vigabatrin   Click here for help

GtoPdb Ligand ID: 4821

Synonyms: CPP-109 | Kigabeq® | MDL-71754 | Sabril® | Vigafyde® (oral solution)
Approved drug
vigabatrin is an approved drug (FDA (2009), EMA (2018))
Compound class: Synthetic organic
Comment: The approved drug vigabatrin is a mixture to two stereoisomers: an R(-)- form (see PubChem CID 157018) and an S(+)-form (see PubChem CID 10219440). Only the S(+)-form is pharmacologically active. The structure shown here does not specify stereochemistry and represents the mixture.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: vigabatrin

vigabatrin is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 63.32
Molecular weight 129.08
XLogP 0.05
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NC(C=C)CCC(=O)O
Isomeric SMILES NC(C=C)CCC(=O)O
InChI 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Abbot EL, Grenade DS, Kennedy DJ, Gatfield KM, Thwaites DT. (2006)
Vigabatrin transport across the human intestinal epithelial (Caco-2) brush-border membrane is via the H+ -coupled amino-acid transporter hPAT1.
Br J Pharmacol, 147 (3): 298-306. [PMID:16331283]
2. Lippert B, Metcalf BW, Jung MJ, Casara P. (1977)
4-amino-hex-5-enoic acid, a selective catalytic inhibitor of 4-aminobutyric-acid aminotransferase in mammalian brain.
Eur J Biochem, 74 (3): 441-5. [PMID:856582]
3. McIntire SL, Reimer RJ, Schuske K, Edwards RH, Jorgensen EM. (1997)
Identification and characterization of the vesicular GABA transporter.
Nature, 389 (6653): 870-6. [PMID:9349821]
4. Silverman RB. (2012)
The 2011 E. B. Hershberg award for important discoveries in medicinally active substances: (1S,3S)-3-amino-4-difluoromethylenyl-1-cyclopentanoic acid (CPP-115), a GABA aminotransferase inactivator and new treatment for drug addiction and infantile spasms.
J Med Chem, 55 (2): 567-75. [PMID:22168767]
5. Thwaites DT, Anderson CM. (2011)
The SLC36 family of proton-coupled amino acid transporters and their potential role in drug transport.
Br J Pharmacol, 164 (7): 1802-16. [PMID:21501141]