WordNet

to remain unmolested, undisturbed, or uninterrupted -- used only in infinitive form; "let her be"
work in a specific place, with a specific subject, or in a specific function; "He is a herpetologist"; "She is our resident philosopher" (同)follow
have life, be alive; "Our great leader is no more"; "My grandfather lived until the end of war" (同)live
be identical to; be someone or something; "The president of the company is John Smith"; "This is my house"
happen, occur, take place; "I lost my wallet; this was during the visit to my parents house"; "There were two hundred people at his funeral"; "There was a lot of noise in the kitchen"
have the quality of being; (copula, used with an adjective or a predicate noun); "John is rich"; "This is not a good answer"
occupy a certain position or area; be somewhere; "Where is my umbrella?" "The toolshed is in the back"; "What is behind this behavior?"
spend or use time; "I may be an hour"
stake on the outcome of an issue; "I bet $100 on that new horse"; "She played all her money on the dark horse" (同)wager, play
the act of gambling; "he did it on a bet" (同)wager
maintain with or as if with a bet; "I bet she will be there!" (同)wager
street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"
second in order of importance; "the candidate, considered a beta male, was perceived to be unable to lead his party to victory"
the 2nd letter of the Greek alphabet
preliminary or testing stage of a software or hardware product; "a beta version"; "beta software"
a unit of magnetic field strength equal to one-hundred-thousandth of an oersted
the 3rd letter of the Greek alphabet

PrepTutorEJDIC

《連結語として補語を伴なって…『である』,…だ,…です / 《位置・場所を表す語句を伴って》(…に)『ある』,いる(occupy a place or situation) / 〈物事が〉『存在する』,ある(exist);〈生物が〉生存する,生きている(live) / 行われる,起こる,発生する(take place, occur) / 存続する,そのままでいる(remain as before) / 《『be to』 do》 / …する予定である,…することになっている / …すべきだ / 《受動態の不定詞を伴って》…できる / 《命令》…するのだ / 《条件節に》…する意図がある / 《『if…were to』 do》…するとしたなら / 《『be』 do『ing』》《進行形》 / 《進行中の動作》…している,しつつある / 《近い未来》…しようとしている,するつもり / 《動作の反復》(いつも)…している / 《『be』+『他動詞の過去分詞』》《受動態》…される,されている / 《『be』+『自動詞の過去分詞』》《完了形》…した[状態にある]
『かけ』・(…との)かけ《+『with』+『名』》 / かけた物(金) / かけの対象 / 〈金・物〉'を'『かける』 / (かけ事・ゲームなどで)〈人〉‘と'『かけをする』《+『名』〈人〉+『on』+『名』》 / (…に)『かける』《+『on』(『against』)+『名』(one's do『ing』)》
酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
ベータ(ギリシア語アルファベットの第2文字;B,β;英語のB,b に遭当)
ガンマ(ギリシア語アルファベットの第3字Γ,γ;英語のG,gに相当)

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/04/18 05:14:21」(JST)

wiki en

γ-Amino-β-hydroxybutyric acid (GABOB) (brand names Gamibetal, Gabomade, Aminoxan, Bogil, Diastal, Gabimex, Gaboril, Kolpo), or β-hydroxy-γ-aminobutyric acid (β-hydroxy-GABA), 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]

GABOB (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),^[10] and pregabalin (β-isobutyl-GABA).

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.
^ Lapin I (2001). "Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug". CNS Drug Rev 7 (4): 471–81. doi:10.1111/j.1527-3458.2001.tb00211.x. PMID 11830761.

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1. ガンマヒドロキシブチレート（GHB）中毒 gamma hydroxybutyrate ghb intoxication
2. ガンマヒドロキシブチレート（GHB）への依存および離脱 gamma hydroxybutyrate ghb dependence and withdrawal
3. Treatment of narcolepsy in adults
4. Treatment and prognosis of essential tremor
5. Narcolepsy in children

