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L-Pyroglutamic Acid

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Chemistry

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Also known as: 98-79-3, Pidolic acid, Pyroglutamic acid, 5-oxoproline, 5-oxo-l-proline, Pyroglutamate

Molecular Formula

C₅H₇NO₃

Molecular Weight

129.11 g/mol

InChI Key

ODHCTXKNWHHXJC-VKHMYHEASA-N

FDA UNII

SZB83O1W42

A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.

1 2D Structure

L-Pyroglutamic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-5-oxopyrrolidine-2-carboxylic acid

2.1.2 InChI

InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1

2.1.3 InChI Key

ODHCTXKNWHHXJC-VKHMYHEASA-N

2.1.4 Canonical SMILES

C1CC(=O)NC1C(=O)O

2.1.5 Isomeric SMILES

C1CC(=O)N[C@@H]1C(=O)O

2.2 Other Identifiers

2.2.1 UNII

SZB83O1W42

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-ketoproline

2. 5-oxoproline

3. 5-oxopyrrolidine-2-carboxylic Acid

4. Magnesium Pidolate

5. Pidolate, Magnesium

6. Pidolic Acid

7. Pyroglutamate

8. Pyroglutamic Acid

9. Pyrrolidonecarboxylic Acid

2.3.2 Depositor-Supplied Synonyms

1. 98-79-3

2. Pidolic Acid

3. Pyroglutamic Acid

4. 5-oxoproline

5. 5-oxo-l-proline

6. Pyroglutamate

7. H-pyr-oh

8. (2s)-5-oxopyrrolidine-2-carboxylic Acid

9. (s)-5-oxopyrrolidine-2-carboxylic Acid

10. Pyroglu

11. Glutimic Acid

12. L-proline, 5-oxo-

13. (s)-(-)-2-pyrrolidone-5-carboxylic Acid

14. 5-l-oxoproline

15. L-5-oxoproline

16. Pyrrolidonecarboxylic Acid

17. Pidolidone

18. Proline, 5-oxo-

19. (-)-2-pyrrolidone-5-carboxylic Acid

20. Ajidew A-100

21. (s)-pyroglutamic Acid

22. 5-carboxy-2-pyrrolidinone

23. Oxoproline

24. Pidolate

25. L-pyroglutamate

26. 2-pyrrolidinone-5-carboxylic Acid

27. L-5-carboxy-2-pyrrolidinone

28. L-glutiminic Acid

29. L-5-oxo-2-pyrrolidinecarboxylic Acid

30. (s)-5-oxo-2-pyrrolidinecarboxylic Acid

31. 5-pyrrolidinone-2-carboxylic Acid

32. 2-l-pyrrolidone-5-carboxylic Acid

33. Pyroglutamic Acid, L-

34. 5-pyrrolidone-2-carboxylic Acid

35. L-2-pyrrolidone-5-carboxylic Acid

36. L-5-pyrrolidone-2-carboxylic Acid

37. L-pca

38. L-pyrrolidone Carboxylic Acid

39. Nsc 143034

40. (5s)-2-oxopyrrolidine-5-carboxylic Acid

41. Nsc-760414

42. Szb83o1w42

43. Chebi:18183

44. Nsc9966

45. Pyr-oh

46. (s)-2-pyrrolidone-5-carboxylic Acid

47. Nsc-143034

48. 5-oxo-2-pyrrolidinecarboxylic Acid

49. Ncgc00160613-01

50. Dsstox_cid_26260

51. Dsstox_rid_81487

52. Dsstox_gsid_46260

53. Glutiminic Acid

54. Pidolic Acid [inn]

55. L-glutimic Acid

56. Acide Pidolique

57. Oxo-proline

58. Acido Pidolico

59. Acidum Pidolicum

60. Cas-98-79-3

61. 2-pyrrolidone-5-carboxylate

62. L-glutamic Acid Gamma-lactam

63. Pglu-oh

64. Smr000857158

65. Acide Pidolique [inn-french]

66. Acido Pidolico [inn-spanish]

67. Acidum Pidolicum [inn-latin]

68. Pyrrolidinonecarboxylic Acid

69. L-pyrrolidonecarboxylic Acid

70. 2-oxopyrrolidine-5-carboxylic Acid

71. Nsc 9966

72. Einecs 202-700-3

73. L-pyrrolidinonecarboxylic Acid

74. Pyrrolidone-5-carboxylic Acid

75. Proline, 5-oxo-, L-

