Flumazenil

Flumazenil (also known as flumazepil, code name Ro 15-1788) is a selective GABAA receptor antagonist administered via injection, otic insertion, or intranasally. Therapeutically, it acts as both an antagonist and antidote to benzodiazepines (particularly in cases of overdose), through competitive inhibition.

Flumazenil
Clinical data
Trade namesAnexate, Lanexat, Mazicon, Romazicon
Other namesethyl 8-fluoro- 5,6-dihydro- 5-methyl- 6-oxo- 4H- imidazo [1,5-a] [1,4] benzodiazepine- 3-carboxylate
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: B3
Routes of
administration		IV
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismHepatic
Elimination half-life7–15 min (initial)
20–30 min (brain)
40–80 min (terminal)
ExcretionUrine 90–95%
Feces 5–10%
Identifiers
  • Ethyl 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.128.069
Chemical and physical data
FormulaC15H14FN3O3
Molar mass303.293 g·mol−1
3D model (JSmol)
SMILES
  • Fc(c1)ccc-2c1C(=O)N(C)Cc3n2cnc3C(=O)OCC
  • 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 Y
  • Key:OFBIFZUFASYYRE-UHFFFAOYSA-N Y
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It was first characterized in 1981, and was first marketed in 1987 by Hoffmann-La Roche under the trade name Anexate. However, it did not receive FDA approval until December 20, 1991. The developer lost its exclusive patent rights in 2008; so at present, generic formulations of this drug are available. Intravenous flumazenil is primarily used to treat benzodiazepine overdoses and to help reverse anesthesia. Administration of flumazenil by sublingual lozenge and topical cream has also been tested.

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