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Overview of CAS 328-50-7

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4nro
PharmaCompass
  • Chemistry
4nro
Also known as: 2-ketoglutaric acid, 2-oxopentanedioic acid, 328-50-7, Alpha-ketoglutaric acid, 2-oxoglutarate, Oxoglutaric acid
Molecular Formula
C5H6O5
Molecular Weight
146.098  g/mol
InChI Key
KPGXRSRHYNQIFN-UHFFFAOYSA-N
FDA UNII
8ID597Z82X

Oxogluric acid (α-Ketoglutarate) is not approved for any indication in the world but is an investigational drug in the United States. In the United States a phase I clinical trial is investigating whether oxogluric acid precursors found in nutritional supplements can benefit patients with the metabolic disorder propionic acidemia. Oxogluric acid is sold as a dietary supplement to athletes to improve their performance by helping to remove excess ammonia, but it is not officially approved for this indication and only experimental studies have shown a reduction in ammonia by oxogluric acid in hemodialysis patients. Physiologically, oxogluric acid acts in the Krebs cycle as an intermediate, is involved in transamination reactions during the metabolism of amino acids, forms glutamic acid by combining with ammonia, and reduces nitrogen by combining with it as well. Several experimental studies have also shown that administration of oxogluric acid helped attenuate the decreased synthesis of muscle protein that is often seen post-surgery.
1 2D Structure

4nro

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-oxopentanedioic acid
2.1.2 InChI
InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
2.1.3 InChI Key
KPGXRSRHYNQIFN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CC(=O)O)C(=O)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
8ID597Z82X
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 2-ketoglutaric Acid

2. 2-oxopentanedioic Acid

3. 328-50-7

4. Alpha-ketoglutaric Acid

5. 2-oxoglutarate

6. Oxoglutaric Acid

7. Alpha-ketoglutarate

8. 2-ketoglutarate

9. Alphaketoglutaric Acid

10. Alpha-oxoglutaric Acid

11. 2-oxo-1,5-pentanedioic Acid

12. Pentanedioic Acid, 2-oxo-

13. Oxoglutarate

14. Glutaric Acid, Alpha Keto

15. 2-oxo-glutaric Acid

16. Bis(l-arginin)-2-oxoglutarat

17. Glutaric Acid, 2-oxo-

18. Alpha Ketoglutarate

19. Pentanedioic Acid, Oxo-

20. Ai3-26938

21. Nsc 17391

22. Alpha-ketoglutaric Acid Alpha

23. Unii-8id597z82x

24. Glutaric Acid, 2-oxo- (8ci)

25. 2-oxo-pentanedioic Acid

26. Alpha-keto-glutaric Acid

27. Nsc17391

28. A-ketoglutaric Acid

29. .alpha.-oxoglutaric Acid

30. Einecs 206-330-3

31. .alpha.-ketoglutaric Acid

32. Chembl1686

33. Chebi:30915

34. Kpgxrsrhynqifn-uhfffaoysa-n

35. Mfcd00004165

36. Nsc-17391

37. 378-50-7

38. 17091-15-5

39. 2-oxopentanedionate

40. Dsstox_cid_13179

41. Dsstox_rid_79054

42. Dsstox_gsid_33179

43. Pentanedioic Acid, 2-oxo-, Sodium Salt

44. Pentanedioic Acid, 2-oxo-, Sodium Salt (1:?)

45. 2-ketoglutaricacid

46. 27175-99-1

47. Akg

48. Cas-328-50-7

49. 997-43-3

50. C5h6o5

51. 3ouj

52. 4nro

53. 4oct

54. 4qkd

55. 4usi

56. Keto Glutaric Acid

57. Alpha Ketoglutaric Acid

58. Alpha-oxo-glutaric Acid

59. Ac1q5rhm

60. 22202-68-2

61. Alpha-oxopentanedioic Acid

62. Acmc-1bmr3

63. 2-oxyglutaric Acid

64. 2-oxo-1,5-pentanedioate

65. Bmse000064

66. Bmse000801

67. Bmse000937

68. D09kqz

69. Ac1l18da

70. Schembl7400

71. Ncistruc1_001710

72. Ncistruc2_000215

73. Ksc222o2d

74. Glutaric Acid, .alpha.-keto-

75. Gtpl3636

76. Jsp006044

77. Dtxsid5033179

78. Ctk1c2721

79. Ks-00000cel

80. Molport-001-661-996

81. 8id597z82x

82. Bb_nc-2331

83. Ebd44199

84. Nci17391

85. Pentanedioic Acid, 2-oxo- (9ci)

86. Zinc1532519

87. 997-43-3 (mono-potassium Salt)

