Bretazenil
Grundinformationen
- CAS
84379-13-5- Standard-SMILES
CC(C)(C)OC(=O)c1ncn2c1[C@@H]1CCCN1C(=O)c1c(Br)cccc1-2- InChIKey
LWUDDYHYYNNIQI-ZDUSSCGKSA-N- Summenformel
- C19H20BrN3O3
- Durchschnittliche Molmasse
- 418,3 g/mol
- Monoisotopische Masse
- 417,0688
Überblick
Bretazenil is a small molecule drug. The usage of the INN stem '-nil' in the name indicates that Bretazenil is a benzodiazepine receptor antagonist/agonist. Bretazenil has a monoisotopic molecular weight of 417.07 Da.
Namen und Bezeichner
- Bevorzugter Name
- Bretazenil
- IUPAC
- tert-butyl (7S)-14-bromo-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate
- Englischer Name
- Bretazenil
- Summenformel
- C19H20BrN3O3
- Molmasse
- 418.28
Namen und Synonyme
Bretazenil84379-13-5BretazenilumDTXSID6046266OSZ0E9DGOJBRN 4765855Ro 16-6028/000Ro-166028000DTXCID4026266RO-F61816-6028/000RefChem:917541t-butyl-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo(1,5-a)-pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylate
Weitere Namen anzeigen
Unii-osz0E9dgojBRETAZENIL USP/EP/BPBretazenilum [inn-latin]9H-IMIDAZO(1,5-A)PYRROLO(2,1-C)1,1-dimethylethylester,(s)-13a-tetrahydro-8-bromo-9-oxo9H-Imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid9h-imidazo(1,5-a)pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylicacid,11,12,13,
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)-Ro 16-6028Ro-16-6028CHEMBL366947tert-butyl (7S)-14-bromo-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylateNCGC00160640-019H-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)-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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,1
- Polarare Oberfläche (TPSA)
- 64,4 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 593
Experimentelle und physikochemische Eigenschaften
LogP2.48
Physikochemische Eigenschaften
- Siedepunkt
- 594.3 · 594.3±50.0 °C(Predicted)
- Dichte
- 1.56 · 1.56±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 24 mg/mL, · DMSO: 24 mg/mL, soluble
- Aggregatzustand
- solid
- pka
- 0.78 · 0.78±0.20(Predicted)
- Farbe
- 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
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- RTECS-Nr.
- NJ5899850
- safety_code
- 22-24/25
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
A 2025 publication comprehensively mapped the metabolic fate of bretazeni. It noted that bretazeni is a highly potent benzodiazepine with a short elimination half-life and the potential for rapid metabolism. A total of 26 metabolites were identified via a) bigh-resolution mass spectrometry and b) software-aided data processing of in vitro and in vivo samples. Eight of the metabolites were detected in vitro, 15 were detected in in postmortem urine, and 11 were detected in in postmortem blood. The authors recommended hydroxy-bretazenil, reduced hydroxy-bretazenil, and reduced dihydroxy-bretazenil as significant markers to detect bretazenil use.
MeSH Pharmacological ClassificationDrugs used to prevent SEIZURES or reduce their severity.
Absorption, Distribution and ExcretionA 2025 publication comprehensively mapped the metabolic fate of bretazeni, and noted that bretazenil has the potential for rapid metabolisma and has a short elimination half-life.
Anwendungen
BeschreibungBretazenil 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.
VerwendenAnti-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.
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