flumazenil   Click here for help

GtoPdb Ligand ID: 4192

Synonyms: Anexate® | Ro15-1788
Approved drug PDB Ligand
flumazenil is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Flumazenil reverses the effects of benzodiazepine sedatives.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

flumazenil is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
GABAA receptor α5 subunit Primary target of this compound Hs Allosteric modulator - 9.2 pKi - 3
⤷ pKi 9.2 (Ki 6x10-10 M) [Binds to: benzodiazepine site] Antagonist at α1 receptors, but allosteric modulator at other subtypes. [3]
Description: Affinity measured using α5β3γ2 receptors.
GABAA receptor α1 subunit Primary target of this compound Hs Allosteric modulator Antagonist 9.1 pKi - 3
⤷ pKi 9.1 (Ki 8x10-10 M) [Binds to: benzodiazepine site] Antagonist at α1 receptors, but allosteric modulator at other subtypes. [3]
Description: Affinity measured using α1β3γ2 receptors.
GABAA receptor α2 subunit Primary target of this compound Hs Allosteric modulator - 9.1 pKi - 3
⤷ pKi 9.1 (Ki 9x10-10 M) [Binds to: benzodiazepine site] Antagonist at α1 receptors, but allosteric modulator at other subtypes. [3]
Description: Affinity measured using α2β3γ2 receptors.
GABAA receptor α3 subunit Primary target of this compound Hs Allosteric modulator - 9.0 pKi - 2-3
⤷ pKi 9.0 (Ki 1.05x10-9 M) [Binds to: benzodiazepine site] Antagonist at α1 receptors, but allosteric modulator at other subtypes. [2-3]
Description: Affinity measured using α3β3γ2 receptors.
GABAA receptor α4 subunit Rn Allosteric modulator Positive 7.0 pKi - 4
⤷ pKi 7.0 (Ki 9.4x10-8 M) Antagonist at α1 receptors, but allosteric modulator at other subtypes. [4]
Description: Antagonism of complexes containing α4β2γ2 subunits heterologously expressed in vitro.
GABAA receptor α6 subunit Hs Allosteric modulator Partial agonist 6.8 pKi - 3
⤷ pKi 6.8 (Ki 1.48x10-7 M) [Binds to: benzodiazepine site] low affinity [3]
Description: Affinity measured using α6β3γ2 receptors.