ContaminantDB: Vigabatrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:19 UTC

Update Date

2026-03-26 18:48:14 UTC

Accession Number

CHEM002339

Identification

Common Name

Vigabatrin

Class

Small Molecule

Description

Vigabatrin is only found in individuals that have used or taken this drug. It is an analogue of gamma-aminobutyric acid. It is an irreversible inhibitor of 4-aminobutyrate transaminase, the enzyme responsible for the catabolism of gamma-aminobutyric acid. (From Martindale The Extra Pharmacopoeia, 31st ed)It is believed that 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) or block the reuptake of GABA into glia and nerve endings. Vigabatrin may also work by suppressing repetitive neuronal firing through inhibition of voltage-sensitive sodium channels.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anticonvulsant
Drug
Enzyme Inhibitor
GABA Agent
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Amino-5-hexenoic acid	ChEBI
gamma-Vinyl gaba	ChEBI
gamma-Vinyl-gamma-aminobutyric acid	ChEBI
GVG	ChEBI
Vigabatrina	ChEBI
Vigabatrine	ChEBI
Vigabatrinum	ChEBI
Sabril	Kegg
4-Amino-5-hexenoate	Generator
g-Vinyl gaba	Generator
Γ-vinyl gaba	Generator
g-Vinyl-g-aminobutyrate	Generator
g-Vinyl-g-aminobutyric acid	Generator
gamma-Vinyl-gamma-aminobutyrate	Generator
Γ-vinyl-γ-aminobutyrate	Generator
Γ-vinyl-γ-aminobutyric acid	Generator
Acid, gamma-vinyl-gamma-aminobutyric	HMDB
Yamanouchi brand OF vigabatrin	HMDB
gamma Vinyl gaba	HMDB
gamma-Vinyl-gaba	HMDB
Sabrilex	HMDB
Vigabatrin aventis brand	HMDB
Hoechst brand OF vigabatrin	HMDB
Vigabatrin hoechst brand	HMDB
gamma Vinyl gamma aminobutyric acid	HMDB
Aventis brand OF vigabatrin	HMDB
Vigabatrin yamanouchi brand	HMDB

Chemical Formula

C₆H₁₁NO₂

Average Molecular Mass

129.157 g/mol

Monoisotopic Mass

129.079 g/mol

CAS Registry Number

60643-86-9

IUPAC Name

4-aminohex-5-enoic acid

Traditional Name

vigabatrin

SMILES

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

InChI Identifier

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

InChI Key

PJDFLNIOAUIZSL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Medium-chain fatty acid
Amino fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

gamma-amino acid (CHEBI:63638 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

anticonvulsant

Biological Roles

EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor

Chemical Roles

EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	55.1 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	96.6 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.1	ChemAxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	4.61	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.29 m³·mol⁻¹	ChemAxon
Polarizability	13.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-ed9483c326234125f4ad	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-004i-3900000000-6c317e49ab8cc532a558	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-9400000000-0215823a9ba364cc48cb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-9400000000-c7d21d36dfb8e7079ee2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-9200000000-e0c504f980ef5bbc0501	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-9000000000-e1b2ea8d5a2da84a5a64	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-9000000000-52958176067fd9bae916	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-9000000000-263da4b132ca66986967	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01b9-9000000000-1f8826cc32ef269c1a7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9000000000-32306e2f90cd529accc7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0gb9-9000000000-aefa9f2682087c7b78ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00di-9000000000-2e8122bd9fa086c48c81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00di-9000000000-c89fa23e4a66cb1fda0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00di-9000000000-ee55e365ddd88597a424	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 120V, Positive	splash10-01b9-9000000000-59ee75afd49600cf9595	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 150V, Positive	splash10-014i-9000000000-32306e2f90cd529accc7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00di-9200000000-6c0ed7a9357b20c8ddec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-9400000000-67f3710d9b1a8968c528	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 180V, Positive	splash10-0gb9-9000000000-aefa9f2682087c7b78ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-3900000000-5bf6d0079fa19a719d28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-9400000000-1d89cce66d591018b8b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9000000000-25ce972a542597293a60	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-14e6a479b3001860431b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-7900000000-fd7f3b3f074734314a87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9100000000-db0d4ab6ed018a7e6a3f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9400000000-6179584a37d7e78d7234	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9000000000-ff84f320ba47dd80531b	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Rapidly absorbed following oral administration, absorption is comparable between neonates, infants, and children. Cmax, 50 mg/kg dose, neonates= 14 mg/L; Tmax, 50 mg/kg dose, neonates = 2.1 hours; However, extent of absorption is higher and elimination half life is longer in neonates compared to children and infants. This is because neonates have reduced renal function compared to the aforementioned population groups. AUC, 50 mg/kg dose, neonates = 142.6 ± 44.0 mg/L/hr; Food may slightly decrease the rate (Cmax decreased by 33%, Tmax increased to 2 hours), but not the extent of absorption. Furthermore, vigabatrin does not cross the blood-brain-barrier well, thus high doses are needed.

Mechanism of Toxicity

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.

Metabolism

Almost no metabolic transformation. Does not induce the hepatic cytochrome P450 system. Route of Elimination: Eliminated primarily through renal excretion as unchanged drugs (80%). Half Life: Neonates, 50 mg/kg = 7.5 ± 2.1 hours (due to reduced renal function); Infants = 5.7 hours; Adults = 7.5 hours; Elderly = 12 - 13 hours

Toxicity Values

LD50, oral, rat: 3000 mg/kg

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For use as an adjunct in treatment resistant epilepsy, refractory complex partial seizures, and secondary generalized seizures. It is also used as monotherapy in infantile spasms in West syndrome.

Minimum Risk Level

Not Available

Health Effects

May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID