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Flumazenil

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Also known as AnexateFlumazepilLanexatMaziconNSC-759193RO-151788RO-151788000RO-1722RomaziconSID11111184SID11114035SID11532958SID26719655SID26752173SID50104818SID85231047SID90341071SID56422177SID104171157

Summary

Flumazenil (CHEMBL407) is an approved small-molecule GABA antagonist (ATC V03AB25) targeting GABRA1, GABRA2, and GABRA3; indicated across 11 conditions including obsessive-compulsive disorder and drug dependence.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: V03AB25
  • Targets: 6 (GABRA1, GABRA2, GABRA3…)
  • Indications: 11 conditions
  • Clinical trials: 25
  • Chemistry: 303.29 Da · C15H14FN3O3

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL407
NameFlumazenil
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID3373
ChEBICHEBI:5103
ATCV03AB25
Molecular formulaC15H14FN3O3
Molecular weight303.29
InChIKeyOFBIFZUFASYYRE-UHFFFAOYSA-N

SMILES: CCOC(=O)C1=C2CN(C(=O)C3=C(N2C=N1)C=CC(=C3)F)C

IUPAC name: ethyl 8-fluoro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

ChEBI 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.

Pharmacological roles (ChEBI): GABA antagonist, antidote to benzodiazepine poisoning.

Also known as: Anexate, Flumazenil, Flumazepil, Lanexat, Mazicon, NSC-759193, RO-151788, RO-151788000, RO-1722, Romazicon, flumazenil, SID11111184

Parent form; salt/anhydrous children: CHEMBL5400970, CHEMBL5413203

Patent coverage: 1,898 distinct patent families (7,150 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 7,050 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
GABRA1GABAA receptor α1 subunitAntagonist9.10%P14867
GABRA2GABAA receptor α2 subunit9.050%P47869
GABRA3GABAA receptor α3 subunit8.980%P34903
GABRA4GABAA receptor α4 subunitPositive7.030%P48169
GABRA5GABAA receptor α5 subunit9.220.9%P31644
GABRA6GABAA receptor α6 subunitPartial agonist6.830.1%Q16445

Broader ChEMBL bioactivity targets: 31 (assay-derived). Sample: Nuclear receptor ROR-gamma, Survival motor neuron protein, 4’-phosphopantetheinyl transferase ffp, Endonuclease 4, GABA-A receptor; anion channel, Gamma-aminobutyric acid receptor subunit alpha-1, Thyrotropin receptor, Menin/Histone-lysine N-methyltransferase MLL, GABA-A receptor; anion channel, GABA-A receptor; anion channel.

Bioactivity

ChEMBL activities: 58 potent at pChembl ≥ 5 of 62 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
P0821910.05Ki0.09nMCHEMBL_ACT_953846
P082199.42Ki0.38nMCHEMBL_ACT_1009128
GABRG29.35Kd0.45nMCHEMBL_ACT_12662655
GABRA59.3Kd0.5nMCHEMBL_ACT_2461360
P185089.3Ki0.5nMCHEMBL_ACT_311587
P082199.3IC500.5nMCHEMBL_ACT_867542
P185089.22Ki0.6nMCHEMBL_ACT_311588
GABRG29.22Ki0.6nMCHEMBL_ACT_60185
GABRG29.22Ki0.6nMCHEMBL_ACT_605780
GABRA59.2Ki0.63nMCHEMBL_ACT_23282400
O090289.1Ki0.8nMCHEMBL_ACT_176800
GABRA19.1Ki0.79nMCHEMBL_ACT_23282401
GABRA29.1Ki0.79nMCHEMBL_ACT_23282402
O090289.1Ki0.8nMCHEMBL_ACT_258931
GABRA19.1Ki0.8nMCHEMBL_ACT_60182
GABRA19.1Ki0.8nMCHEMBL_ACT_605777
O090289.1Ki0.8nMCHEMBL_ACT_672060
GABRP9.05Ki0.9nMCHEMBL_ACT_1505240
P082199.05Ki0.9nMCHEMBL_ACT_1700853
GABRG29.05Ki0.9nMCHEMBL_ACT_60183
GABRG29.05Ki0.9nMCHEMBL_ACT_605778
GABRP9.05Ki0.9nMCHEMBL_ACT_821054
P082199.05Ki0.9nMCHEMBL_ACT_881259
P082199.05Ki0.9nMCHEMBL_ACT_928399
GABRA39Ki1nMCHEMBL_ACT_23282403
GABRG28.98Ki1.05nMCHEMBL_ACT_60184
GABRG28.96Ki1.1nMCHEMBL_ACT_605779
O090288.92Ki1.2nMCHEMBL_ACT_681623
O090288.74IC501.82nMCHEMBL_ACT_571815
O090288.71Ki1.94nMCHEMBL_ACT_442055

Target pathways

Aggregated over 6 target gene(s): GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6.

