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Also known as: 878672-00-5, Rdea594, Rdea 594, Zurampic, Rdea-594, 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-yl)thio)acetic acid

Molecular Formula

C₁₇H₁₄BrN₃O₂S

Molecular Weight

404.3 g/mol

InChI Key

FGQFOYHRJSUHMR-UHFFFAOYSA-N

FDA UNII

73WY698HZ7

Lesinurad is an oral uric acid transporter 1 (URAT1) inhibitor indicated for the treatment of hyperuricemia associated with gout. It reduces serum uric acid concentration through the inhibition of URAT1, an enzyme responsible for reuptake of uric acid from the renal tubule, and OAT4, another uric acid transporter associated with diuretic-induced hyperuricemia. Marketed as the product Zurampic, it is indicated for use in combination with a xanthine oxidase inhibitor for the treatment of hyperuricemia associated with gout in patients who have not achieved target serum uric acid levels with a xanthine oxidase inhibitor alone. In August 2017, a combination oral therapy consisting of lesinurad and [DB00437] was FDA-approved under the brand name Duzallo indicated for the treatment of gout-related hyperuricemia in patients with uncontrolled gout.

Lesinurad is an Urate Transporter 1 Inhibitor. The mechanism of action of lesinurad is as an Urate Transporter 1 Inhibitor, and Cytochrome P450 3A Inducer.

1 2D Structure

Lesinurad

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1,2,4-triazol-3-yl]sulfanyl]acetic acid

2.1.2 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)

2.1.3 InChI Key

FGQFOYHRJSUHMR-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CC1C2=CC=C(C3=CC=CC=C23)N4C(=NN=C4Br)SCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

73WY698HZ7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. ((5-bromo-4-(4-cyclopropyl-1-naphthyl)-4h-1,2,4-triazol-3-yl)sulfanyl)acetic Acid

2. Rdea594

3. Zurampic

2.3.2 Depositor-Supplied Synonyms

1. 878672-00-5

2. Rdea594

3. Rdea 594

4. Zurampic

5. Rdea-594

6. 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-yl)thio)acetic Acid

7. Lesinurad Free Acid

8. (+)-lesinurad

9. (-)-lesinurad

10. Lesinurad, (+)-

11. Lesinurad, (-)-

12. Lesinurad, (4r)-

13. Lesinurad, (4s)-

14. Q59cat99rs

15. 09erp08i3w

16. 73wy698hz7

17. 878672-00-5 (free Acid)

18. 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-ylthio)acetic Acid

19. 2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1,2,4-triazol-3-yl]sulfanyl]acetic Acid

20. 2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-yl]thio]acetic Acid

21. {[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-yl]sulfanyl}acetic Acid

22. 2-(((4r)-5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4h-1,2,4-triazol-3-yl)thio)acetic Acid

23. 2-(((4s)-5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4h-1,2,4-triazol-3-yl)thio)acetic Acid

24. 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-yl]sulfanyl}acetic Acid

25. Acetic Acid, 2-((5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4h-1,2,4-triazol-3-yl)thio)-

26. 1890222-25-9

27. 1890222-26-0

28. Acetic Acid, 2-(((4r)-5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4h-1,2,4-triazol-3-yl)thio)-

29. Acetic Acid, 2-(((4s)-5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4h-1,2,4-triazol-3-yl)thio)-

30. Lesinurad [usan]

31. Lesinurad [usan:inn]

32. Unii-09erp08i3w

33. Zurampic (tn)

34. Lesinurad (rdea594

35. Lesinurad [inn]

36. Lesinurad [mi]

37. Lesinurad (usan/inn)

38. Lesinurad (rdea594)

39. Unii-q59cat99rs

40. Lesinurad [who-dd]

41. Schembl842962

42. Unii-73wy698hz7

43. Gtpl7673

44. Lesinurad [orange Book]

45. Chembl2105720

46. Lesinurad, >=98% (hplc)

47. Bdbm37953

48. Chebi:90929

49. Duzallo Component Lesinurad

50. Dtxsid201026091

51. Hms3874m03

52. Amy27876

53. Bcp06435

54. Ex-a1289

55. Us10093631, Compound Lesinurad

56. Mfcd22572730

57. S4640

58. Zinc84757007

59. Akos027327368

60. Ccg-268685

61. Cs-1389

62. Db11560

63. Sb16705

64. Ac-29310

65. As-56014

66. Hy-15258

67. Rdea 594;rdea-594;rdea594

68. Ft-0776044

69. D09921

70. A857828

71. Q21820633

72. (5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4h-1,2,4-triazol-3-ylthio)acetic Acid