76. Pidolic Acid [inn:ban]

77. 2-benzothiazolesulfenic Acid Morpholide

78. Unii-szb83o1w42

79. Glutiminate

80. Glutimate

81. Pidolic-acid

82. Pglu

83. L-glutiminate

84. L-glutimate

85. (s)-pyroglutamate

86. (-)-pyroglutamate

87. Mfcd00005272

88. L-pyro-glutamic Acid

89. Pyrrolidinonecarboxylate

90. (l)-pyroglutamic Acid

91. Ajidew A 100

92. L-pyrrolidonecarboxylate

93. Oxopyrrolidinecarboxylate

94. (-)-pyroglutamic Acid

95. L-glutamic Acid Lactam

96. L-pyrrolidinonecarboxylate

97. Pyrrolidone-5-carboxylate

98. L-glutamic Acid G-lactam

99. Pca [inci]

100. Rec-pga 273k

101. Pyrrolidone Car-boxylic Acid

102. L-pyroglutamic Acid, 97%

103. Oxopyrrolidinecarboxylic Acid

104. Schembl15790

105. (s)-(-)-pyroglutamic Acid

106. L-pyroglutamic Acid, Bioxtra

107. Mls001332421

108. Mls001332422

109. 2-pyrrolidinone-5-carboxylate

110. 5-pyrrolidinone-2-carboxylate

111. 2-l-pyrrolidone-5-carboxylate

112. L-2-pyrrolidone-5-carboxylate

113. Pidolic Acid [who-dd]

114. Chembl397976

115. L-glutamic Acid .gamma.-lactam

116. Pyroglutamic Acid, (l)

117. Dtxsid6046260

118. L-pyroglutamic Acid [mi]

119. (s)-2-pyrrolidone-5-carboxylate

120. L-5-oxo-2-pyrrolidinecarboxylate

121. (-)-2-pyrrolidone-5-carboxylate

122. Hms2231l11

123. Hms3264e20

124. Pharmakon1600-01506185

125. 2-oxopyrrolidine-5(s)-carboxylate

126. Pyroglutamic Acid [usp-rs]

127. Act09037

128. Cs-m0659

129. Glp

130. Nsc-9966

131. Nsc11742

132. Str02331

133. Zinc3598263

134. (s)-5-oxo-2-pyrrolidinecarboxylate

135. Tox21_111936

136. Ccg-36432

137. Geo-04256

138. Nsc-11742

139. Nsc760414

140. S5823

141. (5s)-2-oxopyrrolidine-5-carboxylate

142. Akos015855330

143. Tox21_111936_1

144. (2s)-5-pyrrolidone-2-carboxylic Acid

145. (s)-(-)-g-butyrolactam-g-carboxylate

146. (s)-5-oxopyrolidine-2-carboxylic Acid

147. 2-oxopyrrolidine-5(s)-carboxylic Acid

148. Am83732

149. Db03088

150. (s)-(-)-2-pyrrolidone-5-carboxylate

151. L-pyroglutamic Acid, >=99.0% (t)

152. (5s)-2-xopyrrolidine-5-carboxylic Acid

153. Ncgc00160613-02

154. (s)-5-oxo-pyrrolidine-2-carboxylic Acid

155. Ac-15173

156. Bp-12844

157. Hy-76082

158. (s)-(-)-g-butyrolactam-g-carboxylic Acid

159. Db-002779

160. (s)-(-)-2-pyrrolidinone-5-carboxylic Acid

161. P0573

162. (s)-(-)-gamma-butyrolactam-gamma-carboxylate

163. C01879

164. M03204

165. P-8490

166. P17107

167. Ab00514366_07

168. (s)-(-)-gamma-butyrolactam-gamma-carboxylic Acid

169. 005p272

170. A845910

171. Q60998677

172. F8889-8712

173. Z1259273294

174. Pidolic Acid, European Pharmacopoeia (ep) Reference Standard

175. E478f48d-e369-43ae-8132-08d819242518

176. Pyroglutamic Acid, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₅H₇NO₃
Molecular Weight	129.11 g/mol
XLogP3	-0.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	129.042593085 g/mol
Monoisotopic Mass	129.042593085 g/mol
Topological Polar Surface Area	66.4 Å²
Heavy Atom Count	9
Formal Charge	0
Complexity	154
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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

