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Details

Stereochemistry ABSOLUTE
Molecular Formula C5H7NO3
Molecular Weight 129.114
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIDOLIC ACID

SMILES

OC(=O)[C@@H]1CCC(=O)N1

InChI

InChIKey=ODHCTXKNWHHXJC-VKHMYHEASA-N
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

HIDE SMILES / InChI
Molecular Formula C5H7NO3
Molecular Weight 129.114
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://www.cir-safety.org/sites/default/files/pca.pdf

Pidolic acid (pyroglutamic acid) is natural amino acid derivative in which the the free amino group of glutamic acid cyclizes to form a lactam. Sodium salt of pyroglutamic acid is used in cosmetics as a moisturizer for dry skin.

CNS Activity

CNS Penetrant
2523
Curator's Comment: Known to penetrate blood-brain barrier in rats. Is produced naturally in human brain

Originator

Haitinger, L.
5
Sources: Haitinger, L.

Approval Year

2002
121
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1410
Collagen alpha-1(I) chain
11
Target ID: P02452|||Q15176|||Q9UML6
Gene ID: 1277.0
Gene Symbol: COL1A1
Target Organism: Homo sapiens (Human)
Activator
1410
Activator
1410
Inhibitor
8228
Inhibitor
8228
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8360
CLEANSING FOAMING GEL ACNE PRO SKIN- zinc pidolate gel

Approved Use

Lange Gel will turn into foam, during application. It will cleanse skin thoroughly without any dryness effect, in order to avoid hyperseboohea phenomenon, a main cause of acne.

Launch Date

1.34256958E12
Primary
Phase I
424
Unknown

Approved Use

Unknown
Primary
Approved
8360
EcoCare™ Zinclean

Approved Use

Use in anti-dandruff shampoos
Primary
Approved
8360
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Human seminal relaxin is a product of the same gene as human luteal relaxin.
1992 May
Characterizing degradation products of peptides containing N-terminal Cys residues by (off-line high-performance liquid chromatography)/matrix-assisted laser desorption/ionization quadrupole time-of-flight measurements.
2003
Determination of the post-translational modifications of salivary acidic proline-rich proteins.
2003 Apr
Beta-lactams as versatile synthons for homochiral ibotenate analogues with potential for activity at glutamate receptors.
2003 Aug 7
Pressure/temperature combined treatments of precursors yield hormone-like peptides with pyroglutamate at the N terminus.
2003 Dec 31
[Evolution of the neuroprotection concept].
2003 Mar-Apr
[Oleyl pyroglutamate for use as transdermal enhancer and its enhancing mechanism].
2003 May
Origin of diastereoselection in the hydrosilylation of chiral N-acyliminium intermediates derived from pyroglutamic acid.
2004 Apr 26
Glutaminyl cyclases unfold glutamyl cyclase activity under mild acid conditions.
2004 Apr 9
Glutamine in commercial liquid nutritional products.
2004 Aug 11
Toward the synthesis of pyroglutamate lauroyl ester: biocatalysis versus chemical catalysis.
2004 Feb
Stabilization of peptide guinea pig myelin basic protein 72-85 by N-terminal acetylation-implications for immunological studies.
2004 Feb
Expression, purification, and characterization of avian Thy-1 from Lec1 mammalian and Tn5 insect cells.
2004 Feb
Identification of endogenous phosphorylation sites of bovine medium and low molecular weight neurofilament proteins by tandem mass spectrometry.
2004 Feb 24
N-acetylation of the glutamate residue of intact glutathione conjugates in rats: a novel pathway for the metabolic processing of thiol adducts of xenobiotics.
2004 Jan
Integrative annotation of 21,037 human genes validated by full-length cDNA clones.
2004 Jun
Chemical characterization of a lambda I amyloid protein isolated from formalin-fixed and paraffin-embedded tissue sections.
2004 Mar
Unexplained metabolic acidosis in critically ill patients: the role of pyroglutamic acid.
2004 Mar
Skin secretion of the toad Bombina variegata contains multiple insulin-releasing peptides including bombesin and entirely novel insulinotropic structures.
2004 Mar-Apr
Mass spectrometric analysis of posttranslational modifications of a carrot extracellular glycoprotein.
2004 May 25
Preventing the spontaneous modification of an HLA-A2-restricted peptide at an N-terminal glutamine or an internal cysteine residue enhances peptide antigenicity.
2004 May-Jun
Discrepin, a new peptide of the sub-family alpha-ktx15, isolated from the scorpion Tityus discrepans irreversibly blocks K+ -channels (IA currents) of cerebellum granular cells.
2004 Oct 15
Alpha-tocopherol pro-vitamins: synthesis, hydrolysis and accumulation in rabbit ear skin.
2004 Oct 19
Isolation of an anti-angiogenic substance from Agaricus blazei Murill: its antitumor and antimetastatic actions.
2004 Sep
Obligatory involvement of CD26/dipeptidyl peptidase IV in the activation of the antiretroviral tripeptide glycylprolylglycinamide (GPG-NH(2)).
2004 Sep
The development of a higher throughput reactive intermediate screening assay incorporating micro-bore liquid chromatography-micro-electrospray ionization-tandem mass spectrometry and glutathione ethyl ester as an in vitro conjugating agent.
2004 Sep 21
Mass spectrometry analysis of recombinant human ZP3 expressed in glycosylation-deficient CHO cells.
2004 Sep 28
A high-throughput liquid chromatography/tandem mass spectrometry method for screening glutathione conjugates using exact mass neutral loss acquisition.
2005
The computer modelling of human TRH receptor, TRH and TRH-like peptides.
2005
Anuroctoxin, a new scorpion toxin of the alpha-KTx 6 subfamily, is highly selective for Kv1.3 over IKCa1 ion channels of human T lymphocytes.
2005 Apr
Emerging roles of apelin in biology and medicine.
2005 Aug
Nanoparticles on the basis of highly functionalized dextrans.
2005 Aug 3
Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.
2005 Aug 7
Physiological and pathological aspects of GSH metabolism.
2005 Feb
Acetaminophen-induced anion gap metabolic acidosis and 5-oxoprolinuria (pyroglutamic aciduria) acquired in hospital.
2005 Jul
Recurrent high anion gap metabolic acidosis secondary to 5-oxoproline (pyroglutamic acid).
2005 Jul
Identification of novel bradykinin-potentiating peptides and C-type natriuretic peptide from Lachesis muta venom.
2005 Jul
The removal of pyroglutamic acid from monoclonal antibodies without denaturation of the protein chains.
2005 Jul 1
CLPM: a cross-linked peptide mapping algorithm for mass spectrometric analysis.
2005 Jul 15
Total synthesis of pinnamine and anatoxin-a via a common intermediate. A caveat on the anatoxin-a endgame.
2005 Jul 8
Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids.
2005 Mar
Bromophenols coupled with derivatives of amino acids and nucleosides from the red alga Rhodomela confervoides.
2005 May
Biomarker metabolites capturing the metabolite variance present in a rice plant developmental period.
2005 May 31
Familial Danish dementia: co-existence of Danish and Alzheimer amyloid subunits (ADan AND A{beta}) in the absence of compact plaques.
2005 Nov 4
Cloning, expression, characterization, and crystallization of a glutaminyl cyclase from human bone marrow: a single zinc metalloenzyme.
2005 Sep
Synthesis of 1,3-dioxo-hexahydropyrido[1,2-c][1,3]diazepine carboxylates, a new bicyclic skeleton formed by ring expansion-RCM methodology.
2005 Sep 21
Thermostability and in vitro digestibility of a purified major allergen 2S albumin (Ses i 1) from white sesame seeds (Sesamum indicum L.).
2005 Sep 25
CFSUM1 and CFSUM2 in urine from patients with chronic fatigue syndrome are methodological artefacts.
2006 Feb
Zinc l-pyrrolidone carboxylate inhibits the UVA-induced production of matrix metalloproteinase-1 by in vitro cultured skin fibroblasts, whereas it enhances their collagen synthesis.
2012 Feb
Comparative effect of a new mouthrinse containing chlorhexidine, triclosan and zinc on volatile sulphur compounds: a randomized, crossover, double-blind study.
2016 Aug
Patents

Patents

04762851
5
04847250
5
04940816
6
04952706
5
05411989
5
06310095
9
08791102
6
US20050163737
5
US7326409
5

Sample Use Guides

In Vivo Use Guide
Lange Gel will turn into foam, during application. It will cleanse skin thoroughly without any dryness effect, in order to avoid hyperseboohea phenomenon, a main cause of acne.
Route of Administration: Topical
In Vitro Use Guide
When normal human dermal fibroblasts were irradiated with UVA after a pre-treatment with 10 uM of Zinc Pidolate (Zinc PCA) for 16 h, this pretreatment suppressed the UVA-induced c-Fos expression to 110%, in comparison with the value of 200% obtained without such Zinc PCA pre-treatment. Zinc PCA induced SVCT2 mRNA expression in NHDFs in a dose-dependent manner, i.e., 115% at 25 uM and 125% at 50 uM, in comparison with the control.
Substance Class Chemical
Created
by admin
on Thu Jul 06 21:59:22 UTC 2023
Edited
by admin
on Thu Jul 06 21:59:22 UTC 2023
Record UNII
SZB83O1W42
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIDOLIC ACID
INN   WHO-DD  
INN  
Official Name English
GLP
Common Name English
L-PYROGLUTAMIC ACID
MI  
Common Name English
PYROGLUTAMIC ACID
Common Name English
5-OXO-L-PROLINE
Systematic Name English
AJIDEW A-100
Brand Name English
PCA
INCI  
INCI  
Official Name English
Pidolic acid [WHO-DD]
Common Name English
PYROGLUTAMIC ACID, L-
Common Name English
L-PYRROLIDONE CARBOXYLIC ACID
Common Name English
5-L-OXOPROLINE
Common Name English
5-OXOPROLINE
Common Name English
L-PCA
Common Name English
PYROGLUTAMATE
Common Name English
PYROGLU
Common Name English
pidolic acid [INN]
Common Name English
PIDOLIDONE
Brand Name English
L-PYROGLUTAMIC ACID [MI]
Common Name English
5-OXO-2-PYRROLIDINECARBOXYLIC ACID
Systematic Name English
(-)-2-PYRROLIDONE-5-CARBOXYLIC ACID
Systematic Name English
PYROGLUTAMIC ACID [USP-RS]
Common Name English
GLUTIMIC ACID
Common Name English
PCA [INCI]
Common Name English
NSC-143034
Code English
NSC-760414
Code English
Classification Tree Code System Code
LOINC 75089-3
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
LOINC 13700-0
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
DSLD 2731 (Number of products:44)
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
NCI_THESAURUS C29703
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
LOINC 29872-9
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
LOINC 29522-0
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
LOINC 53394-3
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
LOINC 53232-5
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
LOINC 43633-7
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
EU-Orphan Drug EU/3/16/1673
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
Code System Code Type Description
NSC
760414
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID6046260
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
NSC
143034
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
CHEBI
16010
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
RXCUI
155060
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
PYROGLUTAMIC ACID
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
CHEBI
58402
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
RS_ITEM_NUM
1589029
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
CHEBI
18183
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
MERCK INDEX
M9383
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY Merck Index
INN
4079
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
CAS
98-79-3
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
CHEBI
30652
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
DAILYMED
SZB83O1W42
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
PUBCHEM
7405
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
DRUG BANK
DB03088
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
SMS_ID
100000081944
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
ECHA (EC/EINECS)
202-700-3
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
EVMPD
SUB09825MIG
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
CHEBI
57606
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
NCI_THESAURUS
C82933
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
FDA UNII
SZB83O1W42
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL284718
Created by admin on Thu Jul 06 21:59:24 UTC 2023 , Edited by admin on Thu Jul 06 21:59:24 UTC 2023
PRIMARY
Related Record Type Details
Structure of ZINC PIDOLATE
SALT/SOLVATE -> PARENT
Structure of POTASSIUM PIDOLATE
SALT/SOLVATE -> PARENT
Structure of MANGANESE PIDOLATE
SALT/SOLVATE -> PARENT
Structure of ARGININE PIDOLATE
SALT/SOLVATE -> PARENT
Structure of CALCIUM PIDOLATE
SALT/SOLVATE -> PARENT
Structure of COPPER PIDOLATE
SALT/SOLVATE -> PARENT
Structure of METADOXINE
SALT/SOLVATE -> PARENT
Structure of TROLAMINE PIDOLATE
SALT/SOLVATE -> PARENT
Structure of MAGNESIUM ASCORBATE/PIDOLATE
SALT/SOLVATE -> PARENT
Structure of SODIUM PIDOLATE
SALT/SOLVATE -> PARENT
Structure of PROCAINE PIDOLATE
SALT/SOLVATE -> PARENT
Structure of MAGNESIUM PIDOLATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of PIDOLIC ACID
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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