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γ-Amino-β-hydroxybutyric acid (GABOB) (brand names Gamibetal, Gabomade, Aminoxan, Bogil, Diastal, Gabimex, Gaboril, Kolpo) is an anticonvulsant which is used for the treatment of epilepsy in Europe, Japan, and Mexico.^[1]^[2] It is also an endogenous active metabolite and analogue of the neurotransmitter γ-aminobutyric acid (GABA), and for this reason, may function as a neurotransmitter itself.^[2]^[3]^[4]^[5] 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]^[6] 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.^[7]^[8] GABOB has two stereoisomers, with the (3S) isomer d-GABOB being around twice as potent an anticonvulsant as the (3R) isomer l-GABOB.^[9]

References

^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 44–. ISBN 978-3-88763-075-1.
^ ^a ^b Michael Bryant Smith (23 October 2013). Methods of Non-α-Amino Acid Synthesis, Second Edition. CRC Press. pp. 146–. ISBN 978-1-4665-7789-3.
^ Jack R. Cooper; Floyd E. Bloom; Robert H. Roth (2003). The Biochemical Basis of Neuropharmacology. Oxford University Press. pp. 112–. ISBN 978-0-19-514007-1.
^ Melis, Gian B.; Paoletti, A. M.; Mais, V.; Mastrapasqua, N. M.; Strigini, F.; Fruzzetti, F.; Guarnieri, G.; Gambacciani, M.; Fioretti, P. (2014). "Dose-related effects of γ-amino β-hydroxy butyric acid (GABOB) infusion on growth hormone secretion in normal women". Journal of Endocrinological Investigation 5 (2): 101–106. doi:10.1007/BF03350499. ISSN 0391-4097.
^ ^a ^b Hayashi, Takashi (1959). "The inhibitory action of β-hydroxy-γ-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. ISSN 0022-3751.
^ De Maio, D.; Pasquariello, G. (1963). "Gamma-amino-beta-hydroxybutyric acid (GABOB) and brain serotonin". Psychopharmacologia 5 (1): 84–86. doi:10.1007/BF00405577. ISSN 0033-3158.
^ 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). "γ-Amino-β-hydroxybutyric acid as add-on therapy in adult patients with severe focal epilepsy". Stereotactic and Functional Neurosurgery 69 (1–4 Pt 2): 243–236. doi:10.1159/000099882. PMID 9711762.
^ Roberts E, Krause DN, Wong E, Mori A (1981). "Different Efficacies of d- and l-γ-Amino-β-Hydroxybutyric Acids in GABA Receptor and Transport Test Systems" (PDF). Journal of Neuroscience 1 (2): 132–140. PMID 6267220.

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English Journal

Differentiating enantioselective actions of GABOB: a possible role for threonine 244 in the binding site of GABA(C) ρ(1) receptors.

Yamamoto I1, Absalom N, Carland JE, Doddareddy MR, Gavande N, Johnston GA, Hanrahan JR, Chebib M.
ACS chemical neuroscience.ACS Chem Neurosci.2012 Sep 19;3(9):665-73. Epub 2012 Apr 26.
Designing potent and subtype-selective ligands with therapeutic value requires knowledge about how endogenous ligands interact with their binding site. 4-Amino-3-hydroxybutanoic acid (GABOB) is an endogenous ligand found in the central nervous system in mammals. It is a metabolic product of GABA, th
PMID 23019493

An efficient transformation of cyclic ene-carbamates into omega-(N-formylamino)carboxylic acids by ruthenium tetroxide oxidation.

Kaname M1, Yoshifuji S, Sashida H.
Chemical & pharmaceutical bulletin.Chem Pharm Bull (Tokyo).2008 Sep;56(9):1310-3.
The ruthenium tetroxide (RuO(4)) oxidation of cyclic ene-carbamates resulted in the endo-cyclic carbon-carbon double bond cleavage to afford the corresponding omega-(N-formylamino)carboxylic acids in good yields. Substituted cyclic ene-carbamates derived from (3R)-3-hydroxypiperidine hydrochloride w
PMID 18758107

Enantioselective actions of 4-amino-3-hydroxybutanoic acid and (3-amino-2-hydroxypropyl)methylphosphinic acid at recombinant GABA(C) receptors.

Hinton T1, Chebib M, Johnston GA.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2008 Jan 1;18(1):402-4. Epub 2007 Oct 17.
The R- and S-enantiomers of 4-amino-3-hydroxybutanoic acid (GABOB) were full agonists at human recombinant rho1 GABA(C) receptors. Their enantioselectivity (R>S) matched that reported for their agonist actions at GABA(B) receptors, but was the opposite to that reported at GABA(A) receptors (S>
PMID 17981464

Japanese Journal

Oxidative C–C bond cleavage of N-alkoxycarbonylated cyclic amines by sodium nitrite in trifluoroacetic acid

Onomura Osamu,Moriyama Atsushi,Fukae Kazuhiro,Yamamoto Yutaka,Maki Toshihide,Matsumura Yoshihiro,Demizu Yosuke
Tetrahedron Letters 49(47), 6728-6731, 2008-11-17
… Optically active 3-hydroxypiperidine derivatives and 3-pipecolinate were converted to enantiomerically pure (R)-4-amino-3-hydroxybutanoic acid (GABOB) and (S)-2-pyrrolidone-4-carboxylate, respectively. …
NAID 120000912070

ラット膀胱機能に対する塩酸プロピベリンと GABOB (γ-amino-β-hydroxybutyric acid) の併用効果

小島圭二,鳴尾精一,滝川浩,香川征,長尾光啓
西日本泌尿器科 58(7), 722-725, 1996-07-20
NAID 10019080834

塩酸テロジリン, GABOB併用療法が有効であった切迫性尿失禁の1例 : 第48回四国地方会

梶本昌昭,滝川浩,西谷真明,CHOWDHURY M.G.,香川征
日本泌尿器科學會雜誌 83(2), 258, 1992-02-20
NAID 110003086299

Related Pictures

140418-GaboB CLASIFICACIÓN DE ANSIOLÍTICOS/SEDANTES Gallery of Gabob Keyword Images

★リンクテーブル★

リンク元	「γ-アミノ-β-ヒドロキシ酪酸」
関連記事	「GAB」

「γ-アミノ-β-ヒドロキシ酪酸」

*gamma*-Amino-*beta*-hydroxybutyric acid
Systematic (IUPAC) name
	4-amino-3-hydroxybutanoic acid
Identifiers
CAS Registry Number	352-21-6
PubChem	CID: 2149
ChemSpider	2064
Chemical data
Formula	C4H9NO3
Molecular mass	119.12 g/mol