lesinurad   Click here for help

GtoPdb Ligand ID: 7673

Synonyms: RDEA-594 | RDEA594 | Zurampic®
Approved drug PDB Ligand
lesinurad is an approved drug (FDA (2015), EMA (2016))
Compound class: Synthetic organic
Comment: Lesinurad is an orally available inhibitor of URAT1, the renal transporter that regulates uric acid excretion from the body [1-2].

lesinurad 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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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 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 92.79
Molecular weight 403
XLogP 5.93
No. Lipinski's rules broken 1

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 OC(=O)CSc1nnc(n1c1ccc(c2c1cccc2)C1CC1)Br
Isomeric SMILES OC(=O)CSc1nnc(n1c1ccc(c2c1cccc2)C1CC1)Br
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)
InChI Key FGQFOYHRJSUHMR-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/)
No information available.
Summary of Clinical Use Click here for help
Following the completion of successful Phase 3 clinical trials, the US FDA approved lesinurad as a treatment for the hyperuricaemia which causes the symptoms of gout in December 2015. The EMA followed with approval in April 2016.
Click here to view ClinicalTrials.gov's list of current lesinurad trials.
A fixed dose combination of lesinurad and the xanthine dehydrogenase inhibitor allopurinol (Duzallo®) was FDA and EMA approved in 2017 and 2018 respectively, for the treatment of gout that is not controlled by allopurinol alone.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Lesinurad inhibits the uric acid transporter URAT1 which is expressed in the proximal tubule of the kidney. This reduces re-absorption of uric acid, thereby promoting its renal excretion.
External links Click here for help
For extended ADME data see the following:

Drugs.com
European Medicines Agency (EMA)