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    Uric Acid

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 69-93-2, Urate, Lithic acid, 2,6,8-trioxypurine, 2,6,8-trihydroxypurine, 8-hydroxyxanthine
    Molecular Formula
    C5H4N4O3
    Molecular Weight
    168.11  g/mol
    InChI Key
    LEHOTFFKMJEONL-UHFFFAOYSA-N
    FDA UNII
    268B43MJ25
    An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    7,9-dihydro-3H-purine-2,6,8-trione
    2.1.2 InChI
    InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)
    2.1.3 InChI Key
    LEHOTFFKMJEONL-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C12=C(NC(=O)N1)NC(=O)NC2=O
    2.2 Other Identifiers
    2.2.1 UNII
    268B43MJ25
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2,6,8-trihydroxypurine

    2. Acid Urate, Ammonium

    3. Acid Urate, Sodium

    4. Acid, Uric

    5. Ammonium Acid Urate

    6. Monohydrate, Monosodium Urate

    7. Monohydrate, Sodium Urate

    8. Monosodium Urate

    9. Monosodium Urate Monohydrate

    10. Potassium Urate

    11. Sodium Acid Urate

    12. Sodium Acid Urate Monohydrate

    13. Sodium Urate

    14. Sodium Urate Monohydrate

    15. Trioxopurine

    16. Urate

    17. Urate Monohydrate, Monosodium

    18. Urate Monohydrate, Sodium

    19. Urate, Ammonium Acid

    20. Urate, Monosodium

    21. Urate, Potassium

    22. Urate, Sodium

    23. Urate, Sodium Acid

    2.3.2 Depositor-Supplied Synonyms

    1. 69-93-2

    2. Urate

    3. Lithic Acid

    4. 2,6,8-trioxypurine

    5. 2,6,8-trihydroxypurine

    6. 8-hydroxyxanthine

    7. 7,9-dihydro-1h-purine-2,6,8(3h)-trione

    8. 2,6,8-trioxopurine

    9. 1h-purine-2,6,8-triol

    10. 1h-purine-2,6,8(3h)-trione, 7,9-dihydro-

    11. Purine-2,6,8(1h,3h,9h)-trione

    12. 7,9-dihydro-3h-purine-2,6,8-trione

    13. Uricum Acidum

    14. Ai3-15432

    15. 2,3,6,7,8,9-hexahydro-1h-purine-2,6,8-trione

    16. Nsc 3975

    17. 1h-purine-2,6,8(3h,7h,9h)-trione

    18. Nsc-3975

    19. Mfcd00005712

    20. Idelalisib Metabolite M54

    21. Chembl792

    22. 9h-purine-2,6,8-triol

    23. Chebi:17775

    24. 268b43mj25

    25. 2,6-dihydroxy-7,9-dihydropurin-8-one

    26. Ncgc00181032-01

    27. 8-hydroxy-3,9-dihydro-1h-purine-2,6-dione

    28. 6,8-dioxo-6,7,8,9-tetrahydro-1h-purin-2-olate

    29. Trioxopurine

    30. Urc

    31. Einecs 200-720-7

    32. Lithate

    33. Hypoxanthinediol

    34. Uric-acid

    35. Unii-268b43mj25

    36. 2,8-trioxopurine

    37. 2,8-trioxypurine

    38. 8hx

    39. Uric Acid (8ci)

    40. 2,8-trihydroxypurine

    41. 1l5s

    42. 2,6,8-trihydroxypurin

    43. Purine-2,6,8-triol

    44. 1h-purine-2,8-triol

    45. Uric Acid, 99.0%

    46. Uric Acid [mi]

    47. Uric Acid [inci]

    48. Bmse000126

    49. Schembl7933

    50. 7h-purine-2,6,8-triol

    51. Dsstox_cid_22508

    52. Dsstox_rid_80044

    53. Dsstox_gsid_42508

    54. Uricum Acidum [hpus]

    55. (s)-3-aminoquinuclidine Hcl

    56. Gtpl4731

    57. Dtxsid3042508

    58. Schembl15777793

    59. Schembl17081907

    60. Chebi:46811

    61. Chebi:46814

    62. Chebi:46817

    63. Chebi:46823

    64. Chebi:62589

    65. Nsc3975

    66. Uric Acid, >=99%, Crystalline

    67. Hms3604n17

    68. Amy23430

    69. Bcp28980

    70. Hy-b2130

    71. Purine-2,8(1h,3h,9h)-trione

    72. Zinc2041003

    73. Tox21_113563

    74. Bdbm50325824

    75. S3955

    76. Stl185577

    77. Akos000118731

    78. Purine-3,6,8(1h,3h,9h)-trione

    79. Ccg-339700

    80. Db08844

    81. Uric Acid, Nist(r) Srm(r) 913b

    82. Cas-69-93-2

    83. Purine-2,6,8-(1h,3h,9h)-trione

    84. Uric Acid, Bioxtra, >=99% (hplc)

    85. As-56119

    86. Sy057305

    87. 6-hydroxy-1h-purine-2,8(7h,9h)-dione

    88. Db-055359

    89. 2,6,8-trioxypurine;2,6,8-trihydroxypurine

    90. 2,6-dihydroxy-7,9-dihydro-8h-purin-8-one

    91. Cs-0020287

    92. Ft-0631301

    93. U0018

    94. 1h-purine-2,8(3h)-trione, 7,9-dihydro-

    95. 7,9-dihydro-3h-purine-2,6,8-trione(urate)

    96. C00366

    97. U-6050

    98. 1h-purine-2,6,8-triol 2,6,8-trihydroxypurine

    99. 7,9-dihydro-3h-purine-2,6,8-trione(uric Acid)

    100. A866713

    101. Q105522

    102. Sr-01000945208

    103. Sr-01000945208-1

    104. 565ff3af-8afa-4ee9-9fc4-6b119784a5bb

    105. 1h-purine-2,6,8(3h)-trione, 7,9-dihydro- (9ci)

    106. Z1318255135

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 168.11 g/mol
    Molecular Formula C5H4N4O3
    XLogP3-1.9
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count0
    Exact Mass168.02834000 g/mol
    Monoisotopic Mass168.02834000 g/mol
    Topological Polar Surface Area99.3 Ų
    Heavy Atom Count12
    Formal Charge0
    Complexity332
    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

    At present (August 2013), there is no approved indication for uric acid. The potential therapeutic use for uric acid is as an adjunct in acute ischemic stroke.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Uric acid is a strong reducing agent (donates electrons) and an antioxidant. Normally in humans, one of the main antioxidants in plasma is uric acid. Several animal studies have found that animals given exogenous uric acid within 3 hours after a stroke had decreased infarct volume, improved neurologic function, and diminished inflammatory responses providing evidence for the neuroprotective effects of uric acid. In some early human studies, uric acid has so far shown similar neuroprotective effects, in both the cortex and subcortex areas, due to its antioxidant effects such as decreased lipid peroxidation, and there appears to be no significant toxicities.

    5.2 MeSH Pharmacological Classification

    Antioxidants

    Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

    5.3 Absorption, Distribution and Excretion

    Route of Elimination

    Uric acid is eliminated by the kidneys.

    5.4 Metabolism/Metabolites

    In higher primates and humans, the enzyme, uricase, is absent, and thus uric acid is not further metabolized and is excreted. In all other mammals, uric acid is metabolized by uricase to allantoin, which is then excreted.

    5.5 Mechanism of Action

    The exact mechanism of action for uric acid's antioxidant effects have not yet been elucidated.