Bretazenil

• Catalog Number: ACM84379135
• Product Name: Bretazenil
• CAS: 84379-13-5
• Category: Agonists
• Description: Bretazenil, also known as Ro 16-6028, is GABA A receptor agonist potentially for the treatment of anxiety disorders. Bretazenil differs from traditional 1,4-benzodiazepines by being a partial agonist and because it binds to α1, α2, α3, α4, α5 and α6 subunit containing GABAA receptor benzodiazepine receptor complexes. 1,4-benzodiazepines bind only to α1, α2, α3 and α5 GABAA benzodiazepine receptor complexes.
• Synonyms: Ro 16-6028; Ro 16 6028; Ro16-6028; Ro 166028; Ro 166028; Ro166028; Ro 16-6028/000; Bretazenil
• IUPAC Name: tert-butyl (S)-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
• Molecular Weight: 418.29
• Molecular Formula: C19H20BrN3O3
• Canonical SMILES: O=C(C1=C([C@@]2([H])N3CCC2)N(C=N1)C4=CC=CC(Br)=C4C3=O)OC(C)(C)C
• 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
• InChI Key: LWUDDYHYYNNIQI-ZDUSSCGKSA-N
• Flash Point: 313.2ºC
• Density: 1.56 g/cm³
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Shelf Life: >2 years if stored properly
• Storage: Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
• Biological Target: Bretazenil is a partial agonist at the GABAA benzodiazepine site (EC50 = 10 nM at α1β1γ2 receptors).
• Drug Formulation: This drug may be formulated in DMSO
• Elemental Analysis: C, 54.56; H, 4.82; Br, 19.10; N, 10.05; O, 11.47
• Exact Mass: 417.0688
• HS Tariff Code: 2934.99.9001
• In Vitro Activity: The differences in intrinsic activity and receptor subtype specificity of the newly developed benzodiazepine receptor ligands bretazenil, divaplon and abecarnil were assessed in recombinant gamma-aminobutyric acidA (GABAA) receptors expressed in mammalian cells. Bretazenil displayed an intrinsic activity which amounted only to 58 +/- 7% and 35 +/- 11% of that of flunitrazepam at the alpha 3 beta 2 gamma 2 and alpha 5 beta 2 gamma 2 combination, respectively. Thus, the partial agonism postulated for bretazenil and divaplon on pharmacological grounds is shown to be operative on the level of single GABAA receptors.; Reference: J Pharmacol Exp Ther. 1993 Jul;266(1):385-91. https://pubmed.ncbi.nlm.nih.gov/8392559/
• In Vivo Activity: Alzet minipumps were loaded with bretazenil, a GABAA receptor partial agonist, and implanted subcutaneously to deliver 750 ng/hr for 14 days. After 3 baseline days with the bretazenil-eluting minipump, the AgrpDTR/+ mice were treated with DT (diptheria toxin). Food consumption by the bretazenil-treated group fell for the first 6 days after DT treatment, but then also returned to normal over the next 12 days. Bretazenil (0.2 mg/kg, ip) increased food consumption by wild-type mice during the first 4 hr, but 24-hr food intake was normal. Chronic delivery of bretazenil to wild-type animals for 10 days via a minipump had no effect on body weight. Once-daily administration of bretazenil (0.2 mg/kg, ip) was ineffective at preventing starvation after AgRP neuron ablation, suggesting that chronic activation of GABAA receptors is an important aspect of the rescue strategy. Chronic treatment with bretazenil also restored intra-oral sucrose consumption to >80% of original after ablation of AgRP neurons. Thus, both consummatory and appetitive responses are rescued by bretazenil treatment after AgRP neuron ablation.; Reference: Cell. 2009 Jun 26;137(7):1225-34. https://pubmed.ncbi.nlm.nih.gov/19563755/
• LogP: 3.81870
• PSA: 64.43
• Refractive Index: 1.685
• Shipping: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
• Stock Solution Storage: 0-4 °C for short term (days to weeks), or -20 °C for long term (months).
• Storage Conditions: 2-8ºC