There is currently no clinically approved and/or marketed medicine that relies upon pidolic acid as an active ingredient for any formal therapeutic indication. Although pidolic acid may be sold in a variety of non-prescription, over-the-counter dietary supplement products for cognitive or memory enhancement, there are many studies that suggest that such products or such supplementation do not elicit any kind of cognitive benefit to users. In fact, the general suggestion for any such pidolic acid product is to exercise caution in their recommendation as much more research is necessary. Pidolic acid and sodium pidolic acid are, however, used to some extent in skin and hair conditioning agents owing to their humectant characteristics.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Pidolic acid is a naturally occurring but little-studied amino acid derivative that can be formed enzymatically or non-enzymatically and participates as a biological intermediate in various chemical pathways. Elevations of the acid in blood levels may be associated with problems of glutamine or glutathione metabolism. Pidolic acid, in general, is found in large quantities in brain tissue and other tissues in bound form, like skin. Moreover, pidolic acid in high enough levels can act as an acidogen capable of inducing acidosis and a metabotoxin that can result in adverse health effects. Chronically elevated levels of pidolic acid are associated with at least five inborn errors of metabolism including 5-oxoprolinuria (where 5-oxoproline is otherwise known as pidolic acid), 5-oxoprolinase deficiency, glutathione synthetase deficiency, hawkinsinuria, and propionic acidemia. In particular, abnormally high levels of organic acids like pidolic acid in the blood, urine, brain, and/or other tissues results in general metabolic acidosis. Such acidosis generally occurs when arterial pH falls below 7.35. In infants, the initial symptoms of acidosis consist of poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy. Eventually, acidosis and the symptoms of acidosis can lead to heart, liver, and kidney abnormalities, seizures, coma, and possibly even death. Many children who are afflicted with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. High levels of pidolic acid in the blood have also been demonstrated following acetaminophen overdose, causing an increased level of acidity called a high anion gap metabolic acidosis.

5.2 Absorption, Distribution and Excretion

Absorption

In skin conditioning agents, it has been observed that the percutaneous absorption of 5, 10, and 20% sodium pidolic acid through human skin was 5.97, 6.78, and 5.89%, respectively.

Route of Elimination

In the dog animal model, it was determined that 30% of an absorbed oral administration of pidolic acid was excreted unchanged in the urine and the remainder converted to urea.

Volume of Distribution

Readily available data regarding the volume of distribution of pidolic acid is not available.

Clearance

Readily available data regarding the clearance of pidolic acid is not available.

5.3 Metabolism/Metabolites

In living cells, various metabolic pathways involving pidolic acid exist: (a) glutamyl/glutaminyl (amino acid) n is converted to pyroglutamyl- (amino acid) n by glutaminyl cyclase, pyroglutamyl- (amino acid) n is then metabolised to pyroglutamic acid (pidolic acid) by pyroglutamyl peptidase; (b) via the gamma-Glutamyl cycle, gamma-Glutamyl transpeptidase generates gamma-Glutamyl amino acid which is metabolised to pyroglutamic acid via gamma-Glutamyl cyclotransferase; (c) glutamate via gamma-Glutamylcysteine synthetase or Glutamine synthetase or Glutamate 5-kinase metabolism generates gamma-Glutamyl phosphate which itself can be converted to pyroglutamic acid; and (d) glutamate or glutamine can be non-enzymatically converted to pyroglutamic acid. Finally, pyroglutamic acid (or pidolic acid) itself is metabolized to glutamate via the 5-Oxoprolinase enzyme.

5.4 Biological Half-Life

Some studies have determined that the specific half-life of the N-terminal glutamic acid is about 9 months in a pH 4.1 buffer at 45 degrees Celsius.

5.5 Mechanism of Action

Pidolic acid is an endogenous amino acid derivative where the free amino group of glutamic acid or glutamine cyclizes to generate a lactam. Subsequently it is also a metabolite in the glutathione cycle that is converted to glutamate by the enzyme 5-oxoprolinase. Moreover, N-terminal glutamic acid and glutamine residues can either spontaneously cyclize to become pidolic acid, or be enzymatically transformed by glutaminyl cyclases. In particular, this is ultimately a form of N-termini that is a challenge for N-terminal sequencing using Edman chemistry, which necessitates a free primary amino group that is not present in pidolic acid. Pyroglutamate aminopeptidase can restore a free N-terminus by cleaving off the pyroglutamate residue, however. Additionally, pidolic acid and certain pidolic acid salts like calcium, magnesium, and potassium pidolic acid are sometimes used as skin or hair conditioning agents because of their humectant effects. In such humectant formulations, hydrophilic amine, hydroxyl, or even carboxyl groups possess high affinities for forming hydrogen bonds with molecules of water, allowing the hygroscopic formulations to attract and retain moisture in the air nearby through absorption, therefore drawing the water vapor into the formulation.

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