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
Spectrofluorimetric determination of vigabatrin and gabapentin in urine and dosage forms through derivatization with fluorescamine.	2002-01-01	11682233
West syndrome and other infantile epileptic encephalopathies--Indian hospital experience.	2001-11	11701262
West syndrome: a university hospital based study from Oman.	2001-11	11701261
National survey of West syndrome in Taiwan.	2001-11	11701257
National survey on West syndrome in Korea.	2001-11	11701256
Infantile spasms in tuberous sclerosis complex.	2001-11	11701245
What is West syndrome?	2001-11	11701238
Gamma vinyl-GABA differentially modulates NMDA antagonist-induced increases in mesocortical versus mesolimbic DA transmission.	2001-11	11682254
Vigabatrin decreases cholecystokinin-tetrapeptide (CCK-4) induced panic in healthy volunteers.	2001-11	11682253
Vigabatrin protects against hippocampal damage but is not antiepileptogenic in the lithium-pilocarpine model of temporal lobe epilepsy.	2001-11	11673025
Randomized trial of vigabatrin in patients with infantile spasms.	2001-10-23	11673582
[Social and economic aspects of administration of new antiepileptic drugs].	2001-10-16	11599223
Single systemic dose of vigabatrin induces early proconvulsant and later anticonvulsant effect in rats.	2001-10-12	11578840
Infantile spasms: diagnosis and assessment of treatment response by video-EEG.	2001-10	11665822
Anxiolytic effects of vigabatrin in panic disorder.	2001-10	11593085
Pharmacologic rescue of lethal seizures in mice deficient in succinate semialdehyde dehydrogenase.	2001-10	11544478
Decrease in GABA synthesis rate in rat cortex following GABA-transaminase inhibition correlates with the decrease in GAD(67) protein.	2001-09-28	11578600
Determination of vigabatrin in human plasma and urine by high-performance liquid chromatography with fluorescence detection.	2001-09-05	11530978
Plasticity of rat central inhibitory synapses through GABA metabolism.	2001-09-01	11533137
Gamma-vinyl GABA (GVG) blocks expression of the conditioned place preference response to heroin in rats.	2001-09-01	11391783
Concentric visual field restriction under vigabatrin therapy: extent depends on the duration of drug intake.	2001-09	11700995
Effects of radiofrequency exposure on the GABAergic system in the rat cerebellum: clues from semi-quantitative immunohistochemistry.	2001-08-31	11520491
Spectrofluorimetric determination of vigabatrin and gabapentin in dosage forms and spiked plasma samples through derivatization with 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole.	2001-08-15	11501899
Is hyperprolinemia type I actually a benign trait? Report of a case with severe neurologic involvement and vigabatrin intolerance.	2001-08	11510941
Newer antiepileptic drugs: advantages and disadvantages.	2001-08	11504596
Paradoxical reduction of synaptic inhibition by vigabatrin.	2001-08	11495935
Vigabatrin effect on inner retinal function.	2001-08	11470707
Visual field constriction: accumulation of vigabatrin but not tiagabine in the retina.	2001-07-24	11468302
Influence of pyridoxal 5'-phosphate alone and in combination with vigabatrin on brain GABA measured by 1H-NMR-spectroscopy.	2001-07-01	11543957
Gabapentin but not vigabatrin is effective in the treatment of acquired nystagmus in multiple sclerosis: How valid is the GABAergic hypothesis?	2001-07	11413274
[Therapeutic strategy in severe encephalopathies].	2001-06-26	11424039
[Reversible phenytoin-induced extrapontine myelinolysis].	2001-06	11433706
Visual field loss associated with vigabatrin: pathological correlations.	2001-06	11385015
[Vigabatrin-induced cytolytic hepatitis].	2001-05	11521114
Vigabatrin visual toxicity: evolution and dose dependence.	2001-05	11380567
Visual function is stable in patients who continue long-term vigabatrin therapy: implications for clinical decision making.	2001-04	11440348
[Vigabatrin and visual fields defects].	2001-01-08	11379251
Multifocal ERG and full-field ERG in patients on long-term vigabatrin medication.	2001-01	11475366
Anti-spasticity agents for multiple sclerosis.	2001	11687107
A risk-benefit assessment of treatments for infantile spasms.	2001	11665869
Adverse effects of antiepileptic drugs on bone structure: epidemiology, mechanisms and therapeutic implications.	2001	11524035
The management of refractory idiopathic epilepsies.	2001	11520320
Management strategies for refractory localization-related seizures.	2001	11520319
Epileptic encephalopathy.	2001	11520318
GABAergic mechanisms in epilepsy.	2001	11520315
The new generation of GABA enhancers. Potential in the treatment of epilepsy.	2001	11475940
Visual field defects with vigabatrin: epidemiology and therapeutic implications.	2001	11463129
Behavioural effects of the new anticonvulsants.	2001	11444724
Effects of antiepileptic drugs on cognition.	2001	11422358
Visual field defects and other ophthalmological disturbances associated with vigabatrin.	2001	11419565

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