flumazenil   

GtoPdb Ligand ID: 4192

Synonyms: Anexate® | Ro15-1788
flumazenil is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Flumazenil reverses the effects of benzodiazepine sedatives.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 63.91
Molecular weight 303.1
XLogP 2.92
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCOC(=O)c1ncn2c1CN(C)C(=O)c1c2ccc(c1)F
Isomeric SMILES CCOC(=O)c1ncn2c1CN(C)C(=O)c1c2ccc(c1)F
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
InChI Key OFBIFZUFASYYRE-UHFFFAOYSA-N
Bioactivity Comments
Flumazenil is non-selective in action, but is most potent at GABAA receptors containing the α1, α3 and α5 subunits [1].
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
GABAA receptor α5 subunit Hs Allosteric modulator Antagonist 9.2 pKi - 1
pKi 9.2 (Ki 6x10-10 M) [Binds to: benzodiazepine site] [1]
Description: Affinity measured using α5β3γ2 receptors.
GABAA receptor α1 subunit Hs Allosteric modulator Antagonist 9.1 pKi - 1
pKi 9.1 (Ki 8x10-10 M) [Binds to: benzodiazepine site] [1]
Description: Affinity measured using α1β3γ2 receptors.
GABAA receptor α2 subunit Hs Allosteric modulator Antagonist 9.1 pKi - 1
pKi 9.1 (Ki 9x10-10 M) [Binds to: benzodiazepine site] [1]
Description: Affinity measured using α2β3γ2 receptors.
GABAA receptor α3 subunit Hs Allosteric modulator Antagonist 9.0 pKi - 1
pKi 9.0 (Ki 1.05x10-9 M) [Binds to: benzodiazepine site] [1]
Description: Affinity measured using α3β3γ2 receptors.
GABAA receptor α4 subunit Rn Allosteric modulator Positive 7.0 pKi - 2
pKi 7.0 (Ki 9.4x10-8 M) [2]
Description: Antagonism of complexes containing α4β2γ2 subunits heterologously expressed in vitro.
GABAA receptor α6 subunit Hs Allosteric modulator Partial agonist 6.8 pKi - 1
pKi 6.8 (Ki 1.48x10-7 M) [Binds to: benzodiazepine site] low affinity [1]
Description: Affinity measured using α6β3γ2 receptors.