Top Reactome pathways

2 total, by targets touching each:

PathwayTargetsGenes
GABA receptor activation6GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
Signaling by ERBB41GABRA1

Dominant GO biological processes

GO termTargets
gamma-aminobutyric acid signaling pathway6
synaptic transmission, GABAergic6
chloride transmembrane transport6
inhibitory synapse assembly6
monoatomic ion transport6
chloride transport6
monoatomic ion transmembrane transport6
regulation of postsynaptic membrane potential6
regulation of presynaptic membrane potential2
signal transduction2
central nervous system development1
behavioral fear response1
associative learning1
inner ear receptor cell development1
innervation1

Indications & clinical

Indications

11 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
obsessive-compulsive disorder2MONDO:0008114EFO:0004242
drug dependence2MONDO:0005303EFO:0003890
alcohol abuse2MONDO:0002046MONDO:0007079
insomnia1MONDO:0013600EFO:0004698
anxiety1MONDO:0011918EFO:0005230
narcolepsy1MONDO:0021107MONDO:0021107
idiopathic hypersomnia1MONDO:0018044MONDO:0018044
Parkinson disease1MONDO:0005180MONDO:0005180
fragile X syndrome1MONDO:0010383MONDO:0010383
hypersomnia1MONDO:0005466EFO:0005246

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 25.

Phase distribution

PhaseTrials
Not specified8
PHASE1/PHASE25
PHASE44
PHASE13
PHASE22
EARLY_PHASE12
PHASE2/PHASE31

Top trials by phase / activity

NCTPhaseStatusTitle
NCT02899156PHASE4TERMINATEDFlumazenil for Hypoactive Delirium Secondary to Benzodiazepine Exposure
NCT05468671PHASE4COMPLETEDClinical Application Value of Remazolam Combined With Sugammadex Sodium in Anesthesia for Endotracheal Surgery Under Bronchoscopy
NCT05681377PHASE4COMPLETEDImpact of Flumazenil on the Emergence Delirium
NCT06513923PHASE4COMPLETEDComparison of Remimazolam and Propofol on Emergence in Elderly Orthopedic Patients Under General Anesthesia
NCT00262639PHASE2/PHASE3COMPLETEDPrometa Protocol for Alcohol Dependence
NCT00000246PHASE2COMPLETEDRapid Benzodiazepine Detoxification Using Flumazenil - 1
NCT00695630PHASE1/PHASE2COMPLETEDFlumazenil Reversal of Oral Triazolam
NCT00997087PHASE2TERMINATEDA Randomized, Double-Blind, Placebo-Controlled Trial of Flumazenil for the Treatment of Obsessive Compulsive Disorder
NCT01071889PHASE1/PHASE2COMPLETEDSafety and the Efficacy of a Sublingual Administration of Flumazenil to Reverse the Effect of Hypnotic Drugs in Healthy Adults
NCT01183312PHASE1/PHASE2COMPLETEDFlumazenil for the Treatment of Primary Hypersomnia
NCT02048969PHASE1/PHASE2WITHDRAWNTreatment of Hepatic Encephalopathy With Flumazenil and Change in Cortical GABA Levels in MRS
NCT03462641PHASE1/PHASE2COMPLETEDModulation of GABA-A Receptors in Parkinson Disease-Flumazenil Arm
NCT06531369PHASE1NOT_YET_RECRUITINGFlumazenil Antagonism of Remimazolam in Kidney Transplant Patients
NCT00681746PHASE1COMPLETEDPositron Emission Tomography (PET) Study With (11C) Flumazenil to Determine Central GABAA Receptor Occupancy of AZD6280
NCT01655914PHASE1COMPLETEDSafety and Pharmacokinetic Study of Sublingual Flumazenil (CRLS035) in Healthy Adults
NCT06205719EARLY_PHASE1NOT_YET_RECRUITINGEffect of Remazolam on Anesthesia Recovery in Patients Undergoing Fundus Surgery
NCT03743805EARLY_PHASE1WITHDRAWNRapid Reversal of CNS-Depressant Drug Effect Prior to Brain Death Determination
NCT05939674Not specifiedRECRUITINGEffects of Flumazenil on Recovery After Total Intravenous Anesthesia With Remimazolam
NCT02157428Not specifiedCOMPLETEDEffect of Flumazenil on Recovery From General Anesthesia With Isoflurane
NCT02690389Not specifiedCOMPLETEDElectro-acupuncture and Flumazenil’s Effect on Sedation
NCT04329585Not specifiedUNKNOWNGABA Antagonist to Improve Reversal of Anesthesia With High-density EEG Surveillance
NCT05382806Not specifiedCOMPLETEDReversal of Remimazolam by a Single Dose of Flumazenil
NCT05397886Not specifiedCOMPLETEDComparison of Remimazolam With Flumazenil vs. Propofol During RFCA for Atrial Fibrillation
NCT05435911Not specifiedCOMPLETEDComparison of Recovery From General Anesthesia in Remimazolam With Flumazenil vs. Propofol
NCT06563063Not specifiedCOMPLETEDFinding ED90 of Flumazenil for Selective Improvement of Respiratory Distress by Remimazolam

