Details
Stereochemistry | RACEMIC |
Molecular Formula | C5H7NO3 |
Molecular Weight | 129.114 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1CCC(=O)N1
InChI
InChIKey=ODHCTXKNWHHXJC-UHFFFAOYSA-N
InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)
Molecular Formula | C5H7NO3 |
Molecular Weight | 129.114 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.medicines.org.uk/emc/medicine/18948
http://www.centerchem.com/Products/DownloadFile.aspx?FileID=6642
Curator's Comment: description was created based on several sources, including
https://www.medicines.org.uk/emc/medicine/18948
http://www.centerchem.com/Products/DownloadFile.aspx?FileID=6642
Pyroglutamic acid (also known as PCA, 5-oxoproline, pidolic acid, or pyroglutamate for its basic form) exists as two distinct enantiomers: (2R) or D and (2S) or L. L-form is a metabolite in the glutathione cycle that is converted to glutamate by 5-oxoprolinase. L-Pyroglutamic acid is produced in the skin through the arginine-citrulline-ornitine-glutamic pathway. The free acid is not hygroscopic; however, the sodium salts of this acid are more hygroscopic than glycerine. Therefore, formulation of this acid is suggested as a defense against dehydration, for skin conditions involving desquamation. Hydromol Cream (main component of that is sodium pyrrolidone carboxylate (L form)) is a soft cream which moisturises the skin. Hydromol Cream contains a naturally occurring moisturising agent as well as oils, which prevent moisture loss from the skin. This helps to relieve itch, lubricate and soften the skin. Hydromol Cream is used to treat any condition in which dry skin is a feature such as eczema, ichthyosis (hereditary dry skin) and senile pruritus (itching that may occur in old age). L-Pyroglutamic acid is present in living cells has been reported from archaebacteria to humans, and its occurrence in living cells has been known for over a century. Despite its almost ubiquitous presence, the role of pyroglutamic acid in living cells is poorly understood. Pyroglutamic acid is found as an N-terminal modification in many neuronal peptides and hormones that also include the accumulating peptides in Alzheimer’s disease and familial dementia. The modification is also observed in proteins that include many antibodies, some enzymes and structural proteins.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7080082
Curator's Comment: Known to be CNS penetrant in rats. Human data not available
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Hydromol® CREAM Approved UseDry skin conditions including dermatitis, eczema, ichthyosis and senile pruritus. |
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Palliative | Hydromol® CREAM Approved UseDry skin conditions including dermatitis, eczema, ichthyosis and senile pruritus. |
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Palliative | Hydromol® CREAM Approved UseDry skin conditions including dermatitis, eczema, ichthyosis and senile pruritus. |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of the hemoregulatory peptide (pEEDCK)2 (pyroGlu-Glu-Asp-Cys-Lys)2 and MIP-1alpha is reduced in bone marrow cultures from patients with chronic myeloid leukemia (CML). | 2001 |
|
Sequence and expression of the CAPA/CAP2b gene in the tobacco hawkmoth, Manduca sexta. | 2004 Oct |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:57:17 GMT 2023
by
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on
Fri Dec 15 18:57:17 GMT 2023
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Record UNII |
6VT1YZM21H
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |