Flumazenil

Flumazenil
Clinical data
Trade names	Anexate, others
Other names	ethyl 8-fluoro- 5,6-dihydro- 5-methyl- 6-oxo- 4H- imidazo [1,5-a] [1,4] benzodiazepine- 3-carboxylate, RO 15-1788
AHFS/Drugs.com	Monograph
License data	US DailyMed: Flumazenil;
Pregnancy; category	AU: B3;
Routes of; administration	Intranasal, intravenous
ATC code	V03AB25 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Liver
Elimination half-life	7–15 min (initial) ; 20–30 min (brain) ; 40–80 min (terminal)
Excretion	Urine 90–95% ; Feces 5–10%
Identifiers
	IUPAC name Ethyl 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate;
CAS Number	78755-81-4 ;
PubChem CID	3373;
IUPHAR/BPS	4192;
DrugBank	DB01205 ;
ChemSpider	3256 ;
UNII	40P7XK9392;
KEGG	D00697 ;
ChEBI	CHEBI:5103 ;
ChEMBL	ChEMBL407 ;
CompTox Dashboard (EPA)	DTXSID2023064 ;
ECHA InfoCard	100.128.069
Chemical and physical data
Formula	C15H14FN3O3
Molar mass	303.293 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Fc(c1)ccc-2c1C(=O)N(C)Cc3n2cnc3C(=O)OCC;
	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 ; Key:OFBIFZUFASYYRE-UHFFFAOYSA-N ;
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Flumazenil, also known as flumazepil, is a selective GABA_A 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.

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 1991. The developer lost its exclusive patent rights in 2008 and generic formulations 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.