Human Metabolome Database Version 3.5

Showing metabocard for Gabapentin (HMDB05015)

Record Information
Version 3.5
Creation Date 2006-10-17 02:37:49 -0600
Update Date 2013-05-29 13:41:30 -0600
HMDB ID HMDB05015
Secondary Accession Numbers None
Metabolite Identification
Common 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Neurontin
  2. 1-(Aminomethyl)cyclohexaneacetic acid
  3. Aclonium
  4. Gabapentin
  5. Gabapentine
  6. Gabapentino
  7. Gabapentinum
  8. Gabapetin
  9. Novo-Gabapentine
Chemical Formula C9H17NO2
Average Molecular Weight 171.2368
Monoisotopic Molecular Weight 171.125928793
IUPAC Name 2-[1-(aminomethyl)cyclohexyl]acetic acid
Traditional IUPAC Name gabapentin
CAS Registry Number 60142-96-3
SMILES NCC1(CC(O)=O)CCCCC1
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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Gamma Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
Substituents
  • Carboxylic Acid
  • Cyclohexane
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Gamma Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Drug
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 165 - 167 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -1.10 SANGSTER (1994)
Predicted Properties
Property Value Source
Water Solubility 4.34 g/L ALOGPS
LogP -1.88 ALOGPS
LogP -1.3 ChemAxon
LogS -1.60 ALOGPS
pKa (strongest acidic) 4.63 ChemAxon
pKa (strongest basic) 9.91 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 63.32 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 46.33 ChemAxon
Polarizability 18.88 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location
  • Brain
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.31 +/- 0.012 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023587
KNApSAcK ID Not Available
Chemspider ID 3328 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Gabapentin Link_out
NuGOwiki Link HMDB05015 Link_out
Metagene Link HMDB05015 Link_out
METLIN ID 2989 Link_out
PubChem Compound 3446 Link_out
PDB ID GBN Link_out
ChEBI ID Not Available
References
Synthesis Reference Satzinger, Gerhard; Hartenstein, Johannes; Herrmann, Manfred; Heldt, Wolfgang. Cyclic amino acids. Ger. Offen. (1976), 16 pp. CODEN: GWXXBX DE 2460891 19760701 CAN 85:94679 AN 1976:494679
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Nemeroff CB: The role of GABA in the pathophysiology and treatment of anxiety disorders. Psychopharmacol Bull. 2003;37(4):133-46. Pubmed: 15131523 Link_out
  2. Di Trapani G, Mei D, Marra C, Mazza S, Capuano A: Gabapentin in the prophylaxis of migraine: a double-blind randomized placebo-controlled study. Clin Ter. 2000 May-Jun;151(3):145-8. Pubmed: 10958046 Link_out
  3. Bisaga A, Aharonovich E, Garawi F, Levin FR, Rubin E, Raby WN, Nunes EV: A randomized placebo-controlled trial of gabapentin for cocaine dependence. Drug Alcohol Depend. 2006 Feb 28;81(3):267-74. Epub 2005 Oct 5. Pubmed: 16169160 Link_out
  4. Petroff OA, Rothman DL, Behar KL, Lamoureux D, Mattson RH: The effect of gabapentin on brain gamma-aminobutyric acid in patients with epilepsy. Ann Neurol. 1996 Jan;39(1):95-9. Pubmed: 8572673 Link_out
  5. Taylor CP, Gee NS, Su TZ, Kocsis JD, Welty DF, Brown JP, Dooley DJ, Boden P, Singh L: A summary of mechanistic hypotheses of gabapentin pharmacology. Epilepsy Res. 1998 Feb;29(3):233-49. Pubmed: 9551785 Link_out
  6. Czapinski P, Blaszczyk B, Czuczwar SJ: Mechanisms of action of antiepileptic drugs. Curr Top Med Chem. 2005;5(1):3-14. Pubmed: 15638774 Link_out
  7. Cheng JK, Chiou LC: Mechanisms of the antinociceptive action of gabapentin. J Pharmacol Sci. 2006;100(5):471-86. Epub 2006 Feb 11. Pubmed: 16474201 Link_out

Enzymes
Name: Branched-chain-amino-acid aminotransferase, cytosolic
Reactions: Not Available
Gene Name: BCAT1
Uniprot ID: P54687 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenosine receptor A1
Reactions: Not Available
Gene Name: ADORA1
Uniprot ID: P30542 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Voltage-dependent calcium channel subunit alpha-2/delta-1
Reactions: Not Available
Gene Name: CACNA2D1
Uniprot ID: P54289 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Voltage-dependent calcium channel subunit alpha-2/delta-2
Reactions: Not Available
Gene Name: CACNA2D2
Uniprot ID: Q9NY47 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Voltage-dependent N-type calcium channel subunit alpha-1B
Reactions: Not Available
Gene Name: CACNA1B
Uniprot ID: Q00975 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA