Flumazenil (CHEM016715)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:41:16 UTC
Update Date2016-11-09 01:15:27 UTC
Accession NumberCHEM016715
Identification
Common NameFlumazenil
ClassSmall Molecule
DescriptionFumazenil is an imidazobenzodiazepine derivative and a potent benzodiazepine receptor antagonist that competitively inhibits the activity at the benzodiazepine recognition site on the GABA/benzodiazepine receptor complex, thereby reversing the effects of benzodiazepine on the central nervous system.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AnexateChEBI
FlumazeniloChEBI
FlumazenilumChEBI
LanexatChEBI
RomaziconKegg
Anexic acidGenerator
Hoffman-la roche brand OF flumazenilHMDB
FlumazepilHMDB
Roche brand OF flumazenilHMDB
Hoffman la roche brand OF flumazenilHMDB
Chemical FormulaC15H14FN3O3
Average Molecular Mass303.288 g/mol
Monoisotopic Mass303.102 g/mol
CAS Registry Number78755-81-4
IUPAC Nameethyl 12-fluoro-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,11,13-pentaene-5-carboxylate
Traditional Nameflumazenil
SMILESCCOC(=O)C1=C2CN(C)C(=O)C3=C(C=CC(F)=C3)N2C=N1
InChI IdentifierInChI=1S/C15H14FN3O3/c1-3-22-15(21)13-12-7-18(2)14(20)10-6-9(16)4-5-11(10)19(12)8-17-13/h4-6,8H,3,7H2,1-2H3
InChI KeyOFBIFZUFASYYRE-UHFFFAOYSA-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 fluoride
  • Aryl halide
  • Benzenoid
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary carboxylic acid amide
  • Imidazole
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organofluoride
  • Organic oxygen compound
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility1.04 g/LALOGPS
logP1.54ALOGPS
logP0.33ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)3.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area64.43 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.93 m³·mol⁻¹ChemAxon
Polarizability29.97 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-3490000000-d0d0177798f08c7ec17aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0lg0-3890000000-2453b74fd469fb228589Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kdi-1293000000-7a192ee695af1d78e7bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kdi-0193000000-a02a88da5dbc9ae8b8a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0lg0-3890000000-2453b74fd469fb228589Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0pxr-0290000000-d4bd11c45454f089d4e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0039000000-512256f7d9c74da3dba9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-2094000000-2d484b39bd1b420cc821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4950000000-0e25df1f3bb12b6672c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-2098000000-b0cd088a553670984014Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-2092000000-d4159177fc35a792370aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a71-3790000000-b679dafe637ef0296213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-ea5ff0185619f28dfa79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-0095000000-53b3b234fff80e66c40aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-055r-0390000000-e81718d47d5a3874b74bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-a44687b430e97e86bb72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-0093000000-3aaa035c9d0947af6126Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-0290000000-06260a3ca1602bf6180fSpectrum
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 IDDB01205
HMDB IDHMDB0015336
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFlumazenil
Chemspider ID3256
ChEBI ID5103
PubChem Compound ID3373
Kegg Compound IDC07825
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ngo AS, Anthony CR, Samuel M, Wong E, Ponampalam R: Should a benzodiazepine antagonist be used in unconscious patients presenting to the emergency department? Resuscitation. 2007 Jul;74(1):27-37. Epub 2007 Feb 15.
2. Olkkola KT, Ahonen J: Midazolam and other benzodiazepines. Handb Exp Pharmacol. 2008;(182):335-60. doi: 10.1007/978-3-540-74806-9_16.
3. Maeda S, Miyawaki T, Higuchi H, Shimada M: Effect of flumazenil on disturbance of equilibrium function induced by midazolam. Anesth Prog. 2008 Fall;55(3):73-7. doi: 10.2344/0003-3006-55.3.73.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11881583
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23126253
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23431889
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24563235
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26324010
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26469689