Gamma-Amino-beta-hydroxybutyric acid

Nowadays, Gamma-Amino-beta-hydroxybutyric acid has become a topic of general interest that covers a wide variety of aspects and its implications have achieved a significant impact on society. From its influence on popular culture to its relevance in the field of science and technology, Gamma-Amino-beta-hydroxybutyric acid has generated constant debate and has sparked the interest of people of all ages and backgrounds. In this article, we will explore different facets of Gamma-Amino-beta-hydroxybutyric acid and analyze its importance in various contexts, providing a comprehensive overview that will allow readers to understand its relevance and possible consequences in today's world.

γ-Amino-β-hydroxybutyric acid
Clinical data
Trade namesGamibetal, others
Other namesBuxamine; Buxamina; Bussamina; γ-Amino-β-hydroxybutyric acid; GABOB; β-Hydroxy-γ-aminobutyric acid; β-Hydroxy-GABA
Identifiers
  • (±)-4-amino-3-hydroxybutanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.011.916 Edit this at Wikidata
Chemical and physical data
FormulaC4H9NO3
Molar mass119.120 g·mol−1
3D model (JSmol)
  • C(C(CN)O)C(=O)O
  • InChI=1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)
  • Key:YQGDEPYYFWUPGO-UHFFFAOYSA-N

γ-Amino-β-hydroxybutyric acid (GABOB), also known as β-hydroxy-γ-aminobutyric acid (β-hydroxy-GABA), and sold under the brand name Gamibetal among others, is an anticonvulsant which is used for the treatment of epilepsy in Europe, Japan, and Mexico. It is a GABA analogue, or an analogue of the neurotransmitter γ-aminobutyric acid (GABA), and has been found to be an endogenous metabolite of GABA.

Medical uses

GABOB is an anticonvulsant and is used in the treatment of epilepsy.

Pharmacology

GABOB is a GABA receptor agonist. It has two stereoisomers, and shows stereoselectivity in its actions. Specifically, (R)-(–)-GABOB is a moderate-potency agonist of the GABAB receptor, while (S)-(+)-GABOB is a partial agonist of the GABAB receptor and an agonist of the GABAA receptor. (S)-(+)-GABOB is around twice as potent an anticonvulsant as (R)-(–)-GABOB. GABOB is used medically as a racemic mixture.

Relative to GABA, GABOB has more potent inhibitory effects on the central nervous system, perhaps due to its greater capacity to cross the blood–brain barrier. However, GABOB is of relatively low potency as an anticonvulsant when used by itself, and is more useful as an adjuvant treatment used alongside another anticonvulsant.

Chemistry

GABOB, or β-hydroxy-GABA, is a close structural analogue of GABA (see GABA analogue), as well as of γ-hydroxybutyric acid (GHB), phenibut (β-phenyl-GABA), baclofen (β-(4-chlorophenyl)-GABA), and pregabalin (β-isobutyl-GABA).

Society and culture

Generic name

GABOB has been referred to by the generic name buxamine or buxamina.

Brand names

GABOB is sold primarily under the brand name Gamibetal. It has also been marketed under a variety of other brand names including Aminoxan, Bogil, Diastal, Gabimex, Gabomade, Gaboril, Gamalate, and Kolpo.

References

  1. ^ a b c d e Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 44–. ISBN 978-3-88763-075-1.
  2. ^ a b c Smith MB (23 October 2013). "Biologically Important Amino Acids". Methods of Non-α-Amino Acid Synthesis (Second ed.). CRC Press. pp. 146–. ISBN 978-1-4665-7789-3.
  3. ^ Cooper JR, Bloom FE, Roth RH (2003). The Biochemical Basis of Neuropharmacology. Oxford University Press. pp. 112–. ISBN 978-0-19-514007-1.
  4. ^ Melis GB, Paoletti AM, Mais V, Mastrapasqua NM, Strigini F, Fruzzetti F, et al. (2014). "Dose-related effects of gamma-amino beta-hydroxy butyric acid (GABOB) infusion on growth hormone secretion in normal women". Journal of Endocrinological Investigation. 5 (2): 101–106. doi:10.1007/BF03350499. PMID 7096918. S2CID 71239193.
  5. ^ a b Hayashi T (March 1959). "The inhibitory action of beta-hydroxy-gamma-aminobutyric acid upon the seizure following stimulation of the motor cortex of the dog". The Journal of Physiology. 145 (3): 570–578. doi:10.1113/jphysiol.1959.sp006163. PMC 1356963. PMID 13642322.
  6. ^ a b c d e Corelli F, Mugnaini C (17 January 2017). "Chemistry of GABAB Receptor Ligands: Focus on Agonists and Antagonists". In Colombo G (ed.). GABAB Receptor. Springer. pp. 25–. ISBN 978-3-319-46044-4.
  7. ^ Roberts E, Krause DN, Wong E, Mori A (February 1981). "Different Efficacies of d- and l-γ-Amino-β-Hydroxybutyric Acids in GABA Receptor and Transport Test Systems". The Journal of Neuroscience. 1 (2): 132–140. doi:10.1523/JNEUROSCI.01-02-00132.1981. PMC 6564147. PMID 6267220.
  8. ^ Demaio D, Pasquariello G (October 1963). "Gamma-amino-beta-hydroxybutyric acid (GABOB) and brain serotonin". Psychopharmacologia. 5 (1): 84–86. doi:10.1007/BF00405577. PMID 14085623. S2CID 1436623.
  9. ^ Chemello R, Giaretta D, Pellegrini A, Testa G (1980). "" [Effect of γ-amino-β-hydroxybutyric acid (GABHB) on experimentally-induced epileptic activity]. Rivista di Neurologia (in Italian). 50 (4): 253–268. PMID 7466221.
  10. ^ García-Flores E, Farías R (1997). "gamma-Amino-beta-hydroxybutyric acid as add-on therapy in adult patients with severe focal epilepsy". Stereotactic and Functional Neurosurgery. 69 (1-4 Pt 2): 243–246. doi:10.1159/000099882. PMID 9711762.
  11. ^ Lapin I (2001). "Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug". CNS Drug Reviews. 7 (4): 471–481. doi:10.1111/j.1527-3458.2001.tb00211.x. PMC 6494145. PMID 11830761.
  12. ^ Muller NF (19 June 1998). European Drug Index: European Drug Registrations (Fourth ed.). CRC Press. pp. 181–. ISBN 978-3-7692-2114-5.
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