diazepam   Click here for help

GtoPdb Ligand ID: 3364

Synonyms: Diastat® | LA-III | Valium® | WY-3467
Approved drug PDB Ligand
diazepam is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Diazepam is a benzodiazepine drug with long acting anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties.
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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

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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 3
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 32.67
Molecular weight 284.07
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 Clc1ccc2c(c1)C(=NCC(=O)N2C)c1ccccc1
Isomeric SMILES Clc1ccc2c(c1)C(=NCC(=O)N2C)c1ccccc1
InChI InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
InChI Key AAOVKJBEBIDNHE-UHFFFAOYSA-N
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
CYP3A4 2
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRH1 receptor Rn Antagonist Antagonist 5.2 pKi - 1
⤷ pKi 5.2 (Ki 7.1x10-6 M) [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 α1 subunit Primary target of this compound Hs Allosteric modulator Positive 7.8 pKi - 4
⤷ pKi 7.8 (Ki 1.63x10-8 M) [Binds to: benzodiazepine site] [4]
Description: Assay using recombinant GABAA channels with subunit composition; α1β1γ2.
GABAA receptor α2 subunit Primary target of this compound Hs Allosteric modulator Positive 7.8 pKi - 4
⤷ pKi 7.8 (Ki 1.69x10-8 M) [Binds to: benzodiazepine site] [4]
Description: Assay using recombinant GABAA channels with subunit composition; α2β1γ2.
GABAA receptor α3 subunit Primary target of this compound Hs Allosteric modulator Positive 7.8 pKi - 4
⤷ pKi 7.8 (Ki 1.7x10-8 M) [Binds to: benzodiazepine site] [4]
Description: Assay using recombinant GABAA channels with subunit composition; α3β1γ2.
Targets where the ligand is described in the comment field
Target Comment
GABAA receptor α6 subunit Diazepam and flunitrazepam are not active at channels containing this subunit. Zn2+ is an endogenous allosteric regulator and causes potent inhibition of receptors formed from binary combinations of α and β subunits, incorporation of a δ or γ subunit causes a modest, or pronounced, reduction in inhibitory potency, respectively [3]. [3H]Ro154513 selectively labels α6-subunit and α4-subunit-containing receptors in the presence of a saturating concentration of a 'classical' benzodiazepine (e.g. diazepam). Sieghart et al. (2022) provides a review of the pharmacology of α6-containing GABAA receptors.
GABAA receptor α4 subunit Diazepam and flunitrazepam are not active at this subunit. Zn2+ is an endogenous allosteric regulator and causes potent inhibition of receptors formed from binary combinations of α and β subunits, incorporation of a δ or γ subunit causes a modest, or pronounced, reduction in inhibitory potency, respectively [3]. [3H]Ro154513 labels α4βγ2 and α6βγ2 receptors in the presence of a saturating concentration of a 'classical' benzodiazepine (e.g. diazepam).
Ligand mentioned in the following text fields
GABAA receptors overview