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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2D Structure
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Physico-chemical Properties
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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
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InChI InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
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]