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Details

Stereochemistry RACEMIC
Molecular Formula C6H11NO2
Molecular Weight 129.1573
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VIGABATRIN

SMILES

C=CC(CCC(=O)O)N

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

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020427s010s011s012,022006s011s012s013lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22061175

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SABRIL

Approved Use

SABRIL is an antiepileptic drug (AED) indicated for: • Refractory Complex Partial Seizures in Adults (1.1). It should be used as adjunctive therapy in patients who have responded inadequately to several alternative treatments.

Launch Date

1250726400000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
18.4 μg/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
VIGABATRIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
73 μg × h/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
VIGABATRIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
VIGABATRIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
VIGABATRIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Disc. AE: Sedation, Seizures...
Other AEs: Weight gain, Depression...
AEs leading to
discontinuation/dose reduction:
Sedation (9%)
Seizures (2%)
Status epilepticus (1%)
Other AEs:
Weight gain (6%)
Depression (1%)
Excitability (1%)
Itching (1%)
Headache (1%)
Irritability (1%)
Muscle pain (1%)
Libido decreased (1%)
Sources:
2 g 2 times / day multiple, oral
Highest studied dose
Dose: 2 g, 2 times / day
Route: oral
Route: multiple
Dose: 2 g, 2 times / day
Sources:
healthy, 25.8 ± 8.2
Health Status: healthy
Age Group: 25.8 ± 8.2
Sex: M
Sources:
4 g single, oral
Highest studied dose
Dose: 4 g
Route: oral
Route: single
Dose: 4 g
Sources:
healthy, 27.0 ± 8.2
Health Status: healthy
Age Group: 27.0 ± 8.2
Sex: M
Sources:
3 g 2 times / day multiple, oral
Highest studied dose
Dose: 3 g, 2 times / day
Route: oral
Route: multiple
Dose: 3 g, 2 times / day
Sources:
unhealthy, 35 ± 11
Health Status: unhealthy
Age Group: 35 ± 11
Sex: M+F
Sources:
90 g single, oral
Overdose
unhealthy
Other AEs: Coma, Unconsciousness...
Other AEs:
Coma (common)
Unconsciousness (common)
Drowsiness (common)
Vertigo (uncommon)
Psychosis (uncommon)
Apnea (uncommon)
Respiratory depression (uncommon)
Bradycardia (uncommon)
Agitation (uncommon)
Irritability (uncommon)
Confusion (uncommon)
Headache (uncommon)
Hypotension (uncommon)
Abnormal behavior (uncommon)
Seizures (uncommon)
Status epilepticus (uncommon)
Speech disorder (uncommon)
Sources:
1500 mg 2 times / day multiple, oral
Recommended
Dose: 1500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1500 mg, 2 times / day
Sources:
unhealthy
Other AEs: Vision loss, Brain MRI signal changes...
Other AEs:
Vision loss
Brain MRI signal changes
Suicidal behavior
Suicidal ideation
Anemia
Somnolence
Fatigue
Sources:
AEs

