FComEx: Gabapentin (PC000864)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:08 UTC

Update date

2017-01-19 02:36:39 UTC

FoodComEx ID

PC000864

FoodDB Record

FDB023587

Chemical Information

Name

Gabapentin

Description

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]

CAS Number

60142-96-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-(Aminomethyl)cyclohexaneacetate	Generator
1-(Aminomethyl)cyclohexaneacetic acid	hmdb
Aclonium	hmdb
Gabapentin	hmdb
Gabapentina	ChEBI
Gabapentine	hmdb
Gabapentino	hmdb
Gabapentinum	hmdb
Gabapetin	hmdb
Neurontin	hmdb
Novo-Gabapentine	hmdb

Chemical Formula

C9H17NO2

IUPAC name

2-[1-(aminomethyl)cyclohexyl]acetic acid

InChI Identifier

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

Isomeric SMILES

NCC1(CC(O)=O)CCCCC1

Average Molecular Weight

171.2368

Monoisotopic Molecular Weight

171.125928793

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents