shown that, even after long-term administration of bretazenil, there are no changes in GABA receptor binding or function, and tolerance does not occur. Studies in humans have also suggested that bretazenil has a low abuse potential (Sellers et al. 1991). In terms of clinical effects, bretazenil has demonstrated anxiolytic efficacy in both generalized anxiety disorder and panic disorder (Katschnig et al. 1991), but no controlled study has compared bretazenil with a classic full agonist.

Originator

Bretazenil,Hoffman-La Roche, Inc.

Uses

Anti-anxiety agent.
Bretazenil potentiated GABA responses on α4β3γ2 cells.
Bretazenil is a partial benzodiazepine receptor agonist. Benzodiazepines, mainly diazepam, are commonly used as anticonvulsants in the treatment of organophosphate casualties. Bretazenil has been used to determine non-specific binding due to its affinity to bind to a variety of γ-aminobutyric acid type A (GABAA) receptor subtypes (α1-3;5). It has also been used as a GABAA receptor partial agonist in the subcutaneous Alzet minipumps to treat obese agouti related protein (AgRP) ablated and lean naive mice to study its effect on them.

Therapeutic Function

Anxiolytic

Biological Activity

Bretazenil is a positive allosteric modulator of GABAA receptors with anticonvulsant and anxiolytic activity. It potentiates GABA-gated chloride currents in rat cortical neurons and in HEK293 cells expressing α1β1γ2 subunit-containing GABAA receptors (EC50s = 60 and 10 nM, respectively). Bretazenil inhibits binding of the benzodiazepine diazepam to rat cerebral cortex homogenates (IC50 = 2.2 nM). It inhibits tonic convulsions induced by pentylenetetrazol (PTZ; Item No. 18682) and maximal electroshock (MES) in rats (ED50s = 0.07 and 0.48 mg/kg, respectively). Bretazenil (5-30 mg/kg) increases the number of open arm entries and percentage of time spent in the open arms of the elevated plus maze in mice, indicating anxiolytic-like activity.

Pharmacology

Bretazenil exhibits an ticonflflict and anticonvulsant properties. Only mild sedation appears at doses needed to produce anticonvulsant or anxiolytic effects, and potentiation of ethanol-induced sedation is less pronounced than with diazepam.

storage

Desiccate at +4°C

Bretazenil Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Bretazenil Suppliers

More
Less

View Lastest Price from Bretazenil manufacturers

Dorne Chemical Technology co. LTD
Product
BRETAZENIL 84379-13-5
Price
US $10.00/ASSAYS
Min. Order
1ASSAYS
Purity
99%
Supply Ability
100kg
Release date
2024-03-26
Hebei Yanxi Chemical Co., Ltd.
Product
Bretazenil 84379-13-5
Price
US $40.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-09-18
Shandong Hanjiang Chemical Co., Ltd
Product
Bretazenil 84379-13-5
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10T
Release date
2024-01-25

84379-13-5, BretazenilRelated Search:


  • 9H-IMIDAZO(1,5-A)PYRROLO(2,1-C)(1,4)BENZODIAZEPINE-1-CARBOXYLIC ACID,11,12,13,13A-TTRRRAHYDRO-8-BROMO-9-OXO-,1,1-DIMETHYLETHYL ESTER,(S)-
  • 1,1-dimethylethylester,(s)-13a-tetrahydro-8-bromo-9-oxo
  • 9h-imidazo(1,5-a)pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylicacid,11,12,13,
  • (13aS)-8-Bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid tert-butyl ester
  • 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)-
  • Bretazenilum
  • Bretazenilum [inn-latin]
  • Brn 4765855
  • Unii-osz0E9dgoj
  • (13aS)-8-Bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylicacid1,1-dimethylethylester
  • 9H-Imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid
  • Ro 16-6028, 9H-Imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid
  • 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, (13aS)-
  • BRETAZENIL USP/EP/BP
  • 9H-IMIDAZO(1,5-A)PYRROLO(2,1-C)
  • BRETAZENIL
  • Inhibitor,site,Bretazenil,inhibit,γ-Aminobutyric acid Receptor,function,benzodiazepine,Gamma-aminobutyric acid Receptor,GABA Receptor,motoric,Ro 16-6028,anticonvulsant
  • (S)-tert-butyl 8-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a][1,4]diazepine-1-carboxylate
  • tert-butyl (7S)-14-bromo-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,?.0?,11]heptadeca-1(13),3,5,14,16-pentaene-5-carboxylate
  • 84379-13-5
  • C19H20N3O3Br
  • 84379-13-5