V8261

(±)-Vigabatrin

Name: (±)-Vigabatrin
Brand: SIGMA

Synonym(s):

(R,S)-4-Amino-5-hexenoic acid, (±)-γ-Vinyl-GABA, (±)-4-Aminohexenoic acid

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About This Item

Empirical Formula (Hill Notation):

C₆H₁₁NO₂

CAS Number:

68506-86-5

Molecular Weight:

129.16

NACRES:

NA.77

PubChem Substance ID:

24278202

UNSPSC Code:

12352200

EC Number:

270-929-6

MDL number:

MFCD00274577

InChI key

PJDFLNIOAUIZSL-UHFFFAOYSA-N

InChI

1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)

SMILES string

NC(CCC(O)=O)C=C

originator

Lundbeck

Quality Level

200

Gene Information

human ... ABAT(18), GABBR1(2550), GABBR2(9568), GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562)

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Related Categories

Bioactive Small Molecule Inhibitors

Biochem/physiol Actions

Irreversible GABA transaminase inhibitor. Increases intracellular concentration of GABA in nerve endings; possesses antiepileptic activity.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the GABA Transporters, GABAA Receptors and Glutamate/GABA Synthesis and Metabolism pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Lundbeck. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

GHS08

signalword

Danger

hcodes

H372

pcodes

P260 - P264 - P270 - P314 - P501

Hazard Classifications

STOT RE 1

target_organs

Eyes,Central nervous system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Animal models of the epilepsies.

R S Fisher

Brain research. Brain research reviews, 14(3), 245-278 (1989-07-01)

The study of mechanisms of the epilepsies requires employment of animal models. Choice of a model system depends upon several factors, including the question to be studied, the type of epilepsy to be modelled, familiarity and convenience. Over 50 models

Probing the steric requirements of the γ-aminobutyric acid aminotransferase active site with fluorinated analogues of vigabatrin.

Jose I Juncosa et al.

Bioorganic & medicinal chemistry, 21(4), 903-911 (2013-01-12)

We have synthesized three analogues of 4-amino-5-fluorohexanoic acids as potential inactivators of γ-aminobutyric acid aminotransferase (GABA-AT), which were designed to combine the potency of their shorter chain analogue, 4-amino-5-fluoropentanoic acid (AFPA), with the greater enzyme selectivity of the antiepileptic vigabatrin

Taurine is a crucial factor to preserve retinal ganglion cell survival.

Nicolas Froger et al.

Advances in experimental medicine and biology, 775, 69-83 (2013-02-09)

Retinal ganglion cells (RGCs) are spiking neurons, which send visual information to the brain, through the optic nerve. RGC degeneration occurs in retinal diseases, either as a primary process or secondary to photoreceptor loss. Mechanisms involved in this neuronal degeneration

Vigabatrin-related magnetic resonance imaging abnormalities in an infant with tuberous sclerosis complex and infantile spasms.

David T Hsieh et al.

The Journal of pediatrics, 162(1), 215-215 (2012-09-18)

Drosophila expressing mutant human KCNT1 transgenes make an effective tool for targeted drug screening in a whole animal model of KCNT1-epilepsy.

Rashid Hussain et al.

Scientific reports, 14(1), 3357-3357 (2024-02-10)

Mutations in the KCNT1 potassium channel cause severe forms of epilepsy which are poorly controlled with current treatments. In vitro studies have shown that KCNT1-epilepsy mutations are gain of function, significantly increasing K+ current amplitudes. To investigate if Drosophila can

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