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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
Structure of PYRROLIDONE CARBOXYLIC ACID

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)

HIDE SMILES / InChI

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 ( + / - )

Description
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

Curator's Comment: Known to be CNS penetrant in rats. Human data not available

Originator

Curator's Comment: Haitinger, L., Vorlauge Mittheilung iiber Glutaminsaure und Pyrrol. Monatsh. Chem., 1882, 3, 228–229.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Hydromol® CREAM

Approved Use

Dry skin conditions including dermatitis, eczema, ichthyosis and senile pruritus.
Palliative
Hydromol® CREAM

Approved Use

Dry skin conditions including dermatitis, eczema, ichthyosis and senile pruritus.
Palliative
Hydromol® CREAM

Approved Use

Dry skin conditions including dermatitis, eczema, ichthyosis and senile pruritus.
PubMed

PubMed

TitleDatePubMed
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

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:57:17 GMT 2023
Edited
by admin
on Fri Dec 15 18:57:17 GMT 2023
Record UNII
6VT1YZM21H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRROLIDONE CARBOXYLIC ACID
Systematic Name English
DL-PYROGLUTAMIC ACID
Common Name English
(±)-2-PYRROLIDONE-5-CARBOXYLIC ACID
Systematic Name English
PIDOLIC ACID, DL-
Common Name English
DL-2-PYRROLIDONE-5-CARBOXYLIC ACID
Common Name English
DL-PYRROLIDONECARBOXYLIC ACID
Common Name English
DL-2-PYRROLIDINONE-5-CARBOXYLIC ACID
Common Name English
5-OXO-DL-PROLINE
Systematic Name English
PROLINE, 5-OXO-, DL-
Systematic Name English
NSC-40887
Code English
PYROGLUTAMIC ACID, DL-
Common Name English
(±)-PYROGLUTAMIC ACID
Common Name English
DL-PROLINE, 5-OXO-
Systematic Name English
Code System Code Type Description
CAS
149-87-1
Created by admin on Fri Dec 15 18:57:17 GMT 2023 , Edited by admin on Fri Dec 15 18:57:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-748-3
Created by admin on Fri Dec 15 18:57:17 GMT 2023 , Edited by admin on Fri Dec 15 18:57:17 GMT 2023
PRIMARY
CHEBI
16010
Created by admin on Fri Dec 15 18:57:17 GMT 2023 , Edited by admin on Fri Dec 15 18:57:17 GMT 2023
PRIMARY
RXCUI
9036
Created by admin on Fri Dec 15 18:57:17 GMT 2023 , Edited by admin on Fri Dec 15 18:57:17 GMT 2023
PRIMARY
DRUG BANK
DB11245
Created by admin on Fri Dec 15 18:57:17 GMT 2023 , Edited by admin on Fri Dec 15 18:57:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID80859174
Created by admin on Fri Dec 15 18:57:17 GMT 2023 , Edited by admin on Fri Dec 15 18:57:17 GMT 2023
PRIMARY
FDA UNII
6VT1YZM21H
Created by admin on Fri Dec 15 18:57:17 GMT 2023 , Edited by admin on Fri Dec 15 18:57:17 GMT 2023
PRIMARY
PUBCHEM
499
Created by admin on Fri Dec 15 18:57:17 GMT 2023 , Edited by admin on Fri Dec 15 18:57:17 GMT 2023
PRIMARY
DAILYMED
6VT1YZM21H
Created by admin on Fri Dec 15 18:57:17 GMT 2023 , Edited by admin on Fri Dec 15 18:57:17 GMT 2023
PRIMARY
NSC
40887
Created by admin on Fri Dec 15 18:57:17 GMT 2023 , Edited by admin on Fri Dec 15 18:57:17 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY