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Details

Stereochemistry RACEMIC
Molecular Formula C17H14BrN3O2S
Molecular Weight 404.281
Optical Activity ( + / - )
Additional Stereochemistry Yes
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0
Stereo Comments AXIAL, RACEMIC

SHOW SMILES / InChI
Structure of LESINURAD

SMILES

OC(=O)CSC1=NN=C(Br)N1C2=C3C=CC=CC3=C(C=C2)C4CC4

InChI

InChIKey=FGQFOYHRJSUHMR-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C17H14BrN3O2S
Molecular Weight 404.281
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Unknown
123738
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:16:11 UTC 2023
Edited
by admin
on Fri Dec 15 19:16:11 UTC 2023
Record UNII
09ERP08I3W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LESINURAD
DASH   INN   USAN   WHO-DD  
INN   USAN  
Official Name English
lesinurad [INN]
Common Name English
RDEA 594
Code English
LESINURAD [MI]
Common Name English
LESINURAD [ORANGE BOOK]
Common Name English
RDEA594
Code English
2-((5-BROMO-4-(4-CYCLOPROPYLNAPHTHALEN-1-YL)-4H-1,2,4-TRIAZOL-3- YL)SULFANYL)ACETIC ACID
Systematic Name English
ZURAMPIC
Brand Name English
ACETIC ACID, 2-((5-BROMO-4-(4-CYCLOPROPYL-1-NAPHTHALENYL)-4H-1,2,4-TRIAZOL-3-YL)THIO)-
Common Name English
LESINURAD [USAN]
Common Name English
DUZALLO COMPONENT LESINURAD
Brand Name English
RDEA-594
Code English
Lesinurad [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC M04AB05
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
NDF-RT N0000192341
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C175109
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
RXCUI
1731031
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105720
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
MERCK INDEX
m11920
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
DRUG BANK
DB11560
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
DRUG CENTRAL
5075
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID201026091
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
CAS
878672-00-5
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
CHEBI
90929
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
WIKIPEDIA
Lesinurad
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
EVMPD
SUB93370
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
NDF-RT
N0000190118
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY Cytochrome P450 3A Inducers [MoA]
USAN
WW-158
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
FDA UNII
09ERP08I3W
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
SMS_ID
100000141557
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
NDF-RT
N0000192340
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY Urate Transporter 1 Inhibitors [MoA]
PUBCHEM
53465279
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
INN
9345
Created by admin on Fri Dec 15 19:16:11 UTC 2023 , Edited by admin on Fri Dec 15 19:16:11 UTC 2023
PRIMARY
Related Record Type Details
OATP1B1
TRANSPORTER -> INHIBITOR
Based on in vitro studies, lesinurad is a weak inhibitor of OATP1B1, OCT1, OAT1, and OAT3.
WEAK
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> NON-SUBSTRATE
CYTOCHROME P450 2C9
METABOLIC ENZYME -> SUBSTRATE
MAJOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INDUCER
WEAK
OCT-1
TRANSPORTER -> INHIBITOR
Based on in vitro studies, lesinurad is a weak inhibitor of OATP1B1, OCT1, OAT1, and OAT3.
WEAK
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MINOR
Structure of LESINURAD SODIUM
SALT/SOLVATE -> PARENT
CYTOCHROME P450 1A1
METABOLIC ENZYME -> SUBSTRATE
MINOR
OAT-1
TRANSPORTER -> SUBSTRATE
Based on in vitro studies, lesinurad is a substrate of OAT1 and OAT3.
OATL-4
TRANSPORTER -> INHIBITOR
IC50
Structure of LESINURAD
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
MINOR
OAT-4
TARGET -> INHIBITOR
inhibits the transport of [14C]uric acid into human embryonic kidney-293 cells expressing OAT4
IC50
OAT-3
TRANSPORTER -> INHIBITOR
Based on in vitro studies, lesinurad is a weak inhibitor of OATP1B1, OCT1, OAT1, and OAT3.
WEAK
OATL-4
TARGET -> INHIBITOR
IC50
OAT-3
TRANSPORTER -> SUBSTRATE
Based on in vitro studies, lesinurad is a substrate of OAT1 and OAT3.
Structure of LESINURAD, (4R)-
ENANTIOMER -> RACEMATE
OAT-1
TRANSPORTER -> INHIBITOR
Based on in vitro studies, lesinurad is a weak inhibitor of OATP1B1, OCT1, OAT1, and OAT3.
WEAK
Structure of LESINURAD
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of LESINURAD, (4S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of DESCYCLOPROPYL-(1-HYDROXYCYCLOPROPYL)LESINURAD
METABOLITE -> PARENT
AMOUNT EXCRETED
FECAL
Structure of 2-(4-(1-CYCLOPROPYLNAPHTHALEN-4-YL)-4H-1,2,4-TRIAZOL-3-YLTHIO)ACETIC ACID
METABOLITE -> PARENT
AMOUNT EXCRETED
FECAL
Structure of 5,6-DIHYDRO-5,6-DIHYDROXY LESINURAD
METABOLITE -> PARENT
AMOUNT EXCRETED
FECAL
Structure of 2-(4-(1-CYCLOPROPYLNAPHTHALEN-4-YL)-4H-1,2,4-TRIAZOL-3-YLTHIO)ACETIC ACID
METABOLITE -> PARENT
AMOUNT EXCRETED
URINE
Structure of 5,6-DIHYDRO-5,6-DIHYDROXY LESINURAD
METABOLITE -> PARENT
PLASMA
Structure of 5,6-DIHYDRO-5,6-DIHYDROXY LESINURAD
METABOLITE -> PARENT
AMOUNT EXCRETED
URINE
Structure of DESCYCLOPROPYL-(1-HYDROXYCYCLOPROPYL)LESINURAD
METABOLITE -> PARENT
AMOUNT EXCRETED
URINE
Structure of DESCYCLOPROPYL-(1-HYDROXYCYCLOPROPYL)LESINURAD
METABOLITE -> PARENT
PLASMA
Structure of 2-((4-(4-(1-HYDROXYCYCLOPROPYL)-1-NAPHTHYL)-1,2,4-TRIAZOL-3-YL)SULFANYL)ACETIC ACID
METABOLITE -> PARENT
AMOUNT EXCRETED
FECAL
Related Record Type Details
Structure of LESINURAD
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC INTRAVENOUS ADMINISTRATION

SINGLE DOSE

Tmax PHARMACOKINETIC FED CONDITION

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