U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C6H11NO2
Molecular Weight 129.157
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VIGABATRIN

SMILES

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

InChI

InChIKey=PJDFLNIOAUIZSL-UHFFFAOYSA-N
InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)

HIDE SMILES / InChI

Molecular Formula C6H11NO2
Molecular Weight 129.157
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Vigabatrin is an anticonvulsant chemically unrelated to other anticonvulsants. Vigabatrin prevents the catabolism of GABA by irreversibly inhibiting the enzyme GABA transaminase. It is an analog of GABA, but it is not a receptor agonist. However, vigabatrin is not a potent inhibitor of GABA-T with a Ki of 10 mM. Vigabatrin increases brain concentrations of gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter in the CNS, by irreversibly inhibiting enzymes that catabolize GABA (gamma-aminobutyric acid transaminase, GABA-T). Duration of action is determined by rate of GABA-T re-synthesis. Vigabatrin may also work by suppressing repetitive neuronal firing through inhibition of voltage-sensitive sodium channels. Although administered as a racemic mixture, only the S(+) enantiomer is pharmacologically active. Vigabatrin is sold under the trade name SABRIL, it is indicated as adjunctive therapy for adults and pediatric patients 10 years of age and older with refractory complex partial seizures who have inadequately responded to several alternative treatments and for whom the potential benefits outweigh the risk of vision loss.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.85 mM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SABRIL

Cmax

ValueDoseCo-administeredAnalytePopulation
18.4 μg/mL
2 g single, oral
VIGABATRIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
73 μg × h/mL
2 g single, oral
VIGABATRIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
2 g single, oral
VIGABATRIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
2 g single, oral
VIGABATRIN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Refractory Complex Partial Seizures Adults >16 years of age: Initiate therapy at 500 mg twice daily, increasing total daily dose per instructions. The recommended dose is 1500 mg twice daily (2.2). Pediatrics 10 to 16 years of age: Treatment is based on body weight. Initiate therapy at 250 mg twice daily, increasing total daily dose per instructions. The recommended maintenance dose is 1000 mg twice daily. Patients weighing more than 60 kg should be dosed according to adult recommendations (2.2). Infantile Spasms Initiate therapy at 50 mg/kg/day given in 2 divided doses increasing total daily dose per instructions to a maximum of 150 mg/kg/day given in 2 divided doses (2.3). Given orally with or without food.
Route of Administration: Oral
In Vitro Use Guide
Vigabatrin inhibits the uptake of taurine in Caco-2 and MDCK cells to 34 ± 3 and 53 ± 2%, respectively, at a concentration of 30 mM.
Substance Class Chemical
Record UNII
GR120KRT6K
Record Status Validated (UNII)
Record Version