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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
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
| Molecular Weight | 129.11 g/mol |
|---|---|
| Molecular Formula | C5H7NO3 |
| 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 Ų |
| 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 |
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.
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.
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.
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.
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.
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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