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    Chemistry

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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
    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 Weight 404.3 g/mol
    Molecular Formula C17H14BrN3O2S
    XLogP34.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count5
    Exact Mass402.99901 g/mol
    Monoisotopic Mass402.99901 g/mol
    Topological Polar Surface Area93.3 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity479
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.

    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET;ORAL - 200MG

    USFDA APPLICATION NUMBER - 207988

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    DOSAGE - TABLET;ORAL - 200MG;200MG

    USFDA APPLICATION NUMBER - 209203

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    DOSAGE - TABLET;ORAL - 300MG;200MG

    USFDA APPLICATION NUMBER - 209203

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