Contents

gamma-Amino-beta-hydroxybutyric acid

Anticonvulsant drug

γ-Amino-β-hydroxybutyric acid

Clinical data
Trade names	Gamibetal, others
Other names	Buxamine; Buxamina; Bussamina; γ-Amino-β-hydroxybutyric acid; GABOB; β-Hydroxy-γ-aminobutyric acid; β-Hydroxy-GABA
Identifiers
IUPAC name (±)-4-amino-3-hydroxybutanoic acid
CAS Number	924-49-2 352-21-6
PubChem CID	2149
ChemSpider	2064
UNII	1ZHM019FLD
KEGG	D00174
ChEBI	CHEBI:16080
ChEMBL	ChEMBL93515
CompTox Dashboard (EPA)	DTXSID1045877
ECHA InfoCard	100.011.916
Chemical and physical data
Formula	C4H9NO3
Molar mass	119.120 g·mol−1
3D model (JSmol)	Interactive image
SMILES C(C(CN)O)C(=O)O
InChI 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 epilepsyinEurope, 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[edit]

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

Pharmacology[edit]

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 GABA_B receptor, while (S)-(+)-GABOB is a partial agonist of the GABA_B receptor and an agonist of the GABA_A 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[edit]

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[edit]

Generic name[edit]

GABOB has been referred to by the generic name buxamineorbuxamina.^[1][6]

Brand names[edit]

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[edit]