Compound Detail

CHEMBL407

FLUMAZENIL

💊 Approved Drug

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💊 Approved Drug

CCOC(=O)c1ncn2c1CN(C)C(=O)c1cc(F)ccc1-2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL407
Name	FLUMAZENIL
Phase	Approved
Structure Type	MOL
InChI Key	OFBIFZUFASYYRE-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Anexate Flumazenil Flumazepil Lanexat Mazicon NSC-759193 RO 15-1788/000 RO-15-1788 RO-15-1788/000 RO-151788 RO-151788000 RO-1722 +2 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

303.3

MW (Da)

1.77

ALogP

HBA

HBD

64.4

PSA (Å²)

0.79

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1991
Availability	Prescription
Chirality	Achiral

Routes of Administration

Parenteral

Flags

Black Box Warning

USAN Stem	-azenil
USAN Year	1987

Extended Properties

Molecular Formula	C15H14FN3O3
MW	303.29
Aromatic Rings	2
Heavy Atoms	22
NP-Likeness	-0.63

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
GABA-A receptor; anion channel allosteric antagonist	ALLOSTERIC ANTAGONIST	GABA-A receptor; anion channel	✓	✓

Indications

Alcoholism Obsessive-Compulsive Disorder Substance-Related Disorders Anxiety Dental Anxiety Disorders of Excessive Somnolence Fragile X Syndrome Idiopathic Hypersomnia Narcolepsy Parkinson Disease Sleep Initiation and Maintenance Disorders

