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2D Structure
Also known as: 65-86-1, 6-carboxyuracil, Oropur, Orodin, Orotonin, Orotyl
Molecular Formula
C5H4N2O4
Molecular Weight
156.10  g/mol
InChI Key
PXQPEWDEAKTCGB-UHFFFAOYSA-N
FDA UNII
61H4T033E5

An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,4-dioxo-1H-pyrimidine-6-carboxylic acid
2.1.2 InChI
InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
2.1.3 InChI Key
PXQPEWDEAKTCGB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=C(NC(=O)NC1=O)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
61H4T033E5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, Orotic

2. Orotate, Potassium

3. Orotate, Sodium

4. Orotate, Zinc

5. Potassium Orotate

6. Sodium Orotate

7. Zinc Orotate

2.3.2 Depositor-Supplied Synonyms

1. 65-86-1

2. 6-carboxyuracil

3. Oropur

4. Orodin

5. Orotonin

6. Orotyl

7. Orotonsan

8. Vitamin B13

9. Whey Factor

10. Oroturic

11. 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic Acid

12. Uracil-6-carboxylic Acid

13. Animal Galactose Factor

14. 6-uracilcarboxylic Acid

15. 2,6-dihydroxypyrimidine-4-carboxylic Acid

16. Molkensaeure

17. Orotsaeure

18. Orotate

19. Uracil-6-carbosaeure

20. 4-pyrimidinecarboxylic Acid, 1,2,3,6-tetrahydro-2,6-dioxo-

21. 2,6-dihydroxy-4-pyrimidinecarboxylic Acid

22. Orotsaeure [german]

23. Acidum Oroticum

24. Acide Orotique

25. Acido Orotico

26. Acide Orotique [french]

27. Acido Orotico [spanish]

28. Acidum Oroticum [latin]

29. Nsc 9791

30. Acide Orotique [inn-french]

31. Acido Orotico [inn-spanish]

32. Acidum Oroticum [inn-latin]

33. 2,4-dioxo-1h-pyrimidine-6-carboxylic Acid

34. Ccris 3929

35. Orotic Acid (6-carboxyuracil)

36. Hsdb 6377

37. Ai3-25478

38. 1,2,3,6-tetrahydro-2,6-dioxopyrimidin-4-carbonsaeure

39. 1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidecarboxylic Acid

40. 6-carboxy-2,4-dihydroxypyrimidine

41. Nsc9791

42. Nsc-9791

43. Poe (12) Tall Oil

44. Mfcd00006027

45. 1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic Acid

46. 61791-00-2

47. Chebi:16742

48. Orotic Acid, Anhydrous

49. Orotic Acid (jan)

50. 61h4t033e5

51. Ncgc00091357-01

52. 1,2,3,4-tetrahydro-2,6-dioxopyrimidine-4-carboxylic Acid

53. Dsstox_cid_5814

54. Orotic Acid [jan]

55. Dsstox_rid_77933

56. Dsstox_gsid_25814

57. Oro

58. Oroticacid

59. Orotic Acid [inn:jan]

60. Cas-65-86-1

61. Orotic Acid (van)

62. Nsc627082

63. Einecs 200-619-8

64. Orotsaure

65. Orotic-acid

66. Orotic Acid [inn:ban:jan]

67. Unii-61h4t033e5

68. Uracil-6-carboxylate

69. Orotic Acid Anhydrous

70. Orotic Acid (8ci)

71. 2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic Acid

72. Orotic-acid-

73. Orotic Acid [mi]

74. Bmse000283

75. Orotic Acid [inn]

76. Orotic Acid [hsdb]

77. Orotic Acid [inci]

78. Schembl20865

79. Orotic Acid [mart.]

80. Mls006011823

81. Orotic Acid(6-carboxyuracil)

82. Orotic Acid (van) (8ci)

83. Orotic Acid [who-dd]

84. Gtpl4690

85. Chembl1235017

86. Dtxsid0025814

87. Ethoxylated Tall Oil Fatty Acids

88. Amy4076

89. Hms3264k19

90. Hms3651i20

91. Pharmakon1600-01504525

92. Bcp09063

93. Hy-n0157

94. Zinc1408068

95. Tox21_111121

96. Tox21_201104

97. Bbl013050

98. Nsc758903

99. S2336

100. Stk301771

101. Stk629991

102. Akos000119689

103. Akos004115502

104. Tox21_111121_1

105. Ccg-213952

106. Db02262

107. Nsc-758903

108. Sb55525

109. Ncgc00091357-02

110. Ncgc00188943-01

111. Ncgc00188943-03

112. Ncgc00188943-04

113. Ncgc00258656-01

114. Smr001550463

115. Sy006030

116. Ts-00078

117. 2,6-dihydroxy-pyrimidin-4-carboxylic Acid

118. Sbi-0207042.p001

119. 2,6-dihydroxy-pyrimidine-4-carboxylic Acid

120. Db-073669

121. 4-pyrimidinecarboxylic Acid, 2,6-dihydroxy-

122. A8909

123. B1147

124. Bb 0242405

125. Ft-0603612

126. Ft-0648914

127. O0065

128. Orotic Acid, >=98% (titration), Anhydrous

129. Sw219707-1

130. C00295

131. D00055

132. D70614

133. Ab00373897_03

134. Ab-323/25048164

135. Q425536

136. Sr-01000872754

137. Sr-01000872754-1

138. W-104782

139. F2191-0093

140. 2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-ca Rboxylic Acid

141. 37c71c07-0d69-452c-8c54-7d01be02c146

142. 4-pyrimidinecarboxylic Acid, 1,2,3,6-tetrahydro-2,6-dioxo- (9ci)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 156.10 g/mol
Molecular Formula C5H4N2O4
XLogP3-1.4
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass156.01710661 g/mol
Monoisotopic Mass156.01710661 g/mol
Topological Polar Surface Area95.5 Ų
Heavy Atom Count11
Formal Charge0
Complexity268
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 Therapeutic Uses

Uricosuric