AEs

AESignificanceDosePopulation
Depression 1%
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Excitability 1%
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Headache 1%
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Irritability 1%
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Itching 1%
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Libido decreased 1%
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Muscle pain 1%
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Status epilepticus 1%
Disc. AE
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Seizures 2%
Disc. AE
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Weight gain 6%
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Sedation 9%
Disc. AE
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 16-63
Health Status: unhealthy
Age Group: 16-63
Sex: M+F
Sources:
Coma common
90 g single, oral
Overdose
unhealthy
Drowsiness common
90 g single, oral
Overdose
unhealthy
Unconsciousness common
90 g single, oral
Overdose
unhealthy
Abnormal behavior uncommon
90 g single, oral
Overdose
unhealthy
Agitation uncommon
90 g single, oral
Overdose
unhealthy
Apnea uncommon
90 g single, oral
Overdose
unhealthy
Bradycardia uncommon
90 g single, oral
Overdose
unhealthy
Confusion uncommon
90 g single, oral
Overdose
unhealthy
Headache uncommon
90 g single, oral
Overdose
unhealthy
Hypotension uncommon
90 g single, oral
Overdose
unhealthy
Irritability uncommon
90 g single, oral
Overdose
unhealthy
Psychosis uncommon
90 g single, oral
Overdose
unhealthy
Respiratory depression uncommon
90 g single, oral
Overdose
unhealthy
Seizures uncommon
90 g single, oral
Overdose
unhealthy
Speech disorder uncommon
90 g single, oral
Overdose
unhealthy
Status epilepticus uncommon
90 g single, oral
Overdose
unhealthy
Vertigo uncommon
90 g single, oral
Overdose
unhealthy
Anemia
1500 mg 2 times / day multiple, oral
Recommended
Dose: 1500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1500 mg, 2 times / day
Sources:
unhealthy
Brain MRI signal changes
1500 mg 2 times / day multiple, oral
Recommended
Dose: 1500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1500 mg, 2 times / day
Sources:
unhealthy
Fatigue
1500 mg 2 times / day multiple, oral
Recommended
Dose: 1500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1500 mg, 2 times / day
Sources:
unhealthy
Somnolence
1500 mg 2 times / day multiple, oral
Recommended
Dose: 1500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1500 mg, 2 times / day
Sources:
unhealthy
Suicidal behavior
1500 mg 2 times / day multiple, oral
Recommended
Dose: 1500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1500 mg, 2 times / day
Sources:
unhealthy
Suicidal ideation
1500 mg 2 times / day multiple, oral
Recommended
Dose: 1500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1500 mg, 2 times / day
Sources:
unhealthy
Vision loss
1500 mg 2 times / day multiple, oral
Recommended
Dose: 1500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1500 mg, 2 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
weak (co-administration study)
Comment: A 16% to 20% average reduction in total phenytoin plasma levels was reported (see label page 21)
Page: 70
likely
weak (co-administration study)
Comment: A 16% to 20% average reduction in total phenytoin plasma levels was reported (see label page 21)
Page: 70
no
no (co-administration study)
Comment: No significant difference in pharmacokinetic parameters of vigabatrin were found after treatment with ethinyl estradiol and levonorgestrel; vigabatrin did not interfere significantly with the cytochrome P450 isoenzyme (CYP3A)-mediated metabolism of the contraceptive tested
Page: 22
no
no (co-administration study)
Comment: No significant difference in pharmacokinetic parameters of vigabatrin were found after treatment with ethinyl estradiol and levonorgestrel; vigabatrin did not interfere significantly with the cytochrome P450 isoenzyme (CYP3A)-mediated metabolism of the contraceptive tested
Page: 22
not significant
not significant
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
GABA changes with vigabatrin in the developing human brain.
1999 Apr
Characteristics of a unique visual field defect attributed to vigabatrin.
1999 Dec
Visual dysfunction in patients receiving vigabatrin: clinical and electrophysiologic findings.
1999 Dec 10
Elimination of oxcarbazepine-induced oculogyric crisis following vagus nerve stimulation.
1999 Jun 10
Visual field defect associated with vigabatrin: observational cohort study.
1999 Oct 30
[Visual field changes secondary to vigabatrin treatment].
2000 Dec 16-31
Synergistic neurotoxicity by human immunodeficiency virus proteins Tat and gp120: protection by memantine.
2000 Feb
Another case of reversibility of visual-field defect induced by vigabatrin monotherapy: is young age a favorable factor?
2000 Jun
Vigabatrin-associated visual field defects in children.
2000 Jun
Effect of long-term vigabatrin administration on the immature rat brain.
2000 Jun
A controlled study of vigabatrin and visual abnormalities.
2000 May
Visual field defect associated with vigabatrin. Many more patients may be affected than were found in study.
2000 May 20
Electro-oculography, electroretinography, visual evoked potentials, and multifocal electroretinography in patients with vigabatrin-attributed visual field constriction.
2000 Nov
[Acute encephalopathy and myoclonic status induced by vigabatrin monotherapy] .
2000 Oct
Visual field defects in patients taking vigabatrin.
2000 Oct
Human brain GABA transaminase tissue distribution and molecular expression.
2000 Sep
Anti-spasticity agents for multiple sclerosis.
2001
Visual field defects and other ophthalmological disturbances associated with vigabatrin.
2001
The value of electrophysiology results in patients with epilepsy and vigabatrin associated visual field loss.
2001 Apr
[Antiepileptic drugs and neuropathic pain].
2001 Feb 16-28
The role of vigabatrin in childhood seizure disorders: results from a clinical audit.
2001 Jan
Effects of vigabatrin on brain GABA+/CR signals in patients with epilepsy monitored by 1H-NMR-spectroscopy: responder characteristics.
2001 Jan
The wide field multifocal ERG reveals a retinal defect caused by vigabatrin toxicity.
2001 Jan
Progress report on new antiepileptic drugs: a summary of the Fifth Eilat Conference (EILAT V).
2001 Jan
Revised guideline for prescribing vigabatrin in children. Guideline's claim about infantile spasms is not based on appropriate evidence.
2001 Jan 27
[Vigabatrin and visual fields defects].
2001 Jan 8
Gabapentin but not vigabatrin is effective in the treatment of acquired nystagmus in multiple sclerosis: How valid is the GABAergic hypothesis?
2001 Jul
[Reversible phenytoin-induced extrapontine myelinolysis].
2001 Jun
Gamma-vinyl GABA reduces paired pulse inhibition in the rat dentate gyrus in vivo and in vitro.
2001 May
[Therapeutic strategy in severe encephalopathies].
2001 May 1-15
What is West syndrome?
2001 Nov
Gamma vinyl-GABA differentially modulates NMDA antagonist-induced increases in mesocortical versus mesolimbic DA transmission.
2001 Nov
Vigabatrin decreases cholecystokinin-tetrapeptide (CCK-4) induced panic in healthy volunteers.
2001 Nov
Vigabatrin protects against hippocampal damage but is not antiepileptogenic in the lithium-pilocarpine model of temporal lobe epilepsy.
2001 Nov
Pharmacologic rescue of lethal seizures in mice deficient in succinate semialdehyde dehydrogenase.
2001 Oct
Decrease in GABA synthesis rate in rat cortex following GABA-transaminase inhibition correlates with the decrease in GAD(67) protein.
2001 Sep 28
Patents

