Bretazenil (CHEM018884)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:37:37 UTC
Update Date2016-11-09 01:15:53 UTC
Accession NumberCHEM018884
Identification
Common NameBretazenil
ClassSmall Molecule
DescriptionBretazenil (Ro16-6028) is an imidazopyrrolobenzodiazepine anxiolytic drug which is derived from the benzodiazepine family, and was invented in 1988. It is most closely related in structure to the GABA antagonist flumazenil, although its effects are somewhat different. It is classified as a high-potency benzodiazepine due to its high affinity binding to benzodiazepine binding sites where it acts as a partial agonist. Its profile as a partial agonist and preclinical trial data suggests that it may have a reduced adverse effect profile. In particular bretazenil has been proposed to cause a less strong development of tolerance and withdrawal syndrome. 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.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
t-Butyl-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo(1,5-a)-pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylateMeSH
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-carboxylic acidGenerator
Chemical FormulaC19H20BrN3O3
Average Molecular Mass418.291 g/mol
Monoisotopic Mass417.069 g/mol
CAS Registry Number84379-13-5
IUPAC Nametert-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
Traditional Namebretazenil
SMILES[H][C@@]12CCCN1C(=O)C1=C(Br)C=CC=C1N1C=NC(C(=O)OC(C)(C)C)=C21
InChI IdentifierInChI=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 KeyLWUDDYHYYNNIQI-ZDUSSCGKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as imidazo[1,5-a][1,4]benzodiazepines. Imidazo[1,5-a][1,4]benzodiazepines are compounds containing an imidazole ring and a 1,4-benzodiazepine ring system, both sharing one nitrogen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct ParentImidazo[1,5-a][1,4]benzodiazepines
Alternative Parents
Substituents
  • Imidazo[1,5-a][1,4]benzodiazepine
  • Para-diazepine
  • Imidazole-4-carbonyl group
  • Aryl bromide
  • Aryl halide
  • N-substituted imidazole
  • Benzenoid
  • Azole
  • Imidazole
  • Pyrrolidine
  • Vinylogous amide
  • Vinylogous halide
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Carboxylic acid ester
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organobromide
  • Organic oxygen compound
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.05ALOGPS
logP3.18ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)3.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area64.43 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity111.6 m³·mol⁻¹ChemAxon
Polarizability39.86 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-1009800000-360f6aca058c1189d3d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02bf-5009100000-3e4af942887c0160c724Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i0-9153000000-fb12c4cbb0d70e2368e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-6006900000-60e9b60acdc8adf00c00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9004300000-7a2374799e8e38e1b17dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9021000000-fbb5518475510cbe3821Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBretazenil
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID107926
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available