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Substance Name: Vigabatrin [USAN:INN:BAN]
RN: 68506-86-5
UNII: GR120KRT6K
InChIKey: PJDFLNIOAUIZSL-UHFFFAOYSA-N

Notes

  • 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)
  • 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)

Molecular Formula

  • C6-H11-N-O2

Molecular Weight

  • 129.1579
 

Classification Codes

  • Anticonvulsants
  • Central Nervous System Agents
  • Enzyme Inhibitors
  • GABA Agents
  • Neurotransmitter Agents

Names and Synonyms

Name of Substance

  • Vigabatrin
  • Vigabatrin [USAN:INN:BAN]

MeSH Heading

  • Vigabatrin

Synonyms

  • (+-)-gamma-Vinyl GABA
  • 4-Amino-5-hexenoic acid
  • CPP 109
  • CPP109
  • EINECS 270-929-6
  • gamma-Vinyl GABA
  • gamma-Vinyl-GABA
  • GVG
  • MDL 71754
  • RMI 71754
  • Sabril
  • UNII-GR120KRT6K
  • Vigabatrin
  • Vigabatrina [Spanish]
  • Vigabatrine
  • Vigabatrine [French]
  • Vigabatrinum
  • Vigabatrinum [Latin]

Systematic Names

  • (1)-4-Aminohex-5-enoic acid
  • 5-Hexenoic acid, 4-amino-

Registry Numbers

CAS Registry Number

  • 68506-86-5

FDA UNII

  • GR120KRT6K

Other Registry Number

  • 60643-86-9

System Generated Number

  • 0068506865

Structure Descriptors

InChI

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

InChIKey

PJDFLNIOAUIZSL-UHFFFAOYSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 55mg/kg/2Y-I (55mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE Lancet. Vol. 354, Pg. 486, 1999.
man TDLo unreported 57mg/kg/2D-I (57mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BRAIN AND COVERINGS: CHANGES IN SURFACE EEG
Lancet. Vol. 342, Pg. 619, 1993.
mouse LD50 intraperitoneal > 2500mg/kg (2500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Neuropharmacology. Vol. 21, Pg. 803, 1982.
mouse LD50 oral 3gm/kg (3000mg/kg)   Toxicologic Pathology. Vol. 18, Pg. 225, 1990.
rat LD50 oral 3gm/kg (3000mg/kg)   Toxicologic Pathology. Vol. 18, Pg. 225, 1990.
women TDLo unreported 80mg/kg/4D-I (80mg/kg) BRAIN AND COVERINGS: CHANGES IN SURFACE EEG

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Lancet. Vol. 342, Pg. 185, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -2.16E+00 (none)   EXP
Water Solubility 5.51E+04 mg/L 25 EST
Vapor Pressure 6.95E-09 mm Hg 25 EST
Henry's Law Constant 1.30E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.23E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.