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
No information available.
Summary of Clinical Use
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
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].