73. 2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4h-1,2,4-triazol-3-ylthio)acetic Acid

74. 2-[[5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4h-1,2,4-triazol-3-yl]thio]-acetic Acid

75. 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3- Yl)sulfanyl)acetic Acid

76. Rdea 594;sodium 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-yl)thio)acetate

2.4 Create Date

2011-10-31

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₄BrN₃O₂S
Molecular Weight	404.3 g/mol
XLogP3	4.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	402.99901 g/mol
Monoisotopic Mass	402.99901 g/mol
Topological Polar Surface Area	93.3 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	479
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For use, in combination with a xanthine oxidase inhibitor, for the treatment of hyperuricemia associated with gout in patients who have not achieved target serum uric acid levels with a xanthine oxidase inhibitor alone.

FDA Label

Zurampic, in combination with a xanthine oxidase inhibitor, is indicated in adults for the adjunctive treatment of hyperuricaemia in gout patients (with or without tophi) who have not achieved target serum uric acid levels with an adequate dose of a xanthine oxidase inhibitor alone.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Dose-dependent reductions in serum uric acid levels and increases in urinary uric acid excretion have been observed following single and multiple oral doses of lesinurad.

5.2 MeSH Pharmacological Classification

Gout Suppressants

Agents that increase uric acid excretion by the kidney (URICOSURIC AGENTS), decrease uric acid production (antihyperuricemics), or alleviate the pain and inflammation of acute attacks of gout. (See all compounds classified as Gout Suppressants.)

Uricosuric Agents

Gout suppressants that act directly on the renal tubule to increase the excretion of uric acid, thus reducing its concentrations in plasma. (See all compounds classified as Uricosuric Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

LESINURAD

5.3.2 FDA UNII

09ERP08I3W

5.3.3 Pharmacological Classes

Mechanisms of Action [MoA] - Cytochrome P450 3A Inducers

5.4 ATC Code

M04AB05

M - Musculo-skeletal system

M04 - Antigout preparations

M04A - Antigout preparations

M04AB - Preparations increasing uric acid excretion

M04AB05 - Lesinurad

5.5 Absorption, Distribution and Excretion

Absorption

Oral lesinurad is rapidly absorbed, reaching maximum plasma concentrations (Cmax) within 14 h following the administration a single 200 mg dose (in either the fed or fasted state).

Route of Elimination

Within 7 days following single dosing of radiolabeled lesinurad, 63% of administered radioactive dose was recovered in urine and 32% of administered radioactive dose was recovered in feces. Most of the radioactivity recovered in urine (> 60% of dose) occurred in the first 24 hours. Unchanged lesinurad in urine accounted for approximately 30% of the dose.

Volume of Distribution

The mean steady state volume of distribution of lesinurad was approximately 20 L following intravenous dosing.

5.6 Metabolism/Metabolites

Lesinurad undergoes oxidative metabolism mainly via the polymorphic cytochrome P450 CYP2C9 enzyme.

5.7 Mechanism of Action

Lesinurad inhibits the activity of uric acid transporter 1 (URAT1) and organic anion transporter 4 (OAT4). URAT1 is a major transporter enzyme responsible for reuptake of uric acid from the renal tubules; inhibition of URAT1 function thereby increases excretion of uric acid.

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DOSAGE - TABLET;ORAL - 200MG

USFDA APPLICATION NUMBER - 207988

DOSAGE - TABLET;ORAL - 200MG;200MG

USFDA APPLICATION NUMBER - 209203

DOSAGE - TABLET;ORAL - 300MG;200MG

USFDA APPLICATION NUMBER - 209203

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DRUG PRODUCT COMPOSITIONS

TABLET;ORAL - 200MG

TABLET;ORAL - 200MG;200MG

TABLET;ORAL - 300MG;200MG

RELATED EXCIPIENT COMPANIES

1 SPI Pharma

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