gamma-Amino-beta-hydroxybutyric acid

Source: Wikipedia, the free encyclopedia.
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
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

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

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

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. ^
    ISBN 978-3-88763-075-1
    .
  2. ^
    ISBN 978-1-4665-7789-3
    .
  3. ISBN 978-0-19-514007-1
    .
  4. S2CID 71239193
    .
  5. ^
    PMID 13642322
    .
  6. ^
    ISBN 978-3-319-46044-4
    .
  7. PMID 6267220
    .
  8. S2CID 1436623
    .
  9. PMID 7466221
    .
  10. PMID 9711762
    .
  11. PMID 11830761
    .
  12. ISBN 978-3-7692-2114-5
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Gamma-Amino-beta-hydroxybutyric_acid&oldid=1188421401"