1.0 2011-09-21 00:32:01 UTC 2015-10-09 22:33:08 UTC FDB023587 Gabapentin Gabapentin was originally developed as a chemical analogue of gamma-aminobutyric acid (GABA) to reduce the spinal reflex for the treatment of spasticity and was found to have anticonvulsant activity in various seizure models. In addition, it also displays antinociceptive activity in various animal pain models. Clinically, gabapentin is indicated as an add-on medication for the treatment of partial seizures, and neuropathic pain. It was also claimed to be beneficial in several other clinical disorders such as anxiety, bipolar disorder, and hot flashes. The possible mechanisms or targets involved in the multiple therapeutic actions of gabapentin have been actively studied. Since gabapentin was developed, several hypotheses had been proposed for its action mechanisms. They include selectively activating the heterodimeric GABA(B) receptors consisting of GABA(B1a) and GABA(B2) subunits, selectively enhancing the NMDA current at GABAergic interneurons, or blocking AMPA-receptor-mediated transmission in the spinal cord, binding to the L-alpha-amino acid transporter, activating ATP-sensitive K(+) channels, activating hyperpolarization-activated cation channels, and modulating Ca(2+) current by selectively binding to the specific binding site of [(3)H]gabapentin, the alpha(2)delta subunit of voltage-dependent Ca(2+) channels. Different mechanisms might be involved in different therapeutic actions of gabapentin. In this review, we summarized the recent progress in the findings proposed for the antinociceptive action mechanisms of gabapentin and suggest that the alpha(2)delta subunit of spinal N-type Ca(2+) channels is very likely the analgesic action target of gabapentin. (PMID: 16474201) [HMDB] 1-(Aminomethyl)cyclohexaneacetate 1-(Aminomethyl)cyclohexaneacetic acid Aclonium Gabapentin Gabapentina Gabapentine Gabapentino Gabapentinum Gabapetin Neurontin Novo-Gabapentine C9H17NO2 171.2368 171.125928793 2-[1-(aminomethyl)cyclohexyl]acetic acid gabapentin 60142-96-3 NCC1(CC(O)=O)CCCCC1 InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12) UGJMXCAKCUNAIE-UHFFFAOYSA-N belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. Gamma amino acids and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic homomonocyclic compounds Amino acids Amino fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic homomonocyclic compound Amine Amino acid Amino fatty acid Carbonyl group Carboxylic acid Fatty acyl Gamma amino acid or derivatives Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine gamma-amino acid Solid logp -1.88 ALOGPS logs -1.60 ALOGPS solubility 4.34e+00 g/l ALOGPS logp -1.3 ChemAxon pka_strongest_acidic 4.63 ChemAxon pka_strongest_basic 9.91 ChemAxon iupac 2-[1-(aminomethyl)cyclohexyl]acetic acid ChemAxon average_mass 171.2368 ChemAxon mono_mass 171.125928793 ChemAxon smiles NCC1(CC(O)=O)CCCCC1 ChemAxon formula C9H17NO2 ChemAxon inchi InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12) ChemAxon inchikey UGJMXCAKCUNAIE-UHFFFAOYSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 46.33 ChemAxon polarizability 18.92 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 2279 Specdb::MsIr 2280 Specdb::MsIr 2281 Specdb::CMs 11411 Specdb::CMs 38835 Specdb::CMs 154506 Specdb::NmrTwoD 1953 Specdb::MsMs 97425 Specdb::MsMs 97426 Specdb::MsMs 97427 Specdb::MsMs 162150 Specdb::MsMs 162151 Specdb::MsMs 162152 Specdb::MsMs 436905 Specdb::MsMs 436906 Specdb::MsMs 436907 Specdb::MsMs 441193 Specdb::MsMs 441194 Specdb::MsMs 441195 Specdb::MsMs 442435 Specdb::MsMs 442436 Specdb::MsMs 442437 Specdb::MsMs 442438 Specdb::MsMs 442439 Specdb::MsMs 442440 Specdb::MsMs 442441 Specdb::MsMs 442442 Specdb::MsMs 442443 Specdb::MsMs 442444 Specdb::MsMs 442445 Specdb::MsMs 442446 Specdb::MsMs 442447 Specdb::NmrOneD 2018 Specdb::NmrOneD 54902 Specdb::NmrOneD 54903 Specdb::NmrOneD 54904 Specdb::NmrOneD 54905 Specdb::NmrOneD 54906 Specdb::NmrOneD 54907 Specdb::NmrOneD 54908 Specdb::NmrOneD 54909 Specdb::NmrOneD 54910 Specdb::NmrOneD 54911 Specdb::NmrOneD 54912 Specdb::NmrOneD 54913 Specdb::NmrOneD 54914 Specdb::NmrOneD 54915 Specdb::NmrOneD 54916 Specdb::NmrOneD 54917 Specdb::NmrOneD 54918 Specdb::NmrOneD 54919 Specdb::NmrOneD 54920 Specdb::NmrOneD 54921 HMDB05015 GBN #<Reference:0x000055ce2f9be8c8> #<Reference:0x000055ce2f968e78> #<Reference:0x000055ce2f9689c8> #<Reference:0x000055ce2f94b8a0> #<Reference:0x000055ce2f931dd8> #<Reference:0x000055ce2f899470> #<Reference:0x000055ce2f79b258> Adenosine receptor A1 P30542 ADORA1 Branched-chain-amino-acid aminotransferase, cytosolic P54687 BCAT1