V8261

Sigma-Aldrich

(±)-Vigabatrin

Synonym(s):
(±)-γ-Vinyl-GABA, (R,S)-4-Amino-5-hexenoic acid, (±)-4-Aminohexenoic acid
Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
Molecular Weight:
129.16
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

originator

Lundbeck

SMILES string

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

InChI

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

InChI key

PJDFLNIOAUIZSL-UHFFFAOYSA-N

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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Packaging

10, 50 mg in poly bottle

Biochem/physiol Actions

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

Features and Benefits

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 is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. V8261.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Peter Weber et al.
Epilepsy & behavior : E&B, 24(1), 138-140 (2012-04-17)
We report the case of an adolescent girl who suffered from symptomatic refractory focal epilepsy after an arteria cerebri media insult 15 years prior to this report. Five weeks after initiation of an add-on therapy with vigabatrin, she was seizure...
The potential value of a negative finding: an illustrative example.
Kenneth Silverman et al.
JAMA psychiatry, 70(6), 571-572 (2013-04-12)
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...
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)
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...
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