CHEBI:5103 - flumazenil

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ChEBI Name flumazenil
ChEBI ID CHEBI:5103
Definition An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H14FN3O3
Net Charge 0
Average Mass 303.289
Monoisotopic Mass 303.102
InChI InChI=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
InChIKey OFBIFZUFASYYRE-UHFFFAOYSA-N
SMILES C1=NC(=C2N1C=3C(C(N(C2)C)=O)=CC(=CC3)F)C(OCC)=O
Roles Classification
Biological Role(s): GABA antagonist
A compound that inhibits the action of gamma-aminobutyric acid.
GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
(via benzodiazepine )
Application(s): GABA antagonist
A compound that inhibits the action of gamma-aminobutyric acid.
antidote to benzodiazepine poisoning
A role borne by a molecule that acts to counteract or neutralise the deleterious effects of benzodiazepines.
GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
(via benzodiazepine )
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ChEBI Ontology
Outgoing flumazenil (CHEBI:5103) has role antidote to benzodiazepine poisoning (CHEBI:90757)
flumazenil (CHEBI:5103) has role GABA antagonist (CHEBI:65259)
flumazenil (CHEBI:5103) is a ethyl ester (CHEBI:23990)
flumazenil (CHEBI:5103) is a imidazobenzodiazepine (CHEBI:142118)
flumazenil (CHEBI:5103) is a organofluorine compound (CHEBI:37143)
IUPAC Name
ethyl 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate
INNs Sources
flumazenil ChemIDplus
flumazenilo ChemIDplus
flumazenilum ChemIDplus
Brand Names Sources
Anexate DrugBank
Lanexat DrugBank
Manual Xrefs Databases
1195 DrugCentral
C07825 KEGG COMPOUND
D00697 KEGG DRUG
DB01205 DrugBank
Flumazenil Wikipedia
HMDB0015336 HMDB
LSM-4228 LINCS
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Registry Numbers Types Sources
4763661 Beilstein Registry Number Beilstein
4763661 Reaxys Registry Number Reaxys
78755-81-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11881583 PubMed citation Europe PMC
23126253 PubMed citation Europe PMC
23431889 PubMed citation Europe PMC
24563235 PubMed citation Europe PMC
26324010 PubMed citation Europe PMC
26469689 PubMed citation Europe PMC
Last Modified
05 September 2018