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Details

Stereochemistry ACHIRAL
Molecular Formula C20H16N2O2S
Molecular Weight 348.418
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VERINURAD

SMILES

CC(C)(SC1=C(C=NC=C1)C2=C3C=CC=CC3=C(C=C2)C#N)C(O)=O

InChI

InChIKey=YYBOLPLTQDKXPM-UHFFFAOYSA-N
InChI=1S/C20H16N2O2S/c1-20(2,19(23)24)25-18-9-10-22-12-17(18)16-8-7-13(11-21)14-5-3-4-6-15(14)16/h3-10,12H,1-2H3,(H,23,24)

HIDE SMILES / InChI

Molecular Formula C20H16N2O2S
Molecular Weight 348.418
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Verinurad (RDEA3170) is a selective uric acid reabsorption inhibitor in clinical development for the treatment of gout and asymptomatic hyperuricemia. Verinurad specifically inhibits URAT1 with a potency of 25 nM. High affinity inhibition of uric acid transport requires URAT1 residues Cys-32, Ser-35, Phe-365 and Ile-481. Unlike other available uricosuric agents, the requirement for Cys-32 is unique to verinurad. Verinurad doses as low as 2.5 mg produce significant sUA lowering in humans, and this greater reduction in sUA may lead to improved outcomes and medical benefits for patients with gout. Verinurad in monotherapy studies has been associated with increased urinary uric acid concentrations and low rates of serum creatinine (sCr) elevation. Verinurad combined with febuxostat decreased sUA dose-dependently while maintaining uric acid excretion similar to baseline. All dose combinations of verinurad and febuxostat were generally well tolerated.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
25.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Pharmacodynamic and pharmacokinetic effects and safety of verinurad in combination with febuxostat in adults with gout: a phase IIa, open-label study.
2018
Effect of Renal Impairment on the Pharmacokinetics and Pharmacodynamics of Verinurad, a Selective Uric Acid Reabsorption Inhibitor.
2018 Aug
Verinurad combined with febuxostat in Japanese adults with gout or asymptomatic hyperuricaemia: a phase 2a, open-label study.
2018 Sep 1

Sample Use Guides

In Vivo Use Guide
Panels of eight male subjects received a single oral dose of verinurad or placebo in either a fasted or fed state; panels of 10-12 male subjects received ascending doses of once-daily verinurad or placebo in a fasted state for 10 days. Verinurad reduced serum urate levels by up to 62% (40 mg, single dose) and 61% (10 mg, multiple dose). The increase in urinary excretion of uric acid was greatest in the first 6 hours after dosing and was still evident ≥24 hours for verinurad doses ≥2 mg. Verinurad was well tolerated at all doses.
Route of Administration: Oral
In Vitro Use Guide
Verinurad specifically inhibits URAT1 with a potency of 25 nM.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:27:19 UTC 2019
Edited
by admin
on Mon Oct 21 20:27:19 UTC 2019
Record UNII
12WJ62D047
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VERINURAD
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
VERINURAD [INN]
Common Name English
VERINURAD [USAN]
Common Name English
PROPANOIC ACID, 2-((3-(4-CYANO-1-NAPHTHALENYL)-4-PYRIDINYL)THIO)-2-METHYL-
Systematic Name English
VERINURAD [WHO-DD]
Common Name English
RDEA-3170
Code English
RDEA3170
Code English
Classification Tree Code System Code
NCI_THESAURUS C921
Created by admin on Mon Oct 21 20:27:19 UTC 2019 , Edited by admin on Mon Oct 21 20:27:19 UTC 2019
Code System Code Type Description
CAS
1352792-74-5
Created by admin on Mon Oct 21 20:27:19 UTC 2019 , Edited by admin on Mon Oct 21 20:27:19 UTC 2019
PRIMARY
NCI_THESAURUS
C152863
Created by admin on Mon Oct 21 20:27:19 UTC 2019 , Edited by admin on Mon Oct 21 20:27:19 UTC 2019
PRIMARY
PUBCHEM
54767229
Created by admin on Mon Oct 21 20:27:19 UTC 2019 , Edited by admin on Mon Oct 21 20:27:19 UTC 2019
PRIMARY
ChEMBL
CHEMBL3707347
Created by admin on Mon Oct 21 20:27:19 UTC 2019 , Edited by admin on Mon Oct 21 20:27:19 UTC 2019
PRIMARY
INN
9938
Created by admin on Mon Oct 21 20:27:19 UTC 2019 , Edited by admin on Mon Oct 21 20:27:19 UTC 2019
PRIMARY
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METABOLIC ENZYME -> SUBSTRATE
MINOR
METABOLIC ENZYME -> SUBSTRATE
MINOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
METABOLIC ENZYME -> SUBSTRATE
MINOR
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE

Biological Half-life PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION

Volume of Distribution PHARMACOKINETIC