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Uric Acid

Synopsis, Chemistry

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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

Uric Acid

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 Formula	C₅H₄N₄O₃
Molecular Weight	168.11 g/mol
XLogP3	-1.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Exact Mass	168.02834000 g/mol
Monoisotopic Mass	168.02834000 g/mol
Topological Polar Surface Area	99.3 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	332
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

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.