| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-10-17 02:37:49 -0600 |
| Update Date |
2013-02-08 17:13:46 -0700 |
| 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  ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- Neurontin
- 1-(Aminomethyl)cyclohexaneacetic acid
- Aclonium
- Gabapentin
- Gabapentine
- Gabapentino
- Gabapentinum
- Gabapetin
- 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 |
|
| 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) |
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| Predicted Properties |
|
| Spectra |
|---|
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|
| Biological Properties |
|---|
| Cellular Locations |
Not Available
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| Biofluid Locations |
|
| Tissue Location |
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.31 +/- 0.012 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank 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 |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Gabapentin |
| NuGOwiki Link |
HMDB05015 |
| Metagene Link |
HMDB05015 |
| METLIN ID |
2989 |
| PubChem Compound |
3446 |
| PDB ID |
GBN |
| 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 |
- Nemeroff CB: The role of GABA in the pathophysiology and treatment of anxiety disorders. Psychopharmacol Bull. 2003;37(4):133-46.
Pubmed: 15131523
- 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
- 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
- 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
- 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
- Czapinski P, Blaszczyk B, Czuczwar SJ: Mechanisms of action of antiepileptic drugs. Curr Top Med Chem. 2005;5(1):3-14.
Pubmed: 15638774
|
