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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Click here for structure editor
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/)
References
1. Anfuso CD, Olivieri M, Fidilio A, Lupo G, Rusciano D, Pezzino S, Gagliano C, Drago F, Bucolo C. (2017)
Gabapentin Attenuates Ocular Inflammation: In vitro and In vivo Studies.
Front Pharmacol, 8: 173. [PMID:28420991]
2. Brown JP, Dissanayake VU, Briggs AR, Milic MR, Gee NS. (1998)
Isolation of the [3H]gabapentin-binding protein/alpha 2 delta Ca2+ channel subunit from porcine brain: development of a radioligand binding assay for alpha 2 delta subunits using [3H]leucine.
Anal Biochem, 255 (2): 236-43. [PMID:9451509]
3. Dooley DJ, Donovan CM, Pugsley TA. (2000)
Stimulus-dependent modulation of [(3)H]norepinephrine release from rat neocortical slices by gabapentin and pregabalin.
J Pharmacol Exp Ther, 295 (3): 1086-93. [PMID:11082444]
4. Dooley DJ, Mieske CA, Borosky SA. (2000)
Inhibition of K(+)-evoked glutamate release from rat neocortical and hippocampal slices by gabapentin.
Neurosci Lett, 280 (2): 107-10. [PMID:10686389]
5. Gee NS, Brown JP, Dissanayake VU, Offord J, Thurlow R, Woodruff GN. (1996)
The novel anticonvulsant drug, gabapentin (Neurontin), binds to the alpha2delta subunit of a calcium channel.
J Biol Chem, 271 (10): 5768-76. [PMID:8621444]
6. Hendrich J, Van Minh AT, Heblich F, Nieto-Rostro M, Watschinger K, Striessnig J, Wratten J, Davies A, Dolphin AC. (2008)
Pharmacological disruption of calcium channel trafficking by the alpha2delta ligand gabapentin.
Proc Natl Acad Sci USA, 105 (9): 3628-33. [PMID:18299583]
7. Maneuf YP, Hughes J, McKnight AT. (2001)
Gabapentin inhibits the substance P-facilitated K(+)-evoked release of [(3)H]glutamate from rat caudial trigeminal nucleus slices.
Pain, 93 (2): 191-6. [PMID:11427331]
8. Manville RW, Abbott GW. (2018)
Gabapentin Is a Potent Activator of KCNQ3 and KCNQ5 Potassium Channels.
Mol Pharmacol, 94 (4): 1155-1163. [PMID:30021858]
9. Meleine M, Boudieu L, Gelot A, Muller E, Lashermes A, Matricon J, Silberberg C, Theodorou V, Eschalier A, Ardid D et al.. (2016)
Comparative effects of α2δ-1 ligands in mouse models of colonic hypersensitivity.
World J Gastroenterol, 22 (31): 7111-23. [PMID:27610021]
10. Mortell KH, Anderson DJ, Lynch 3rd JJ, Nelson SL, Sarris K, McDonald H, Sabet R, Baker S, Honore P, Lee CH et al.. (2006)
Structure-activity relationships of alpha-amino acid ligands for the alpha2delta subunit of voltage-gated calcium channels.
Bioorg Med Chem Lett, 16 (5): 1138-41. [PMID:16380257]