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

81 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
APALUTAMIDEChEMBL + PubChemPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
CLONAZEPAMChEMBL + PubChemPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
DIAZEPAMChEMBL + PubChemPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
ENZALUTAMIDEChEMBL + PubChemPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
BREXANOLONEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
GANAXOLONEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
LIOTHYRONINEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
PROPOFOLChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
ALFAXALONEChEMBL + PubChemPhase 2 (approved)GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
ABECARNILChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
BAICALEINChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
DELORAZEPAMChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
FLAVONEChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
PROGABIDEChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA4, GABRA5, GABRA6
BRETAZENILChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5, GABRA6
ALPRAZOLAMChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
CHLORDIAZEPOXIDEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
ESZOPICLONEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA4
FLUNITRAZEPAMChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
TRIAZOLAMChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
AZD7325ChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
BASMISANILChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
MK-0777ChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
ZOLPIDEMChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3
DARIGABATChEMBLPhase 2GABRA1, GABRA3, GABRA5
PANADIPLONChEMBLPhase 2GABRA1, GABRA3, GABRA6
CRIZOTINIBChEMBL + PubChemPhase 4 (approved)GABRA1, GABRA2
ASENAPINEChEMBLPhase 4 (approved)GABRA1, GABRA2
AZELASTINEChEMBLPhase 4 (approved)GABRA1, GABRA2
BENPERIDOLChEMBLPhase 4 (approved)GABRA1, GABRA2
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)GABRA1, GABRA2
CHLORAMBUCILChEMBLPhase 4 (approved)GABRA1, GABRA2
CLOZAPINEChEMBLPhase 4 (approved)GABRA1, GABRA2
EPINASTINEChEMBLPhase 4 (approved)GABRA1, GABRA2
ETOMIDATEChEMBLPhase 4 (approved)GABRA1, GABRA2
GLAFENINEChEMBLPhase 4 (approved)GABRA1, GABRA2
LINDANEChEMBLPhase 4 (approved)GABRA1, GABRA6
SIMVASTATINChEMBLPhase 4 (approved)GABRA1, GABRA2
TIPRANAVIRChEMBLPhase 4 (approved)GABRA1, GABRA2
TROGLITAZONEChEMBLPhase 4 (approved)GABRA1, GABRA2
ZALEPLONChEMBLPhase 4 (approved)GABRA1, GABRA2
ZURANOLONEChEMBLPhase 4 (approved)GABRA1, GABRA4
SURAMINChEMBLPhase 3GABRA1, GABRA2
TIRATRICOLChEMBLPhase 3GABRA1, GABRA2
SARIPIDEMChEMBLPhase 2GABRA1, GABRA5
ZOTEPINEChEMBLPhase 2GABRA1, GABRA2
.gamma.-aminobutyric acidPubChemApprovedGABRA4, GABRA6
AfatinibPubChemApprovedGABRA1, GABRA2
ApixabanPubChemApprovedGABRA1, GABRA2
BinimetinibPubChemApprovedGABRA1, GABRA2
CaffeinePubChemApprovedGABRA4, GABRA6
chenodiolPubChemApprovedGABRA1, GABRA2
CiprofloxacinPubChemApprovedGABRA4, GABRA6
FipronilPubChemApprovedGABRA4, GABRA6
FulvestrantPubChemApprovedGABRA1, GABRA2
gentian violetPubChemApprovedGABRA1, GABRA2
ImipenemPubChemApprovedGABRA1, GABRA2
LactulosePubChemApprovedGABRA1, GABRA2
levocarnitinePubChemApprovedGABRA1, GABRA2
PhenytoinPubChemApprovedGABRA4, GABRA6

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot