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Details

Stereochemistry RACEMIC
Molecular Formula C5H6NO3.Na
Molecular Weight 151.0958
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM PYRROLIDONE CARBOXYLATE

SMILES

[Na+].[O-]C(=O)C1CCC(=O)N1

InChI

InChIKey=CRPCXAMJWCDHFM-UHFFFAOYSA-M
InChI=1S/C5H7NO3.Na/c7-4-2-1-3(6-4)5(8)9;/h3H,1-2H2,(H,6,7)(H,8,9);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C5H6NO3
Molecular Weight 128.106
Charge -1
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
Sequence and expression of the CAPA/CAP2b gene in the tobacco hawkmoth, Manduca sexta.
2004 Oct
Structure-activity relationships for in vitro diuretic activity of CAP2b in the housefly.
2007 Jan
A second gene encodes the anti-diuretic hormone in the insect, Rhodnius prolixus.
2010 Apr 12
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 15:49:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:30 GMT 2023
Record UNII
469OTG57A2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM PYRROLIDONE CARBOXYLATE
II   VANDF  
Systematic Name English
SODIUM PYRROLIDONE CARBOXYLATE [VANDF]
Common Name English
DL-SODIUM PIDOLATE
Common Name English
PIDOLATE SODIUM, DL-
Common Name English
DL-PROLINE, 5-OXO-, MONOSODIUM SALT
Common Name English
5-OXO-DL-PROLINE, MONOSODIUM SALT
Common Name English
PCA SODA
Common Name English
SODIUM DL-PYROGLUTAMATE
Common Name English
AJIDEW N-50
Brand Name English
SODIUM PYRROLIDONE CARBOXYLATE [II]
Common Name English
Sodium DL-pyroglutamate [WHO-DD]
Common Name English
SODIUM PCA [INCI]
Common Name English
DL-SODIUM PYROGLUTAMATE
Common Name English
SODIUM DL-PYRROLIDONECARBOXYLATE
Common Name English
PYRROLIDONE CARBOXYLIC ACID, SODIUM SALT
Common Name English
SODIUM PCA
INCI  
INCI  
Official Name English
Code System Code Type Description
EPA CompTox
DTXSID20885432
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
CONCEPT Industrial Aid
PUBCHEM
23666346
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
PRIMARY
DAILYMED
469OTG57A2
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
PRIMARY
FDA UNII
469OTG57A2
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
PRIMARY
NCI_THESAURUS
C84168
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
PRIMARY
RXCUI
1364924
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
PRIMARY RxNorm
CAS
54571-67-4
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
259-234-9
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
PRIMARY
EVMPD
SUB28928
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
PRIMARY
SMS_ID
100000092937
Created by admin on Fri Dec 15 15:49:30 GMT 2023 , Edited by admin on Fri Dec 15 15:49:30 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY