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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL89598
CHEMBL89598
Compound Name VIGABATRIN
ChEMBL Synonyms MDL 71,754 | SABRIL | GAMMA-VINYL GABA | VIGABATRIN | VINYL GAMMA-AMINOBUTYRIC ACID
Max Phase 4 (Approved)
Trade Names SABRIL
Molecular Formula C6H11NO2

Additional synonyms for CHEMBL89598 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NC(CCC(=O)O)C=C
Standard InChI InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)
Standard InChI Key PJDFLNIOAUIZSL-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL89598

Molecule Features

CHEMBL89598 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Gamma-amino-N-butyrate transaminase inhibitor Gamma-amino-N-butyrate transaminase FDA PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Spasms, InfantileD013036Orphanet:3451West syndrome4ClinicalTrials
DailyMed
DailyMed
Tourette SyndromeD005879EFO:0004895Tourette syndrome1ClinicalTrials
Tuberous SclerosisD014402Orphanet:805Tuberous sclerosis2ClinicalTrials
AlcoholismD000437EFO:0003829alcohol dependence2ClinicalTrials
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence2ClinicalTrials
EpilepsyD004827EFO:0000474epilepsy4ATC
Amphetamine-Related DisordersD019969EFO:0004701metamphetamine dependence2ClinicalTrials
Epilepsy, Complex PartialD017029EFO:1000877complex partial epilepsy4DailyMed
DailyMed

Clinical Data

ClinicalTrials.gov VIGABATRIN
The Cochrane Collaboration VIGABATRIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
129.2 129.079 0.36 4 63.32 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 2 0 3 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.36 10.61 -.3 -2.8 0 9 0.54

Structural Alerts

There are 4 structural alerts for CHEMBL89598. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N03 - ANTIEPILEPTICS
N03A - ANTIEPILEPTICS
N03AG - Fatty acid derivatives
N03AG04 - vigabatrin

ChemSpider ChemSpider:PJDFLNIOAUIZSL-UHFFFAOYSA-N
DailyMed vigabatrin
PubChem SID: 104171263 SID: 144203852 SID: 26747129 SID: 26751903 SID: 50104581 SID: 50104582 SID: 50104583 SID: 85231284 SID: 90340732
Wikipedia Vigabatrin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL89598



ACToR 74046-07-4 60643-86-9
BindingDB 50118886
Brenda 91636 91632 3140 23509
ChEBI 63638
DrugBank DB01080
DrugCentral 2819
eMolecules 595429
EPA CompTox Dashboard DTXSID4041153
Guide to Pharmacology 4821
Human Metabolome Database HMDB0015212
IBM Patent System DDFE0B832855F2FEFD614DD4F13F04E2
KEGG Ligand C07500
LINCS LSM-4959
MolPort MolPort-003-666-796
Nikkaji J82.341D
PharmGKB PA10231
PubChem 25202592 5665
PubChem: Drugs of the Future 12012774
PubChem: Thomson Pharma 15194489
SureChEMBL SCHEMBL26714

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/PJDFLNIOAUIZSL-UHFFFAOYSA-N spacer
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