ATC Classification

V03AB25

flumazenil

Level 1: VARIOUS

Level 2: ALL OTHER THERAPEUTIC PRODUCTS

Drug Warnings

Black Box Warning

neurotoxicity

Country: United States

Activity Summary

Ki 79 meas. best 10.05

IC50 5 meas. best 9.3

Kd 3 meas. best 9.35

EC50 1 meas. best 7.52

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
GABA-A receptor; anion channel CHEMBL2094107	Ki	10.05	9.324	0.1	5
Unchecked CHEMBL612545	Ki	9.72	8.515	0.2	36
GABA-A receptor; alpha-3/beta-3/gamma-2 CHEMBL2094120	Kd	9.35	9.35	0.5	1
Gamma-aminobutyric acid receptor subunit alpha-5 CHEMBL5112	Kd	9.3	9.3	0.5	1
GABA-A receptor; anion channel CHEMBL2094107	IC50	9.3	9.3	0.5	1
GABA-A receptor; alpha-1/beta-2/gamma-2 CHEMBL2095167	Ki	9.3	8.135	0.5	2
GABA A receptor alpha-3/beta-2/gamma-2 CHEMBL2111343	Ki	9.22	9.22	0.6	1
GABA-A receptor; alpha-5/beta-3/gamma-2 CHEMBL2094122	Ki	9.22	9.22	0.6	2
Gamma-aminobutyric acid receptor subunit alpha-5 CHEMBL5112	Ki	9.2	9.2	0.6	1
GABA-A receptor; anion channel CHEMBL1907607	Ki	9.1	8.3611	0.8	9
Gamma-aminobutyric acid receptor subunit alpha-2 CHEMBL4956	Ki	9.1	9.1	0.8	1
GABA-A receptor; alpha-1/beta-3/gamma-2 CHEMBL2094121	Ki	9.1	9.1	0.8	2
Gamma-aminobutyric acid receptor subunit alpha-1 CHEMBL1962	Ki	9.1	8.79	0.8	2
GABA-A receptor; alpha-2/beta-3/gamma-2 CHEMBL2094130	Ki	9.05	9.05	0.9	2
GABA-A receptor; anion channel CHEMBL2093872	Ki	9.05	9.05	0.9	2
Gamma-aminobutyric acid receptor subunit alpha-3 CHEMBL3026	Ki	9.0	9.0	1.0	1
GABA-A receptor; alpha-3/beta-3/gamma-2 CHEMBL2094120	Ki	8.98	8.97	1.1	2
GABA-A receptor; anion channel CHEMBL1907607	IC50	8.74	8.58	1.8	2
Gamma-aminobutyric acid receptor subunit alpha-4 CHEMBL2472	Ki	8.7	8.7	2.0	1
Gamma-aminobutyric acid receptor subunit alpha-1 CHEMBL1962	Kd	8.7	8.7	2.0	1
Unchecked CHEMBL612545	IC50	8.64	8.525	2.3	2
GABA A receptor alpha-2/beta-2/gamma-2 CHEMBL2111413	Ki	8.24	8.24	5.7	1
GABA A receptor alpha-3/beta-2/gamma-2 CHEMBL2111339	Ki	8.09	8.09	8.1	1
GABA A receptor alpha-6/beta-2/gamma-2 CHEMBL2111365	Ki	7.82	7.578	15.0	5
Unchecked CHEMBL612545	EC50	7.52	7.52	30.0	1
GABA-A receptor; alpha-6/beta-3/gamma-2 CHEMBL2095190	Ki	6.83	6.83	148.0	2
Gamma-aminobutyric acid receptor subunit alpha-6 CHEMBL2579	Ki	6.8	6.8	158.5	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	16.0	mL.min-1.kg-1	Homo sapiens
CL	16.0	mL.min-1.kg-1	Homo sapiens
CL	16.0	mL.min-1.kg-1	Homo sapiens
CL	16.0	mL.min-1.kg-1	Homo sapiens
CL	10.6	mL.min-1.g-1	Homo sapiens
Cmax	1120.0	nM	Homo sapiens
F	20.0	%	Homo sapiens
Fu	0.5	-	Homo sapiens
Fu	0.58	-	Homo sapiens
Fu	0.58	-	Homo sapiens
MRT	1.0	hr	Homo sapiens
T1/2	0.78	hr	Homo sapiens
T1/2	0.6	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
GABA-A receptor; anion channel	Ki	=	0.09	nM	10.05	Displacement of [3H]- Ro.15-1788 from GABA-A central Benzodiazepine receptor (Bz...	10633040
Unchecked	Ki	=	0.19	nM	9.72	Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha-1 ...	18973287
GABA-A receptor; anion channel	Ki	=	0.38	nM	9.42	In vitro inhibition of [3H]flunitrazepam binding to GABA-A benzodiazepine recept...	1319492
GABA-A receptor; alpha-3/beta-3/gamma-2	Kd	=	0.45	nM	9.35	Binding affinity to human GABAA alpha3beta2gamma2 expressed in thymidine kinase-...	23121096
Unchecked	Ki	=	0.5	nM	9.3	Binding affinity for rat GABA-A receptor alpha-5--beta-2-gamma-2 subunits expres...	7799410
GABA-A receptor; alpha-1/beta-2/gamma-2	Ki	=	0.5	nM	9.3	Binding affinity for rat GABA-A receptor alpha-1-beta-2-gamma-2 subunits express...	7799410
Gamma-aminobutyric acid receptor subunit alpha-5	Kd	=	0.5	nM	9.3	Binding affinity to GABAA alpha-5-beta-2-gamma-2 receptor	18537233
GABA-A receptor; anion channel	IC50	=	0.5	nM	9.3	Affinity to displace [3H]flunitrazepam from Benzodiazepine receptor in bovine br...	2167984
GABA-A receptor; alpha-5/beta-3/gamma-2	Ki	=	0.6	nM	9.22	Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor...	10633039
GABA-A receptor; alpha-5/beta-3/gamma-2	Ki	=	0.6	nM	9.22	Binding affinity for Gamma-aminobutyric acid A receptor alpha-5-beta-3-gamma-2	9767648
GABA A receptor alpha-3/beta-2/gamma-2	Ki	=	0.6	nM	9.22	Binding affinity for rat GABA-A receptor alpha-3-beta-2-gamma-2 subunits express...	7799410
Unchecked	Ki	=	0.6	nM	9.22	Binding affinity for mutant rat GABA-A receptor alpha-4-(his)-beta-2-gamma-2 sub...	7799410
Unchecked	Ki	=	0.6	nM	9.22	Binding affinity to rat chimeric GABA-A receptor C6, alpha1-alpha6 chimeric subu...	7799410
Gamma-aminobutyric acid receptor subunit alpha-5	Ki	=	0.631	nM	9.2	Binding affinity to GABBA alpha5 (unknown origin)	32870011
GABA-A receptor; anion channel	Ki	=	0.8	nM	9.1	Binding affinity against Diazepam sensitive (DS) Gamma-aminobutyric acid A recep...	7752192
GABA-A receptor; anion channel	Ki	=	0.8	nM	9.1	Binding affinity for Diazepam sensitive (DS) isoform of the benzodiazepine (Bz) ...	8390574
GABA-A receptor; anion channel	Ki	=	0.8	nM	9.1	Binding affinity for Diazepam-Sensitive fraction of GABA-A benzodiazepine recept...	8386769
GABA-A receptor; alpha-1/beta-3/gamma-2	Ki	=	0.8	nM	9.1	Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor...	10633039
GABA-A receptor; alpha-1/beta-3/gamma-2	Ki	=	0.8	nM	9.1	Binding affinity against alpha-1-beta-3-gamma-2 GABAA/BzR receptor subtype.	9767648
Gamma-aminobutyric acid receptor subunit alpha-1	Ki	=	0.7943	nM	9.1	Binding affinity to GABBA alpha1 (unknown origin)	32870011

Literature References

PubMed	DOI	Target Context	# Activities
18973287	10.1021/jm800889m	Unchecked	47
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
-	10.6019/CHEMBL4689842	HEK-293T	10
-	10.6019/CHEMBL4689842	U2OS	9
12477354	10.1021/jm020944u	Mus musculus	8
20070106	10.1021/jm901371v	Homo sapiens	8
-	10.6019/CHEMBL4689842	Fibroblast	7
17626010	10.1074/jbc.m702153200	Unchecked	6
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
-	10.6019/CHEMBL5209801	Adhesion G-protein coupled receptor F1	5
-	10.6019/CHEMBL5209801	Glucose-dependent insulinotropic receptor	5
-	10.6019/CHEMBL5209801	Free fatty acid receptor 4	5
-	10.6019/CHEMBL5209801	Glucagon-like peptide 1 receptor	5
-	10.6019/CHEMBL5209801	Sphingosine 1-phosphate receptor 1	5
7799410	10.1021/jm00052a019	GABA A receptor alpha-6/beta-2/gamma-2	5
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	5
-	10.6019/CHEMBL5209801	Alpha-2A adrenergic receptor	5
26982523	10.1021/acs.jmedchem.6b00034	Unchecked	5
21751815	10.1021/jm2001597	Unchecked	5

Data from ChEMBL 36 via Core Engine