γ-Aminobutyric acid (GABA) is a major inhibitory neurotransmitter that functions by binding to the GABA receptors located in the spinal cord.1 Gabapentin (Neurontin®) is a GABA analogue that acts as an anticonvulsant with proven analgesic effects in various neuropathic pain syndromes such as Complex Regional Pain Syndrome type one (CRPS 1).2,3,4 It is also prescribed to multiple sclerosis patients to control dysesthesias and may be useful in reducing neuropathic pain caused by cancer and HIV infection. It does not bind to GABA receptors, does not influence neural uptake of GABA, and does not inhibit the GABA-metabolizing enzyme, GABA transaminase.5,6 Unlike GABA, which does not pass through the blood-brain barrier, gabapentin penetrates into the central nervous system and binds to the α2δ-type voltage-gated calcium channels. The mechanism for the analgesic and anticonvulsant effects of gabapentin are not known.2,3,4,5,6
1
Malcangio, M., and Bowery, N.G. GABA and its receptors in the spinal cord. Trends Pharmacol Sci17457-462(1996).
2
van de Vusse, A.C., Stonmp-van de Berg, S.G.M., Kessels, A.H.F., et al. Randomised controlled trial of gabapentin in complex regional pain syndrome type I [ISRCTN84121379]. BMC Neurol4(13)(2004).
3
Hahn, K., Arendt, G., Braun, J.S., et al. A placebo-controlled trial of gabapentin for painful HIV-associated sendory neuropathies. J Neurol2511260-1266(2004).
4
Caraceni, A., Zecca, E., Bonezzi, C., et al. Gabapentin for neuropathic cancer pain: A randomized controlled trial from the gabapentin cancer pain study group. J Clin Oncol22(14)2909-2917(2004).
5
Gee, N.S., Brown, J.P., Dissanayake, V.U.K., et al. The novel anticonvulsant drug, gabapentin (neurontin), binds to the α2δ subunit of a calcium channel. J Biol Chem271(10)5768-5776(1996).
6
Goa, K.L., and Sorkin, E.M. Gabapentin. A review of its pharmacological properties and clinical potential in epilepsy. Drugs46(3)409-427(1993).
Synonyms
Neurontin®
Formal Name
1-(aminomethyl)-cyclohexaneacetic acid
CAS Number
60142-96-3
Molecular Formula
C9H17NO2
Formula Weight
171.2
Formulation
A crystalline solid
Purity
≥98%
Stability
2 years
Storage
-20°C
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
NCC1(CCCCC1)CC(=O)O
Background Reading
Malcangio, M., and Bowery, N.G. GABA and its receptors in the spinal cord. Trends Pharmacol Sci17457-462(1996).
Hahn, K., Arendt, G., Braun, J.S., et al. A placebo-controlled trial of gabapentin for painful HIV-associated sendory neuropathies. J Neurol2511260-1266(2004).
Gee, N.S., Brown, J.P., Dissanayake, V.U.K., et al. The novel anticonvulsant drug, gabapentin (neurontin), binds to the α2δ subunit of a calcium channel. J Biol Chem271(10)5768-5776(1996).
Goa, K.L., and Sorkin, E.M. Gabapentin. A review of its pharmacological properties and clinical potential in epilepsy. Drugs46(3)409-427(1993).
Caraceni, A., Zecca, E., Bonezzi, C., et al. Gabapentin for neuropathic cancer pain: A randomized controlled trial from the gabapentin cancer pain study group. J Clin Oncol22(14)2909-2917(2004).
van de Vusse, A.C., Stonmp-van de Berg, S.G.M., Kessels, A.H.F., et al. Randomised controlled trial of gabapentin in complex regional pain syndrome type I [ISRCTN84121379]. BMC Neurol4(13)(2004).