Vigabatrin

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 Search

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

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.drugbank.ca/drugs/DB01080
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Gamma-amino-N-butyrate transaminase 9 Target ID: CHEMBL2044 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020427s000lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/22061176	Inhibitor 8504		0.85 mM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 121 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020427s000lbl.pdf	Primary		Approved 8583	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 2009

C_max

Value	Dose	Co-administered	Analyte	Population
18.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8331204/	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

Value	Dose	Co-administered	Analyte	Population
73 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8331204/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8331204/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020427s021,022006s023lbl.pdf	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/1483856	unhealthy, 16-63 Health Status: unhealthy Age Group: 16-63 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1483856	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: https://pubmed.ncbi.nlm.nih.gov/1483856
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: https://pubmed.ncbi.nlm.nih.gov/8331204	healthy, 25.8 ± 8.2 Health Status: healthy Age Group: 25.8 ± 8.2 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/8331204	Sources: https://pubmed.ncbi.nlm.nih.gov/8331204
4 g single, oral Highest studied dose Dose: 4 g Route: oral Route: single Dose: 4 g Sources: https://pubmed.ncbi.nlm.nih.gov/8331204	healthy, 27.0 ± 8.2 Health Status: healthy Age Group: 27.0 ± 8.2 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/8331204	Sources: https://pubmed.ncbi.nlm.nih.gov/8331204
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: https://pubmed.ncbi.nlm.nih.gov/9924905	unhealthy, 35 ± 11 Health Status: unhealthy Age Group: 35 ± 11 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9924905	Sources: https://pubmed.ncbi.nlm.nih.gov/9924905
90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020427s010s011s012,022006s011s012s013lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020427s010s011s012,022006s011s012s013lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020427s010s011s012,022006s011s012s013lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020427s010s011s012,022006s011s012s013lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020427s010s011s012,022006s011s012s013lbl.pdf	Other AEs: Vision loss, Brain MRI signal changes... Other AEs: Vision loss Brain MRI signal changes Suicidal behavior Suicidal ideation Anemia Somnolence Fatigue Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020427s010s011s012,022006s011s012s013lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087	inducer 440		inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A 227		CYP2B6 669 CYP2C19 329 CYP3A 142

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0	likely	weak (co-administration study) Comment: A 16% to 20% average reduction in total phenytoin plasma levels was reported (see label page 21) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0	likely	weak (co-administration study) Comment: A 16% to 20% average reduction in total phenytoin plasma levels was reported (see label page 21) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0
CYP3A 317	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020427s000lbl.pdf#page=22 Page: 22.0	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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020427s000lbl.pdf#page=22 Page: 22.0
CYP3A 317	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020427s000lbl.pdf#page=22 Page: 22.0	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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020427s000lbl.pdf#page=22 Page: 22.0
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0	not significant
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0	not significant

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022006s000_ClinPharm.pdf#page=4 Page: 4.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63638	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63638
ChemicalBook	CB1285620	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1285620
eMolecules	595429	https://www.emolecules.com/cgi-bin/more?vid=595429
MolPort	MolPort-003-666-796	https://www.molport.com/shop/molecule-link/MolPort-003-666-796

PubMed

Title	Date	PubMed
Visual field defect associated with vigabatrin: observational cohort study.	1999 Oct 30	10541505
Vigabatrin-associated visual field defects in children.	2000 Jun	11026995
Visual field defects in patients taking vigabatrin.	2000 Oct	11037919
Behavioural effects of the new anticonvulsants.	2001	11444724
Effects of antiepileptic drugs on cognition.	2001	11422358
Visual function is stable in patients who continue long-term vigabatrin therapy: implications for clinical decision making.	2001 Apr	11440348
GABA transaminase inhibition induces spontaneous and enhances depolarization-evoked GABA efflux via reversal of the GABA transporter.	2001 Apr 15	11306616
Paradoxical reduction of synaptic inhibition by vigabatrin.	2001 Aug	11495935
The effect of gamma-vinyl-GABA on the consumption of concurrently available oral cocaine and ethanol in the rat.	2001 Feb	11267634
Adverse event monitoring in lamotrigine patients: a pharmacoepidemiologic study in the United Kingdom.	2001 Feb	11240596
Multifocal ERG and full-field ERG in patients on long-term vigabatrin medication.	2001 Jan	11475366
Nicotine-conditioned locomotor activity in rats: dopaminergic and GABAergic influences on conditioned expression.	2001 Jan	11274718
Influence of pyridoxal 5'-phosphate alone and in combination with vigabatrin on brain GABA measured by 1H-NMR-spectroscopy.	2001 Jul 1	11543957
Chronic elevation of brain GABA levels beginning two days after status epilepticus does not prevent epileptogenesis in rats.	2001 Mar	11249963
Development of a stable-isotope dilution assay for gamma-aminobutyric acid (GABA) transaminase in isolated leukocytes and evidence that GABA and beta-alanine transaminases are identical.	2001 Mar	11238307
[Vigabatrin-induced cytolytic hepatitis].	2001 May	11521114
[Therapeutic strategy in severe encephalopathies].	2001 May 1-15	11424039
West syndrome and other infantile epileptic encephalopathies--Indian hospital experience.	2001 Nov	11701262
Gamma vinyl-GABA differentially modulates NMDA antagonist-induced increases in mesocortical versus mesolimbic DA transmission.	2001 Nov	11682254
Vigabatrin protects against hippocampal damage but is not antiepileptogenic in the lithium-pilocarpine model of temporal lobe epilepsy.	2001 Nov	11673025
Decrease in GABA synthesis rate in rat cortex following GABA-transaminase inhibition correlates with the decrease in GAD(67) protein.	2001 Sep 28	11578600
Determination of vigabatrin in human plasma and urine by high-performance liquid chromatography with fluorescence detection.	2001 Sep 5	11530978
Spectrofluorimetric determination of vigabatrin and gabapentin in urine and dosage forms through derivatization with fluorescamine.	2002 Jan 1	11682233

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 Created by `admin` on `Mon Mar 31 18:38:39 GMT 2025` Edited by `admin` on `Mon Mar 31 18:38:39 GMT 2025`
Record UNII	GR120KRT6K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Vigabatrin

Official Name

English

SABRIL

Preferred Name

English

Vigabatrin [WHO-DD]

Common 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-

Systematic Name

English

MDL 71,754

Code

English

RMI-71754

Code

English

CPP-109

Code

English

GAMMA VINYL GABA

Common Name

English

VIGABATRIN [USP-RS]

Common Name

English

MDL-71754

Code

English

VIGAFYDE

Brand Name

English

Vigabatrin [VANDF]

Common Name

English

Vigabatrin [MI]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

609817