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Showing drug card for Vigabatrin (DB01080)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:17
Primary Accession Number DB01080
Secondary Accession Number
  • APRD00282
Name Vigabatrin
Drug Type
  • Approved
  • Small Molecule
Description 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)
Synonyms Not Available
Brand Names
  1. 4-Amino-5-hexenoic acid
  2. 4-Aminohexenoic acid
  3. GVG
  4. Sabril (TN)
  5. Vigabatrin [USAN:BAN:INN]
  6. Vigabatrina [Spanish]
  7. Vigabatrine
  8. Vigabatrine [French]
  9. Vigabatrinum [Latin]
  10. gamma-Vinyl GABA
Brand Mixtures Not Available
Chemical IUPAC Name 4-aminohex-5-enoic acid
Chemical Formula C6H11NO2
Chemical Structure Structure
CAS Registry Number 60643-86-9
InChI Identifier InChI=1/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/f/h8H
InChI Key PJDFLNIOAUIZSL-FZOZFQFYCQ
KEGG Drug D00535 Link Image
KEGG Compound C07500 Link Image
PubChem Compound 5665 Link Image
PubChem Substance 183802 Link Image
ChEBI ID Not Available
PharmGKB ID PA10231 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02068036 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Vigabatrin Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 129.1570
Monoisotopic Molecular Weight 129.0790
State Solid
Melting Point Not Available
Experimental Water Solubility 55.1 mg/mL Source: PhysProp
Predicted Water Solubility 9.66e+01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 0.1 Source: PhysProp
Predicted LogP -2.55 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -0.13 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID 1OHY Link Image
Experimental PDB File Show
Experimental PDB Structure
Isomeric SMILES N[C@@H](CCC(O)=O)C=C
Canonical SMILES NC(CCC(O)=O)C=C
Drug Category
  • Anticonvulsants
  • Enzyme Inhibitors
  • GABA Agents
ATC Codes
AHFS Codes
  • 28:12.92
Indication For use as an adjunctive treatment (with other drugs) in treatment resistant epilepsy, complex partial seizures, secondary generalized seizures, and for monotherapy use in infantile spasms in West syndrome.
Pharmacology Vigabatrin, is an anticonvulsant chemically unrelated to other anticonvulsants. Vigabatrin inhibits the catabolism of GABA. It is an analog of GABA, but it is not a receptor agonist.
Mechanism of Action 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.
Absorption Rapidly absorbed following oral administration. Food may slightly decrease the rate, but not the extent, of absorption.
Toxicity Not Available
Protein Binding Little to none
Biotransformation Almost no metabolic transformation. Does not induce the hepatic cytochrome P450 system.
Half Life 5-8 hours in young adults, 12-13 hours in elderly.
Dosage Forms
Form Route
Powder Oral
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Zwanzger P, Baghai TC, Schuele C, Strohle A, Padberg F, Kathmann N, Schwarz M, Moller HJ, Rupprecht R: Vigabatrin decreases cholecystokinin-tetrapeptide (CCK-4) induced panic in healthy volunteers. Neuropsychopharmacology. 2001 Nov;25(5):699-703. [PubMed Link Image]
