gabapentin   Click here for help

GtoPdb Ligand ID: 5483

Synonyms: CI 945 | Go 3450 | GOE 2450 | GOE 3450 | Neurontin®
Approved drug PDB Ligand Immunopharmacology Ligand
gabapentin is an approved drug (FDA (1993))
Compound class: Synthetic organic
Comment: Although gabapentin was desigened to mimic gamma-aminobutyric acid (GABA), it is believed that gabapentinoids act on different brain receptors, such as the α2δ subunit of voltage-gated calcium channels.
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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

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: gabapentin

gabapentin 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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 2
Rotatable bonds 3
Topological polar surface area 63.32
Molecular weight 171.13
XLogP 1.39
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NCC1(CCCCC1)CC(=O)O
Isomeric SMILES NCC1(CCCCC1)CC(=O)O
InChI InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
InChI Key UGJMXCAKCUNAIE-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Bioactivity Comments
Gabapentin inhibits binding of [3H]gabapentin to the pig brain VGCC α2δ subunit with an IC50 of 50nM [5] and inhibits [3H]L-leucine interaction with the mouse homologue with an IC50 of 120nM [10]. Gabapentin has a Kd of 29nM at the α2δ subunit isolated from rat skeletal muscle [5]. However, we have been unable to find publicly available bioactivity data for this drug at its proposed human molecular target(s) to substantiate its MMOA, and have therefore not tagged a primary drug target.
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kv7.5 Hs Activator Activation 8.7 pEC50 - 8
⤷ pEC50 8.7 (EC50 1.9x10-9 M) [8]
Kv7.3 Hs Activator Activation 8.3 pEC50 - 8
⤷ pEC50 8.3 (EC50 5.3x10-9 M) [8]
Ligand mentioned in the following text fields
Voltage-gated calcium channels (CaV) overview