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 Anticonvulsants (also known as antiepileptic drugs or recently as antiseizure drugs) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of b ...

which is used for the treatment of epilepsy in Europe,

Japan Japan ( ja, 日本, or , and formally , ''Nihonkoku'') is an island country in East Asia. It is situated in the northwest Pacific Ocean, and is bordered on the west by the Sea of Japan, while extending from the Sea of Okhotsk in the north ...

, and Mexico. It is a GABA analogue, or an analogue of the

neurotransmitter A neurotransmitter is a signaling molecule secreted by a neuron to affect another cell across a synapse. The cell receiving the signal, any main body part or target cell, may be another neuron, but could also be a gland or muscle cell. Neuro ...

γ-aminobutyric acid (GABA), and has been found to be an

endogenous Endogenous substances and processes are those that originate from within a living system such as an organism, tissue, or cell. In contrast, exogenous substances and processes are those that originate from outside of an organism. For example, es ...

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

of GABA.

Medical uses

GABOB is an anticonvulsant and is used in the treatment of epilepsy.

Pharmacology

GABOB is a

GABA receptor agonist A GABA receptor agonist is a drug that is an agonist for one or more of the GABA receptors, producing typically sedative effects, and may also cause other effects such as anxiolytic, anticonvulsant, and muscle relaxant effects. There are three rece ...

. It has two stereoisomers, and shows stereoselectivity in its actions. Specifically, (''R'')-(–)-GABOB is a moderate-

potency Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of how ...

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

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. (''S'')-(+)-GABOB is around twice as potent an anticonvulsant as (''R'')-(–)-GABOB. GABOB is used medically as a

racemic mixture In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...

. 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 The blood–brain barrier (BBB) is a highly selective semipermeable membrane, semipermeable border of endothelium, endothelial cells that prevents solutes in the circulating blood from ''non-selectively'' crossing into the extracellular fluid of ...

. However, GABOB is of relatively low potency as an anticonvulsant when used by itself, and is more useful as an

adjuvant In pharmacology, an adjuvant is a drug or other substance, or a combination of substances, that is used to increase the efficacy or potency of certain drugs. Specifically, the term can refer to: * Adjuvant therapy in cancer management * Analgesic ...

treatment used alongside another anticonvulsant.

Chemistry

GABOB, or β-hydroxy-GABA, is a close structural analogue of GABA (see GABA analogue), as well as of γ-hydroxybutyric acid (GHB),

phenibut Phenibut, sold under the brand names Anvifen, Fenibut, and Noofen among others, is a central nervous system depressant with anxiolytic effects, and is used to treat anxiety, insomnia, and for a variety of other indications. It is usually taken ...

(β-phenyl-GABA), baclofen (β-(4-chlorophenyl)-GABA), and pregabalin (β-isobutyl-GABA).

Society and culture

Generic name

GABOB has been referred to by the generic name ''buxamine'' or ''buxamina''.

Brand names

GABOB is sold primarily under the brand name Gamibetal. It has also been marketed under a variety of other brand names including Aminoxan, Bogil, Diastal, Gabimex, Gabomade, Gaboril, Gamalate, and Kolpo.

References

{{DEFAULTSORT:Amino-beta-hydroxybutyric acid, gamma- Amino acids Anticonvulsants Beta hydroxy acids GABA analogues GABAA receptor agonists GABAB receptor agonists Human metabolites Neurotransmitters