Anticonvulsant drug
Pharmaceutical compound
γ-Amino-β-hydroxybutyric acid (GABOB ), also known asβ-hydroxy-γ-aminobutyric acid (β-hydroxy-GABA ), sold under the brand nameGamibetal among others, is ananticonvulsant which is used for the treatment ofepilepsy inEurope ,Japan , andMexico .[ 1] [ 2] GABA analogue , or ananalogue of theneurotransmitter γ-aminobutyric acid (GABA), and has been found to be anendogenous metabolite of GABA.[ 2] [ 3] [ 4] [ 5]
GABOB is an anticonvulsant and is used in the treatment ofepilepsy .[ 1] [ 2]
GABOB is aGABA receptor agonist .[ 6] stereoisomers , and showsstereoselectivity in its actions.[ 6] R )-(–)-GABOB is a moderate-potency agonist of theGABAB receptor , while (S )-(+)-GABOB is apartial agonist of the GABAB receptor and an agonist of theGABAA receptor .[ 6] S )-(+)-GABOB is around twice as potent an anticonvulsant as (R )-(–)-GABOB.[ 7] racemic mixture .[ 6]
Relative to GABA, GABOB has more potentinhibitory effects on thecentral nervous system , perhaps due to its greater capacity to cross theblood–brain barrier .[ 5] [ 8] adjuvant treatment used alongside another anticonvulsant.[ 9] [ 10]
GABOB, or β-hydroxy-GABA, is a closestructural analogue of GABA (seeGABA analogue ), as well as ofγ-hydroxybutyric acid (GHB),phenibut (β-phenyl-GABA),baclofen (β-(4-chlorophenyl)-GABA),[ 11] pregabalin (β-isobutyl-GABA).
Society and culture [ edit ] GABOB has been referred to by thegeneric name buxamine orbuxamina .[ 1] [ 6]
GABOB is sold primarily under the brand name Gamibetal.[ 1] [ 1] [ 12]
^a b c d e Index Nominum 2000: International Drug Directory ISBN 978-3-88763-075-1 ^a b c 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 ^ Cooper JR, Bloom FE, Roth RH (2003).The Biochemical Basis of Neuropharmacology 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 b 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 .PMC 1356963 PMID 13642322 . ^a b c d e Corelli F, Mugnaini C (17 January 2017)."Chemistry of GABAB Receptor 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 .PMC 6564147 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 .PMC 6494145 PMID 11830761 . ^ Muller NF (19 June 1998).European Drug Index: European Drug Registrations ISBN 978-3-7692-2114-5
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor Positive modulators (abridged; seehere for a full list): α-EMTBL Alcohols (e.g.,drinking alcohol ,2M2B )Anabolic steroids Avermectins (e.g.,ivermectin )Barbiturates (e.g.,phenobarbital )Benzodiazepines (e.g.,diazepam )Bromide compounds (e.g.,potassium bromide )Carbamates (e.g.,meprobamate )Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g.,ergoloid (dihydroergotoxine) )Etazepine Etifoxine Fenamates (e.g.,mefenamic acid )Flavonoids (e.g.,apigenin ,hispidulin )Fluoxetine Flupirtine Imidazoles (e.g.,etomidate )Kava constituents (e.g.,kavain )Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g.,allopregnanolone ,cholesterol ,THDOC )Niacin Niacinamide Nonbenzodiazepines (e.g.,β-carbolines (e.g.,abecarnil ),cyclopyrrolones (e.g.,zopiclone ),imidazopyridines (e.g.,zolpidem ),pyrazolopyrimidines (e.g.,zaleplon ))Norfluoxetine Petrichloral Phenols (e.g.,propofol )Phenytoin Piperidinediones (e.g.,glutethimide )Propanidid Pyrazolopyridines (e.g.,etazolate )Quinazolinones (e.g.,methaqualone )Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g.,baicalin )Stiripentol Sulfonylalkanes (e.g.,sulfonmethane (sulfonal) )Topiramate Valerian constituents (e.g.,valerenic acid )Volatiles /gases (e.g.,chloral hydrate ,chloroform ,diethyl ether ,paraldehyde ,sevoflurane )Negative modulators: 1,3M1B 3M2B 11-Ketoprogesterone 17-Phenylandrostenol α3IA α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Anabolic steroids Amiloride Anisatin β-Lactams (e.g.,penicillins ,cephalosporins ,carbapenems )Basmisanil Bemegride Bicyclic phosphates (TBPS ,TBPO ,IPTBO )BIDN Bilobalide Bupropion CHEB Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g.,fipronil )Flavonoids (e.g.,amentoflavone ,oroxylin A )Flumazenil Fluoroquinolones (e.g.,ciprofloxacin )Flurothyl Furosemide Golexanolone Iomazenil (123 I) IPTBO Isopregnanolone (sepranolone) L-655,708 Laudanosine Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Nonsteroidal antiandrogens (e.g.,apalutamide ,bicalutamide ,enzalutamide ,flutamide ,nilutamide )Oenanthotoxin Pentylenetetrazol (pentetrazol) Phenylsilatrane Picrotoxin (i.e.,picrotin ,picrotoxinin anddihydropicrotoxinin )Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426 GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