  2. Lindberger M, Luhr O, Johannessen SI, Larsson S, Tomson T: Serum concentrations and effects of gabapentin and vigabatrin: observations from a dose titration study. Ther Drug Monit. 2003 Aug;25(4):457-62. [PubMed Link Image]
  3. Gram L, Larsson OM, Johnsen A, Schousboe A: Experimental studies of the influence of vigabatrin on the GABA system. Br J Clin Pharmacol. 1989;27 Suppl 1:13S-17S. [PubMed Link Image]
  4. Browne TR: Pharmacokinetics of antiepileptic drugs. Neurology. 1998 Nov;51(5 Suppl 4):S2-7. [PubMed Link Image]
  5. Drugs.com Link Image
  6. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. 4-aminobutyrate aminotransferase, mitochondrial
Drug Target 1 [top]
Target 1 ID 280
Target 1 Name 4-aminobutyrate aminotransferase, mitochondrial
Target 1 Synonyms
  1. (S)-3-amino-2-methylpropionate transaminase
  2. 4-aminobutyrate aminotransferase, mitochondrial precursor
  3. EC 2.6.1.19
  4. EC 2.6.1.22
  5. GABA aminotransferase
  6. GABA transaminase
  7. GABA-AT
  8. GABA-T
  9. Gamma-amino-N-butyrate transaminase
  10. L-AIBAT
Target 1 Gene Name ABAT
Target 1 Protein Sequence >4-aminobutyrate aminotransferase, mitochondrial precursor 
MASMLLAQRLACSFQHSYRLLVPGSRHISQAAAKVDVEFDYDGPLMKTEVPGPRSQELMK
QLNIIQNAEAVHFFCNYEESRGNYLVDVDGNRMLDLYSQISSVPIGYSHPALLKLIQQPQ
NASMFVNRPALGILPPENFVEKLRQSLLSVAPKGMSQLITMACGSCSNENALKTIFMWYR
SKERGQRGFSQEELETCMINQAPGCPDYSILSFMGAFHGRTMGCLATTHSKAIHKIDIPS
FDWPIAPFPRLKYPLEEFVKENQQEEARCLEEVEDLIVKYRKKKKTVAGIIVEPIQSEGG
DNHASDDFFRKLRDIARKHGCAFLVDEVQTGGGCTGKFWAHEHWGLDDPADVMTFSKKMM
TGGFFHKEEFRPNAPYRIFNTWLGDPSKNLLLAEVINIIKREDLLNNAAHAGKALLTGLL
DLQARYPQFISRVRGRGTFCSFDTPDDSIRNKLILIARNKGVVLGGCGDKSIRFRPTLVF
RDHHAHLFLNIFSDILADFK
Target 1 Number of Residues 508
Target 1 Molecular Weight 56440
Target 1 Theoretical pI 8.04
Target 1 GO Classification
Function
4-aminobutyrate transaminase activity
binding
vitamin binding
pyridoxal phosphate binding
catalytic activity
transferase activity
transferase activity, transferring nitrogenous groups
transaminase activity
Process
physiological process
metabolism
cellular metabolism
amino acid and derivative metabolism
amino acid derivative metabolism
gamma-aminobutyric acid metabolism
Component
Not Available
Target 1 General Function Amino acid transport and metabolism
Target 1 Specific Function Catalyzes the conversion of gamma-aminobutyrate and L- beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine
Target 1 Pathways
Name SMPDB Link KEGG Link
Valine, leucine and isoleucine degradation SMP00032 Link Image map00280 Link Image
Target 1 Reactions
  • 4-aminobutanoate + 2-oxoglutarate = succinate semialdehyde + L-glutamate
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 602705 Link Image
Target 1 UniProtKB/Swiss-Prot ID P80404 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name GABT_HUMAN Link Image
Target 1 PDB ID 1OHY Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Mitochondrion
  • mitochondrial matrix
Target 1 Gene Sequence >1503 bp 
ATGGCCTCCATGTTGCTCGCCCAGCGGCTGGCCTGCAGCTTCCAGCACACGTACCGCCTG
CTGGTGCCTGGATCCAGACACATTAGTCAAGCTGCAGCCAAAGTCGACGTTGAATTTGAT
TATGATGGGCCTCTGATGAAGACGGAAGTCCCAGGGCCTAGATCTCAGGAGTTAATGAAA
CAGCTGAATATAATTCAGAATGCAGAGGCTGTGCATTTTTTCTGCAATTACGAAGAGAGC
CGAGGCAATTACCTGGTTGATGTGGACGGCAACCGAATGCTGGATCTTTATTCCCAGATC
