VIGABATRIN

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Search structure


Trade Names	SABRIL VIGABATRIN VIGADRONE
Synonyms	5-hexenoic acid, 4-amino- CPP-109 Gamma vinyl gaba Gamma-vinyl gaba MDL 71,754 MDL-71754 RMI-71754 Sabril Vigabatrin Vinyl gamma-aminobutyric acid
Status
Molecule Category	UNKNOWN
ATC	N03AG04
UNII	GR120KRT6K
EPA CompTox	DTXSID4041153


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	PJDFLNIOAUIZSL-UHFFFAOYSA-N
Smiles	C=CC(N)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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C6H11NO2
Molecular Weight	129.16
AlogP	0.36
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	4.0
Polar Surface Area	63.32
Molecular species	ZWITTERION
Aromatic Rings	0.0
Heavy Atoms	9.0

Bioactivity

Mechanism of Action	Action	Reference
Gamma-amino-N-butyrate transaminase inhibitor	INHIBITOR	FDA PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Transferase	-	39720	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	79

Assay Description	Organism	Bioactivity	Reference
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	78.69 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	94.41 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	36.65 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	5.34 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.06 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.06 %

Cross References

Resources	Reference
ChEBI	63638
ChEMBL	CHEMBL89598
DrugBank	DB01080
DrugCentral	2819
FDA SRS	GR120KRT6K
Human Metabolome Database	HMDB0015212
Guide to Pharmacology	4821
KEGG	C07500
PharmGKB	PA10231
PubChem	5665
SureChEMBL	SCHEMBL26714
ZINC	ZINC00403618

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).