Ligand id: 5483

Name: gabapentin

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View more information in the IUPHAR Pharmacology Education Project: gabapentin

Structure and Physico-chemical Properties

2D Structure
Calculated 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

Molecular properties generated using the CDK

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 Pharmacol8: 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. U.S.A.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.
Pain93 (2): 191-6. [PMID:11427331]
8. 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]
9. 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]