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1230


This study deals with the potential therapeutic effect of orotic acid (OA) and Mg Orotate (MgO) on myocardial degeneration and the development of congestive heart failure in cardiomyopathic (CM) hamsters of the UM-X7.1 line. Two major age groups (group I, < 30 days and group II, > 180 days old) were used in these experiments, which lasted 30 and 50 days, respectively; the orotic salts were incorporated (10%) into Purina Lab Chow given ad libitum. Macroscopic and microscopic assessment of pathologic changes together with ECG recordings revealed that MgO treatment significantly reduces myocardial damage, especially the severity of calcific changes. ECG recordings clearly demonstrated a significant shortening of QTc and PR intervals, resulting in partial electrical stabilization of failing hearts, with a significant delay in systemic congestive changes. The prevention of heart lesions was less evident in animals receiving OA, but both preparations proved to be equally efficient in prolonging survival of the CM hamsters.

PMID:9794093 Jasmin G, Proschek L; Cardiovasc Drugs Ther 12 (Suppl 2): 189-95 (1998)


... Three studies were performed: (1) The time course of changes in tissue and plasma concentrations of pyrimidine compounds was examined in unoperated rats after the administration of 100 mg/kg OA. (2) Rats were given OA (30 mg/kg/d) for 2 days after experimental infarction, and tissue and plasma pyrimidine concentrations were examined; the hearts were removed for perfusion in the isolated working rat heart model (37 degrees C), subjected to 30 minutes of global ischemia, and recovery of function was assessed. AN content was assessed in the noninfarcted myocardium before and after ischemia. Isolated hearts were subjected to 30 minutes of hypoxic perfusion and the effect of adding 17 microM uridine to the perfusate was examined. Study 1 showed that OA administration produced an increase in hepatic uridine and cytidine, followed by increased plasma uridine and cytidine (cytidine, +55%, P < 0.001; uridine, +124%, P = 0.011). Myocardial uracil nucleotides increased temporarily after 4 hours (+21%, P < 0.01). In infarcted hearts after 2 days of OA administration, there were no significant changes in myocardial uracil or cytosine nucleotides or total RNA. Infarction significantly reduced functional recovery after global ischemia (sham = 62%; infarct = 26% of preischemic level; P < 0.05). OA improved the recovery of preischemic function by 133% (P < 0.05) in infarcted, but not sham-operated, hearts. Preischemic ATP and total adenine nucleotides (TAN) were decreased in the surviving myocardium of infarcted hearts (ATP reduced from 21.7 +/- 0.8 to 14.7 +/- 0.7 mumol/g dry wt, P < 0.001; TAN decreased from 30.3 +/- 0.8 to 22.4 +/- 1.1 mumol/g dry wt, P < 0.001). OA treatment prevented these reductions. Study 3 showed that uridine improved myocardial ATP and TAN levels, and decreased purine loss in hypoxic hearts. The increased AN levels were accompanied by evidence of enhancement of anerobic glycolysis.

PMID:9794090 Rosenfeldt FL et al; Cardiovasc Drugs Ther 12 (Suppl. 2): 159-70 (1998)


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

[14C]Orotic acid was rapidly distributed in blood after both i.p. and s.c. injection but was not completely absorbed from the peritoneal cavity until 20 min after injection. S.c. injection should be an acceptable alternative to i.p. injection although the incorporation into the liver acid soluble- and RNA-fractions was somewhat delayed after the s.c. injection.

PMID:858350 Engelbrecht C et al; Experientia 33 (3): 302-4 (1977)


5.2 Metabolism/Metabolites

... The aim of this work was to investigate whether orotate is differently metabolized in gut and in liver thus explaining the lack of effect on the intestinal lipoproteins secretion. Multienzyme complex (complex U) was found in appreciable amounts in rat, mouse and rabbit livers; the intestinal mucosa of the two last species contains a much lower level of multienzyme complex whereas in rat intestine its activity cannot be detected. Indeed, radioactive aspartate and orotate were not incorporated into intestinal cells RNA. The absence of orotate metabolisation by lack of orotate phosphoribosyltransferase and orotidine 5'-phosphate decarboxylase activity in rat intestine would explain why this organ, in contrast to the liver, is protected against disturbances of nucleotide metabolism and lipoproteins secretion induced by orotic-acid-supplemented diets.

PMID:7297564 Raisonnier A et al; Eur J Biochem 118 (3): 565-9 (1981)