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

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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 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 2
Rotatable bonds 3
Topological polar surface area 63.32
Molecular weight 171.13
XLogP 1.39
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 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
No information available.
Summary of Clinical Use Click here for help
Gabapentin is used as an adjunctive therapy in epilepsy and is also widely used to treat neuralgic/neuropathic pain. A gabapentin prodrug, gabapentin enacarbil, is approved to treat restless leg syndrome and post-herpetic neuralgia.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Gabapentin is a voltage-gated calcium channel modulator which acts via a cascade involving GABA receptors, to reduce the release of monoamine neurotransmitters including norepinephrine, substance P, and glutamate [3-4,7], potentially in the CA1 area of the hippocampus. Specific, high-affinity binding sites for gabapentin have been isolated from pig and mouse neuronal tissue [2,5,10] and rabbit and rat skeletal muscle [5]. This binding has been attributed to the α2δ subunit (CACNA2D1, P54289) of the VGCC, indicating that at least some of gabapentin's clinical effects are due to interaction with this calcium channel subunit. Some evidence exists to support the hypothesis that compounds such as gabapentin and pregabalin don't actually block presynaptic calcium channels, but rather exert an inhibitory effect on the re-cycling of the channels from endosomal pools back to the plasma membrane via interaction with intracellular δ subunits [6].