gabapentin   

GtoPdb Ligand ID: 5483

Synonyms: CI 945 | Go 3450 | GOE 2450 | GOE 3450 | Neurontin®
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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2D Structure
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Physico-chemical Properties
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
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
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
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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