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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H11NO2
Molecular Weight 129.157
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VIGABATRIN, (R)-

SMILES

N[C@H](CCC(O)=O)C=C

InChI

InChIKey=PJDFLNIOAUIZSL-YFKPBYRVSA-N
InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1

HIDE SMILES / InChI

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

Description

VIGABATRIN, R-(-)- is an inactive enantiomer of gamma-vinyl-gamma-aminobutyric acid. Vigabatrin exists as a 50/50 racemic mixture of two enantiomers. It is an irreversible inhibitor of the GABA-transaminase, the enzyme responsible for the catabolism of GABA, thus increasing the GABAergic transmission. This drug is mainly prescribed for the treatment of West syndrome, a deleterious pediatric epileptic syndrome also known as infantile spasms. The maximum and minimum plasma concentrations of vigabatrin at steady-state were lower for the S(+) than for the R(-) enantiomer, while the apparent oral clearance was higher for the S(+) than for the R(-) enantiomer in a patient affected with tuberous sclerosis who developed major agitation and aggression and in whom impaired renal function was diagnosed. The question remains of the potential toxicity of the high levels of the R(-) enantiomer. The placental uptake of the active S(+)-isomer from the maternal circulation exceeded that of the R(-)-isomer and this was reflected by a corresponding difference in placental tissue concentrations.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Rat: 150 mg/kg
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
ODN92S847A
Record Status Validated (UNII)
Record Version