TCCTCTGTTCCCATAGGTTACAGCGACCCGGCCCTCGTGAAACTCATCCAACAGCCACAA
AATGCGAGCATGTTTGTCAACAGACCCGCCCTCGAAATCCTGCCTCCGGAGAACTTTGTG
GAGAAGCTCCGGCAGTCCTTGCTCTCGGTGGCTCCCAAAGGGATGTCCCAGCTCATCACC
ATGGCCTGCGGCTCCTGCTCCAATGAAAACGCCTTAAAGACCATCTTCATGTGGTACCGG
AGCAAGGAAAGAGGGCAGAGGGGATTCTCCAAAGAGGAGCTGGAGACGTGCATGATTAAC
CAGGCCCCCTGGTGCCCCGACTACAGCATCCTCTCCTTCATGGGTTCCTTCCATGGGAGG
ACCATGGGTTGCTTAGCGACCACGCACTCTAAAGCCATTCACAAGATCGATATCCCTTCC
TTTGACTGGCCCATCGCACCGTTCCCACGGCTGAAATACCCTCTGGAAGAGTTTGTGAAA
GAGAACCAACAGGAAGAGGCCGGCTGTCTGGAAGAGGTTGAGGATCTGATTGTGAAATAT
CGAAAAAAGAAGAAGACGGTGGCCGGGATCATCGTGGAGCCCATCCAGTCCGAGGGTGGA
GACAACCATGCATCCGATGACTTCTTTCGGAAGCTGAGAGACATCGCCAGGAAGCACTGC
TGCGCCTTCTTGGTGGACGAGGTCCAGACCGGAGGAGGCTGCACGGGCAAGTTCTGGGCC
CATGAGCACTGGGGCCTGGATGACCCAGCAGACGTGATGACCTTCAGCAAGAAGATGATG
ACTGGGGGCTTCTTCCTCAAGGAGGAGTTCAGGCCTAATGCTCCCTACCGGATCTTCAAC
ACGTGGCTGGGGGACCCGTCCAAGAACCTGTTGCTGGCTGAGGTCATCAACATCATCAAG
CGGGAGGACCTGCTAAATAATGCAGCCCATGCCGGGAAGGCCCTGCTCACAGGACTGCTG
GACCTCCAGGCCCGGTACCCCCAGTTCATCAGCAGGGTGAGAGGACGAGGCACCTTTTGC
TCCTTCGATACTCCCGATGATTCCATACGGAATAAGCTCATTTTAATTGCCAGAAACAAA
GGTGTGGTGTTGGGTGGCTGTGGTGACAAATCCATTCGTTTCCGTCCCACGCTGGTGTTC
AGGGATCACCACGCTCACCTGTTCCTCAATATTTTCAGTGACATCTTAGCAGACTTCAAG
TAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID ABAT Link Image
Target 1 GenAtlas ID ABAT Link Image
Target 1 HGNC ID HGNC:23 Link Image
Target 1 Chromosome Location 16
Target 1 Locus 16p13.2
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Medina-Kauwe LK, Tobin AJ, De Meirleir L, Jaeken J, Jakobs C, Nyhan WL, Gibson KM: 4-Aminobutyrate aminotransferase (GABA-transaminase) deficiency. J Inherit Metab Dis. 1999 Jun;22(4):414-27. [PubMed Link Image]
  2. Osei YD, Churchich JE: Screening and sequence determination of a cDNA encoding the human brain 4-aminobutyrate aminotransferase. Gene. 1995 Apr 3;155(2):185-7. [PubMed Link Image]
  3. De Biase D, Barra D, Simmaco M, John RA, Bossa F: Primary structure and tissue distribution of human 4-aminobutyrate aminotransferase. Eur J Biochem. 1995 Jan 15;227(1-2):476-80. [PubMed Link Image]
Target 1 Drug References
  1. Weber OM, Verhagen A, Duc CO, Meier D, Leenders KL, Boesiger P: Effects of vigabatrin intake on brain GABA activity as monitored by spectrally edited magnetic resonance spectroscopy and positron emission tomography. Magn Reson Imaging. 1999 Apr;17(3):417-25. [PubMed Link Image]
  2. Valdizan EM, Garcia AP, Armijo JA: Effects of increasing doses of vigabatrin on platelet gamma-aminobutyric acid-transaminase and brain gamma-aminobutyric acid in rats. Eur J Pharmacol. 1999 Mar 19;369(2):169-73. [PubMed Link Image]
  3. Arndt CF, Derambure P, Defoort-Dhellemmes S, Hache JC: Outer retinal dysfunction in patients treated with vigabatrin. Neurology. 1999 Apr 12;52(6):1201-5. [PubMed Link Image]
  4. Molina PE, Ahmed N, Ajmal M, Dewey S, Volkow N, Fowler J, Abumrad N: Co-administration of gamma-vinyl GABA and cocaine: preclinical assessment of safety. Life Sci. 1999;65(11):1175-82. [PubMed Link Image]
  5. French JA: Vigabatrin. Epilepsia. 1999;40 Suppl 5:S11-6. [PubMed Link Image]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]

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