Chemistry:Gamma-Amino-beta-hydroxybutyric acid

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Short description: Anticonvulsant drug


γ-Amino-β-hydroxybutyric acid
GABOB.png
GABOB3d.png
Clinical data
Trade namesGamibetal, others
Other namesBuxamine; Buxamina; Bussamina; γ-Amino-β-hydroxybutyric acid; GABOB; β-Hydroxy-γ-aminobutyric acid; β-Hydroxy-GABA
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC4H9NO3
Molar mass119.120 g·mol−1
3D model (JSmol)

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

Medical uses

GABOB is an anticonvulsant and is used in the treatment of epilepsy.[1][2]

Pharmacology

GABOB is a GABA receptor agonist.[6] It has two stereoisomers, and shows stereoselectivity in its actions.[6] 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.[6] (S)-(+)-GABOB is around twice as potent an anticonvulsant as (R)-(–)-GABOB.[7] GABOB is used medically as a racemic mixture.[6]

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.[5][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.[1][6]

Brand names

GABOB is sold primarily under the brand name Gamibetal.[1] It has also been marketed under a variety of other brand names including Aminoxan, Bogil, Diastal, Gabimex, Gabomade, Gaboril, Gamalate, and Kolpo.[1][12]

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 44–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA44. 
  2. ↑ 2.0 2.1 2.2 "Biologically Important Amino Acids". Methods of Non-α-Amino Acid Synthesis (Second ed.). CRC Press. 23 October 2013. pp. 146–. ISBN 978-1-4665-7789-3. https://books.google.com/books?id=pWxmAQAAQBAJ&pg=PA146. 
  3. ↑ The Biochemical Basis of Neuropharmacology. Oxford University Press. 2003. pp. 112–. ISBN 978-0-19-514007-1. https://books.google.com/books?id=vNaM55VDoF8C&pg=PA112. 
  4. ↑ "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. doi:10.1007/BF03350499. PMID 7096918. 
  5. ↑ 5.0 5.1 "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. doi:10.1113/jphysiol.1959.sp006163. PMID 13642322. 
  6. ↑ 6.0 6.1 6.2 6.3 6.4 "Chemistry of GABAB Receptor Ligands: Focus on Agonists and Antagonists". GABAB Receptor. Springer. 17 January 2017. pp. 25–. ISBN 978-3-319-46044-4. https://books.google.com/books?id=ONHBDQAAQBAJ&pg=PA25. 
  7. ↑ "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. doi:10.1523/JNEUROSCI.01-02-00132.1981. PMID 6267220. 
  8. ↑ "Gamma-amino-beta-hydroxybutyric acid (GABOB) and brain serotonin". Psychopharmacologia 5 (1): 84–86. October 1963. doi:10.1007/BF00405577. PMID 14085623. 
  9. ↑ "[Effect of gamma-amino-beta-hydroxybutyric acid (GABHB) on experimentally-induced epileptic activity]" (in it). Rivista di Neurologia 50 (4): 253–268. 1980. PMID 7466221. 
  10. ↑ "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. doi:10.1159/000099882. PMID 9711762. 
  11. ↑ "Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug". CNS Drug Reviews 7 (4): 471–481. 2001. doi:10.1111/j.1527-3458.2001.tb00211.x. PMID 11830761. 
  12. ↑ European Drug Index: European Drug Registrations (Fourth ed.). CRC Press. 19 June 1998. pp. 181–. ISBN 978-3-7692-2114-5. https://books.google.com/books?id=2HBPHmclMWIC&pg=PA181. 

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See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators

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