88. Tox21_110016

89. Tox21_200918

90. Anw-27470

91. Bbl010614

92. Bdbm50303766

93. Ccg-37641

94. Ncgc00013225

95. Sbb056419

96. Stk002174

97. 15303-07-8 (di-ammonium Salt)

98. 305-72-6 (di-hydrochloride Salt)

99. 17091-15-5 (hydrochloride Salt)

100. Akos000120908

101. Cs-w014352

102. Db02926

103. Db03806

104. Mcule-5148157449

105. Mp-2190

106. Rp21033

107. Rtr-032306

108. Tra0076832

109. Ncgc00013225-01

110. Ncgc00013225-02

111. Ncgc00013225-03

112. Ncgc00013225-04

113. Ncgc00013225-06

114. Ncgc00090946-01

115. Ncgc00090946-02

116. Ncgc00258472-01

117. 22202-68-2 (mono-hydrochloride Salt)

118. 34410-46-3

119. 86248-59-1 (calcium[2:1]salt)

120. Aj-26772

121. Ak-41634

122. Alpha-ketoglutaric Acid, >=99.0% (t)

123. An-23401

124. As-12579

125. Bc206209

126. Br-41634

127. Kb-68907

128. Nci60_001411

129. Sc-16448

130. Ab1011137

131. Db-048280

132. Ls-183918

133. Tr-032306

134. Am20090486

135. Bg00600490

136. Bg01498659

137. Ft-0612734

138. K0005

139. St24032496

140. St45138045

141. C00026

142. 11044-ep2269610a2

143. 11044-ep2277848a1

144. 11044-ep2289510a1

145. 11044-ep2316457a1

146. 11044-ep2316458a1

147. 11044-ep2316825a1

148. 11044-ep2316826a1

149. 11044-ep2316827a1

150. 11044-ep2316828a1

151. Ab00640269-03

152. I04-0237

153. Alpha-ketoglutaric Acid, >=98.5% (naoh, Titration)

154. I14-33772

155. Z57127547

156. F2191-0182

157. 15118487-024f-412c-9995-24e8e6ca72ef

158. Inchi=1/c5h6o5/c6-3(5(9)10)1-2-4(7)8/h1-2h2,(h,7,8)(h,9,10

159. Alpha-ketoglutaric Acid, Bioreagent, Suitable For Cell Culture, Suitable For Insect Cell Culture

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 146.098 g/mol
Molecular Formula C5H6O5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass146.022 g/mol
Monoisotopic Mass146.022 g/mol
Topological Polar Surface Area91.7 A^2
Heavy Atom Count10
Formal Charge0
Complexity171
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

α-α-Ketoglutarate is not approved for any indication in the world but is an investigational drug in the United States. The potential indications for α-Ketoglutarate are in patients with the metabolic disorder propionic acidemia and in trauma patients with muscle loss.


5 Pharmacology and Biochemistry
5.1 Pharmacology

All of the physiological roles of alpha-ketoglutarate have not been determined. What is known is that alpha-keotglutarate is involved in the Krebs cycle, transamination reactions, and promotes muscle synthesis.


5.2 Mechanism of Action

The exact mechanisms of action for α-Ketoglutarate have not yet been elucidated. Some of α-Ketoglutarate’s actions include acting in the Krebs cycle as an intermediate, transamination reactions during the metabolism of amino acids, forming glutamic acid by combining with ammonia, and reducing nitrogen by combining with it as well. Concerning α-Ketoglutarate’s actions with ammonia, it is proposed that α-Ketoglutarate can help patients with propionic academia who have high levels of ammonia and low levels of glutamine/glutamate in their blood. Because endogenous glutamate/glutamine is produced from α-Ketoglutarate, propionic acidemia patients have impaired production of α-Ketoglutarate and supplementation of α-Ketoglutarate should improve the condition of these patients. Several other experimental studies have also shown that administration of α-Ketoglutarate in parenteral nutrition given to post-operative patients helped attenuate the decreased synthesis of muscle protein that is often seen after a surgery. This decreased muscle synthesis is speculated to be due to too low α-Ketoglutarate levels.


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