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.Author information 1Faculty of Pharmacy, The University of Sydney, Sydney, NSW 2006, Australia.AbstractDesigning 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, the major inhibitory neurotransmitter. Homology modeling of the GABA(C) ρ(1) receptor revealed a potential H-bond interaction between the hydroxyl group of GABOB and threonine 244 (T244) located on loop C of the ligand binding site of the ρ(1) subunit. Using site-directed mutagenesis, we examined the effect of mutating T244 on the efficacy and pharmacology of GABOB and various ligands. It was found that mutating T244 to amino acids that lacked a hydroxyl group in their side chains produced GABA insensitive receptors. Only by mutating ρ(1)T244 to serine (ρ(1)T244S) produced a GABA responsive receptor, albeit 39-fold less sensitive to GABA than ρ(1)wild-type. We also observed changes in the activities of the GABA(C) receptor partial agonists, muscimol and imidazole-4-acetic acid (I4AA). At the concentrations we tested, the partial agonists antagonized GABA-induced currents at ρ(1)T244S mutant receptors (Muscimol: ρ(1)wild-type, EC(50) = 1.4 μM; ρ(1)T244S, IC(50) = 32.8 μM. I4AA: ρ(1)wild-type, EC(50) = 8.6 μM; ρ(1)T244S, IC(50) = 21.4 μM). This indicates that T244 is predominantly involved in channel gating. R-(-)-GABOB and S-(+)-GABOB are full agonists at ρ(1)wild-type receptors. In contrast, R-(-)-GABOB was a weak partial agonist at ρ(1)T244S (1 mM activates 26% of the current produced by GABA EC(50) versus ρ(1)wild-type, EC(50) = 19 μM; I(max) 100%), and S-(+)-GABOB was a competitive antagonist at ρ(1)T244S receptors (ρ(1)wild-type, EC(50) = 45 μM versus ρ(1)T244S, IC(50) = 417.4 μM, K(B) = 204 μM). This highlights that the interaction of GABOB with T244 is enantioselective. In contrast, the potencies of a range of antagonists tested, 3-aminopropyl(methyl)phosphinic acid (3-APMPA), 3-aminopropylphosphonic acid (3-APA), S- and R-(3-amino-2-hydroxypropyl)methylphosphinic acid (S-(-)-CGP44532 and R-(+)-CGP44533), were not altered. This suggests that T244 is not critical for antagonist binding. Receptor gating is dynamic, and this study highlights the role of loop C in agonist-evoked receptor activation, coupling agonist binding to channel gating.
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.Author information 1Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.AbstractThe 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 were converted into the N-Boc 4-aminobutyric acids by utilization of the RuO(4) oxidation as the key step, which were further transformed into (3R)-4-amino-3-hydroxybutyric acid, an important key intermediate for the synthesis of L-carnitine.
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.Author information 1The Adrien Albert Laboratory of Medicinal Chemistry, Department of Pharmacology, The University of Sydney, NSW 2006, Australia.AbstractThe 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>R). The corresponding methylphosphinic acid analogues proved to be rho1 GABA(C) receptor antagonists with R(+)-CGP44533 being more potent than S(-)-CGP44532, thus showing the opposite enantioselectivity to the agonists R(-)- and S(+)-GABOB. These studies highlight the different stereochemical requirements for the hydroxy group in these analogues at GABA(A), GABA(B) and GABA(C) receptors.
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

Molecular conformations of .GAMMA.-aminobutyric acid and .GAMMA.-amino-.BETA.-hydroxybutyric acid in aqueous solution.

Tanaka Kaori,Akutsu Hideo,Ozaki Yukihiro,Kyogoku Yoshimasa,Tomita Ken-ichi
Bulletin of the Chemical Society of Japan 51(9), 2654-2658, 1978
… Proton magnetic resonance and Raman spectra indicate that the backbone of γ-aminobutyric acid is fairly flexible and rotational isomers are almost equally populated in aqueous solution. … The population is not much affected by change of pH. On the other hand, in γ-amino-β-Hydroxybutyric acid the trans-trans …
NAID 130001969392

Growth hormone release by gamma-aminobutyric acid (GABA) and gamma-amino-.BETA.-hydroxybutyric acid (GABOB) in the rat.

Abe Hiromi [他],KATO YUZURU,CHIHARA KAZUO,OHGO SHOZO,IWASAKI YOSHIKO,IMURA HIROO
Ｅｎｄｏｃｒｉｎｏｌｏｇｉａ　Ｊａｐｏｎｉｃａ 24(2), 229-231, 1977
… Effects of gamma-aminobutyric acid (GABA) and gamma-amino-β-hydroxybutyric acid (GABOB) on growth hormone (GH) release were investigated in the urethaneanesthetized male rat. An intraventricular injection of GABA and L-GABOB but not D-GABOB caused a significant increase in plasma GH. …
NAID 130000955939

インシュリン低血糖状態に関する実験的研究―主として中枢神経系の電気生理学的変化について―

庄盛敏廉
岡山医学会雑誌 74(4-7), 439-461, 1962-07-30
… Arousal effect of excitatory agents and amino acids on insulinhypoglycemia in comparison with that of glucose a) General convulsion Only when general convulsion was induced by electrical stimulation, metrazol and megimide, there could be observed hyperglycemia, awaking patterns on EEG and behavioral wakefulness. … b) Amino acids Sodium glutamate next to glucose had hyperglycemic and arousal action on hypoglycemic cats, but its action was not so fast and long as glucose. …
NAID 120002905913

Related Pictures

★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	「hydroxybutyric acid」「beta」「be」「gamma」

「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 Number	352-21-6
PubChem	CID 2149
ChemSpider	2064
ChEMBL	CHEMBL93515
Chemical data
Formula	C4H9NO3
Molar mass	119.12 g/mol