lesinurad 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
urate transporter inhibitors	5075	878672-00-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: lesinurad zurampic RDEA594 Sodium RDEA594	Lesinurad reduces serum uric acid levels by inhibiting the function of transporter proteins involved in uric acid reabsorption in the kidney. Lesinurad inhibited the function of two apical transporters responsible for uric acid reabsorption, uric acid transporter 1 (URAT1) and organic anion transporter 4 (OAT4), with IC50 values of 7.3 and 3.7 μM, respectively. URAT1 is responsible for the majority of the reabsorption of filtered uric acid from the renal tubular lumen. OAT4 is a uric acid transporter associated with diuretic-induced hyperuricemia. Molecular weight: 404.28 Formula: C17H14BrN3O2S CLOGP: 4.01 LIPINSKI: 0 HAC: 5 HDO: 1 TPSA: 68.01 ALOGS: -4.72 ROTB: 4 Status: OFM Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

lesinurad
zurampic
RDEA594 Sodium
RDEA594

Lesinurad reduces serum uric acid levels by inhibiting the function of transporter proteins involved in uric acid reabsorption in the kidney. Lesinurad inhibited the function of two apical transporters responsible for uric acid reabsorption, uric acid transporter 1 (URAT1) and organic anion transporter 4 (OAT4), with IC50 values of 7.3 and 3.7 μM, respectively. URAT1 is responsible for the majority of the reabsorption of filtered uric acid from the renal tubular lumen. OAT4 is a uric acid transporter associated with diuretic-induced hyperuricemia.

Molecular weight: 404.28
Formula: C17H14BrN3O2S
CLOGP: 4.01
LIPINSKI: 0
HAC: 5
HDO: 1
TPSA: 68.01
ALOGS: -4.72
ROTB: 4

Status: OFM

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.20	g	O

ADMET properties:

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Property	Value	Reference
t_half (Half-life)	5 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Hosey CM, Chan R, Benet LZ
CL (Clearance)	1.43 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.29 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.02 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.01 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
Dec. 22, 2015	FDA	ARDEA BIOSCIENCES INC
Feb. 18, 2016	EMA	AstraZeneca AB

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	M04AB05	MUSCULO-SKELETAL SYSTEM ANTIGOUT PREPARATIONS ANTIGOUT PREPARATIONS Preparations increasing uric acid excretion
CHEBI has role	CHEBI:35841	uricosuric drugs
FDA EPC	N0000192341	Urate Transporter 1 Inhibitor
FDA MoA	N0000190118	Cytochrome P450 3A Inducers
FDA MoA	N0000192340	Urate Transporter 1 Inhibitors
MeSH PA	D018501	Antirheumatic Agents
MeSH PA	D006074	Gout Suppressants
MeSH PA	D014528	Uricosuric Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Hyperuricemia	indication	35885006	DOID:1920

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	3.5	acidic
pKa2	1.05	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
200MG	ZURAMPIC	IRONWOOD PHARMS INC	N207988	Dec. 22, 2015	DISCN	TABLET	ORAL	10183012	Nov. 26, 2028	TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A XANTHINE OXIDASE INHIBITOR ALONE
200MG	ZURAMPIC	IRONWOOD PHARMS INC	N207988	Dec. 22, 2015	DISCN	TABLET	ORAL	8283369	Nov. 26, 2028	ACHIEVING A THERAPEUTIC BENEFIT IN A SUBJECT WITH GOUT
200MG	ZURAMPIC	IRONWOOD PHARMS INC	N207988	Dec. 22, 2015	DISCN	TABLET	ORAL	8283369	Nov. 26, 2028	TREATMENT OF GOUT
200MG	ZURAMPIC	IRONWOOD PHARMS INC	N207988	Dec. 22, 2015	DISCN	TABLET	ORAL	8546437	April 29, 2029	TREATMENT OF HYPERURICEMIA
200MG	ZURAMPIC	IRONWOOD PHARMS INC	N207988	Dec. 22, 2015	DISCN	TABLET	ORAL	8084483	Aug. 17, 2029	REDUCTION OF SERUM URIC ACID LEVELS
200MG	ZURAMPIC	IRONWOOD PHARMS INC	N207988	Dec. 22, 2015	DISCN	TABLET	ORAL	8357713	Dec. 22, 2029	REDUCTION OF SERUM URIC ACID LEVELS
200MG	ZURAMPIC	IRONWOOD PHARMS INC	N207988	Dec. 22, 2015	DISCN	TABLET	ORAL	8357713	Dec. 22, 2029	TREATMENT OF GOUT
200MG	ZURAMPIC	IRONWOOD PHARMS INC	N207988	Dec. 22, 2015	DISCN	TABLET	ORAL	8357713	Dec. 22, 2029	TREATMENT OF HYPERURICEMIA
200MG	ZURAMPIC	IRONWOOD PHARMS INC	N207988	Dec. 22, 2015	DISCN	TABLET	ORAL	9216179	Aug. 1, 2031	COADMINISTERING WITH ALLOPURINOL TO REDUCE SERUM URIC ACID (SUA) BELOW 4 MG/DL; BELOW 6MG/DL IN PATIENTS HAVING URIC ACID DEPOSITS; AND/OR BELOW 6MG/DL WITH SUA INTRADAY CHANGE MORE THAN 50% AND/OR ADVERSE EVENT RATE LESS THAN 15%
200MG	ZURAMPIC	IRONWOOD PHARMS INC	N207988	Dec. 22, 2015	DISCN	TABLET	ORAL	9956205	Dec. 28, 2031	TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A XANTHINE OXIDASE INHIBITOR ALONE

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Solute carrier family 22 member 12	Transporter	Q96S37	S22AC_HUMAN	INHIBITOR	IC50	5.14		DRUG LABEL	DRUG LABEL
Solute carrier family 22 member 11	Transporter	Q9NSA0	S22AB_HUMAN	INHIBITOR	IC50	5.43		DRUG LABEL

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External reference:

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ID	Source
016642	NDDF
09ERP08I3W	UNII
1731031	RXNORM
237601	MMSL
31385	MMSL
4036022	VANDF
53465279	PUBCHEM_CID
715259003	SNOMEDCT_US
715745009	SNOMEDCT_US
7673	IUPHAR_LIGAND_ID

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Pharmaceutical products:

None