γ-Amino-β-hydroxybutyric acid

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;
PubChemCID	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	119.120g·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 asβ-hydroxy-γ-aminobutyric acid(β-hydroxy-GABA), sold under the brand nameGamibetalamong others, is ananticonvulsantwhich is used for the treatment ofepilepsyinEurope,Japan,andMexico.^[1]^[2]It is aGABA analogue,or ananalogueof theneurotransmitter γ-aminobutyric acid(GABA), and has been found to be anendogenous metaboliteof GABA.^[2]^[3]^[4]^[5]

Medical uses

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

Pharmacology

GABOB is aGABA receptor agonist.^[6]It has twostereoisomers,and showsstereoselectivityin its actions.^[6]Specifically, (R)-(–)-GABOB is a moderate-potency agonistof theGABA_Breceptor,while (S)-(+)-GABOB is apartial agonistof the GABA_Breceptor and an agonist of theGABA_Areceptor.^[6](S)-(+)-GABOB is around twice as potent an anticonvulsant as (R)-(–)-GABOB.^[7]GABOB is used medically as aracemic mixture.^[6]

Relative to GABA, GABOB has more potentinhibitoryeffects on thecentral nervous system,perhaps due to its greater capacity to cross theblood–brain barrier.^[5]^[8]However, GABOB is of relatively low potency as an anticonvulsant when used by itself, and is more useful as anadjuvanttreatment used alongside another anticonvulsant.^[9]^[10]

Chemistry

GABOB, or β-hydroxy-GABA, is a closestructural analogueof GABA (seeGABA analogue), as well as ofγ-hydroxybutyric acid(GHB),phenibut(β-phenyl-GABA),baclofen(β-(4-chlorophenyl)-GABA),^[11]andpregabalin(β-isobutyl-GABA).

Society and culture

Generic name

GABOB has been referred to by thegeneric namebuxamineorbuxamina.^[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

^^a ^b ^c ^d ^eIndex Nominum 2000: International Drug Directory.Taylor & Francis. January 2000. pp. 44–.ISBN 978-3-88763-075-1.
^^a ^b ^cSmith 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.
^Cooper JR, Bloom FE, Roth RH (2003).The Biochemical Basis of Neuropharmacology.Oxford University Press. pp. 112–.ISBN 978-0-19-514007-1.
^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.
^^a ^bHayashi 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.PMC1356963.PMID 13642322.
^^a ^b ^c ^d ^eCorelli F, Mugnaini C (17 January 2017)."Chemistry of GABA_BReceptor Ligands: Focus on Agonists and Antagonists ".In Colombo G (ed.).GABAB Receptor.Springer. pp. 25–.ISBN 978-3-319-46044-4.
^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.PMC6564147.PMID 6267220.
^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.
^Chemello R, Giaretta D, Pellegrini A, Testa G (1980). "[Effect of gamma-amino-beta-hydroxybutyric acid (GABHB) on experimentally-induced epileptic activity]" [Effect of γ-amino-β-hydroxybutyric acid (GABHB) on experimentally-induced epileptic activity].Rivista di Neurologia(in Italian).50(4):253–268.PMID 7466221.
^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.
^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.PMC6494145.PMID 11830761.
^Muller NF (19 June 1998).European Drug Index: European Drug Registrations(Fourth ed.). CRC Press. pp. 181–.ISBN 978-3-7692-2114-5.

[IndexNominum2000-1] Index Nominum 2000: International Drug Directory.Taylor & Francis. January 2000. pp. 44–.ISBN 978-3-88763-075-1.

[Smith2013-2] 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.

[CooperBloom2003-3] Cooper JR, Bloom FE, Roth RH (2003).The Biochemical Basis of Neuropharmacology.Oxford University Press. pp. 112–.ISBN 978-0-19-514007-1.

[MelisPaoletti2014-4] 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.

[Hayashi1959-5] 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.PMC1356963.PMID 13642322.

[Colombo2017-6] Corelli F, Mugnaini C (17 January 2017)."Chemistry of GABA_BReceptor 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.PMC6564147.PMID 6267220.

[De_MaioPasquariello1963-8] 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 gamma-amino-beta-hydroxybutyric acid (GABHB) on experimentally-induced epileptic activity]" [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.

[pmid11830761-11] 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.PMC6494145.PMID 11830761.

[Muller1998-12] 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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