Patents

Sample Use Guides

Refractory Complex Partial Seizures
Route of Administration: Oral
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.
Name Type Language
VIGABATRIN
DASH   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
4-AMINO-5-HEXENOIC ACID
Systematic Name English
GAMMA-VINYL GABA
Common Name English
VIGABATRIN [INN]
Common Name English
VIGABATRIN [USP MONOGRAPH]
Common Name English
VINYL GAMMA-AMINOBUTYRIC ACID
Systematic Name English
VIGABATRIN [USAN]
Common Name English
VIGABATRIN [ORANGE BOOK]
Common Name English
VIGABATRIN, (+/-)-
Common Name English
VIGABATRIN [MART.]
Common Name English
VIGABATRIN [EP MONOGRAPH]
Common Name English
VIGABATRIN [JAN]
Common Name English
5-HEXENOIC ACID, 4-AMINO-
Common Name English
MDL 71,754
Code English
RMI-71754
Code English
SABRIL
Brand Name English
VIGABATRIN [WHO-DD]
Common Name English
CPP-109
Code English
GAMMA VINYL GABA
Common Name English
VIGABATRIN [USP-RS]
Common Name English
MDL-71754
Code English
VIGABATRIN [VANDF]
Common Name English
VIGABATRIN [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 609817
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
NCI_THESAURUS C264
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
FDA ORPHAN DRUG 135100
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
WHO-ATC N03AG04
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
LIVERTOX 1027
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
NDF-RT N0000175753
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
WHO-VATC QN03AG04
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
Code System Code Type Description
PUBCHEM
5665
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
RXCUI
14851
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB01080
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
MESH
D020888
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
LACTMED
Vigabatrin
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
WIKIPEDIA
VIGABATRIN
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
FDA UNII
GR120KRT6K
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
NCI_THESAURUS
C87611
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
EVMPD
SUB00048MIG
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
CAS
60643-86-9
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
SUPERSEDED
INN
5581
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
IUPHAR
4821
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
DRUG CENTRAL
2819
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
MERCK INDEX
M11445
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY Merck Index
CAS
68506-86-5
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
ChEMBL
CHEMBL89598
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY
USP_CATALOG
1712001
Created by admin on Fri Jun 25 20:33:20 UTC 2021 , Edited by admin on Fri Jun 25 20:33:20 UTC 2021
PRIMARY USP-RS