LESINURAD

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Search structure


Trade Names	ZURAMPIC
Synonyms	Lesinurad RDEA 594 RDEA-594 RDEA594 Zurampic
Status
Molecule Category	Free-form
ATC	M04AB05
UNII	09ERP08I3W


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

Structure


InChI Key	FGQFOYHRJSUHMR-UHFFFAOYSA-N
Smiles	O=C(O)CSc1nnc(Br)n1-c1ccc(C2CC2)c2ccccc12
InChI	InChI=1S/C17H14BrN3O2S/c18-16-19-20-17(24-9-15(22)23)21(16)14-8-7-11(10-5-6-10)12-3-1-2-4-13(12)14/h1-4,7-8,10H,5-6,9H2,(H,22,23)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C17H14BrN3O2S
Molecular Weight	404.29
AlogP	4.24
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	5.0
Polar Surface Area	68.01
Molecular species	ACID
Aromatic Rings	3.0
Heavy Atoms	24.0

Bioactivity

Mechanism of Action	Action	Reference
Solute carrier family 22 member 12 inhibitor	INHIBITOR	FDA


Protein: Solute carrier family 22 member 12 Description: Solute carrier family 22 member 12 Organism : Homo sapiens Q96S37 ENSG00000197891

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2	-	17300-39300	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19	-	10600-61700	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9	-	31200-78700	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6	-	32600-92100	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4	-	31000-74400	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters	-	3530-15100	-	-	-

Assay Description	Organism	Bioactivity	Reference
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	-2.12 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	3.42 %
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	0.16 %		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	0.16 %

Cross References

Resources	Reference
ChEBI	90929
ChEMBL	CHEMBL2105720
DrugBank	DB11560
DrugCentral	5075
FDA SRS	09ERP08I3W
Guide to Pharmacology	7673
PharmGKB	PA166160006
PubChem	53465279
SureChEMBL	SCHEMBL842962
ZINC	ZINC000084757007

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).