Gamma-Amino-beta-hydroxybutyric acid explained

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.[1] [2] 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.[3] [4] [5]

Medical uses

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

Pharmacology

GABOB is a GABA receptor agonist.[6] 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.[7] 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.[8] 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.[9] [10]

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),[11] 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.[12]

Notes and References

  1. Book: Index Nominum 2000: International Drug Directory. January 2000. Taylor & Francis. 978-3-88763-075-1. 44–.
  2. Book: Smith MB . Biologically Important Amino Acids . Methods of Non-α-Amino Acid Synthesis . Second . https://books.google.com/books?id=pWxmAQAAQBAJ&pg=PA146 . 23 October 2013. CRC Press. 978-1-4665-7789-3. 146–.
  3. Book: Cooper JR, Bloom FE, Roth RH . The Biochemical Basis of Neuropharmacology. 2003. Oxford University Press. 978-0-19-514007-1. 112–.
  4. Melis GB, Paoletti AM, Mais V, Mastrapasqua NM, Strigini F, Fruzzetti F, Guarnieri G, Gambacciani M, Fioretti P . 6 . 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 . 2014 . 7096918 . 10.1007/BF03350499 . 71239193 .
  5. Hayashi T . 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 . March 1959 . 13642322 . 1356963 . 10.1113/jphysiol.1959.sp006163 .
  6. Book: Corelli F, Mugnaini C . Chemistry of GABAB Receptor Ligands: Focus on Agonists and Antagonists . Colombo G . GABAB Receptor. https://books.google.com/books?id=ONHBDQAAQBAJ&pg=PA25 . 17 January 2017. Springer. 978-3-319-46044-4. 25–.
  7. Roberts E, Krause DN, Wong E, Mori A . 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 . February 1981 . 6267220 . 6564147 . 10.1523/JNEUROSCI.01-02-00132.1981 .
  8. Demaio D, Pasquariello G . Gamma-amino-beta-hydroxybutyric acid (GABOB) and brain serotonin . Psychopharmacologia . 5 . 1 . 84–86 . October 1963 . 14085623 . 10.1007/BF00405577 . 1436623 .
  9. Chemello R, Giaretta D, Pellegrini A, Testa G . [Effect of gamma-amino-beta-hydroxybutyric acid (GABHB) on experimentally-induced epileptic activity] . it . Rivista di Neurologia . 50 . 4 . 253–268 . 1980 . 7466221 . Effect of γ-amino-β-hydroxybutyric acid (GABHB) on experimentally-induced epileptic activity .
  10. García-Flores E, Farías R . 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 . 1997 . 9711762 . 10.1159/000099882 .
  11. Lapin I . Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug . CNS Drug Reviews . 7 . 4 . 471–481 . 2001 . 11830761 . 6494145 . 10.1111/j.1527-3458.2001.tb00211.x .
  12. Book: Muller NF . European Drug Index: European Drug Registrations . Fourth . 19 June 1998. CRC Press. 978-3-7692-2114-5. 181–.

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