PIDOLIC ACID

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 Search

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

Description
Sources: http://www.currentscience.ac.in/Volumes/102/02/0288.pdfhttps://www.drugs.com/otc/121041/cleansing-foaming-gel-acne-pro-skin.html | https://www.ncbi.nlm.nih.gov/pubmed/25727335 | https://www.ncbi.nlm.nih.gov/pubmed/21834944 | https://www.ulprospector.com/en/na/PersonalCare/Detail/6637/223524/EcoCare-Zinclean | http://www.scalp-health.com/zinc-pca.htm
Curator's Comment: description was created based on several sources, including http://www.cir-safety.org/sites/default/files/pca.pdf

Zinc Pidolate (Zinc PCA) is a topical skin product with purifying, astingent, anti-inflammatory, antiseptic activity. It has long been used as a cosmetic ingredient, because of its astringent and anti-microbial properties. Zinc Pidolate has also being shown to be effective against halitosis. Zinc PCA prevents the UV-induced MMP-1 production in vitro by suppressing the activation of AP-1. Zinc PCA was also able to enhance type I collagen synthesis in NHDFs, by increasing the expression of the mRNA encoding the ascorbic acid transporter SVCT2 in non-UV irradiated NHDFs, which suggests its promising effect against not only photoaged skin but also for the simple atrophic change of intrinsic skin ageing. Zinc PCA is able to suppress sebum secretion by inhibiting 5-α reductase in hyperseborrhea, to suppress body odor by forming zinc salts with short-chain fatty acids, to suppress wrinkles by inhibiting AP-1 to and inhibit bacterial growth including acne related Propionibacterium acnes.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium-dependent vitamin C transporter 2 5 Target ID: CHEMBL3271 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21834944	Activator 1430
Collagen alpha-1(I) chain 11 Target ID: P02452\|\|\|Q15176\|\|\|Q9UML6 Gene ID: 1277.0 Gene Symbol: COL1A1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21834944	Activator 1430
Transcription factor AP1 6 Target ID: CHEMBL2111421 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21834944	Activator 1430
Propionibacterium acnes 6 Target ID: CHEMBL612639 Sources: http://www.in-cosmetics.com/__novadocuments/4317 \| https://www.ulprospector.com/en/na/PersonalCare/Detail/6637/223524/EcoCare-Zinclean	Inhibitor 8297
Steroid 5-alpha-reductase 15 Target ID: CHEMBL2363075 Sources: https://www.ulprospector.com/en/na/PersonalCare/Detail/6637/223524/EcoCare-Zinclean \| www.google.com/patents/US20090203628 \| http://www.in-cosmetics.com/__novadocuments/4317	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Acne 98 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=cab1d71c-e017-4ff3-853b-b0e47dc1ee79&type=display http://www.solabia.com/Produto_7,1/Cosmetics/Zincidone.html http://www.scalp-health.com/zinc-pca.htm	Preventing	Approved 8429	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 2012
Halitosis 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25727335	Primary	Phase I 428	Unknown Approved Use Unknown
Seborrhea 11 Sources: http://www.in-cosmetics.com/__novadocuments/4317 http://www.scalp-health.com/zinc-pca.htm http://www.solabia.com/Produto_7,1/Cosmetics/Zincidone.html http://cosmetics.specialchem.com/product/i-ecochem-ecocare-zinclean	Primary	Approved 8429	EcoCare™ Zinclean Approved Use Use in anti-dandruff shampoos
Dry skin 6 Sources: http://www.cir-safety.org/sites/default/files/pca.pdf	Primary	Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Human seminal relaxin is a product of the same gene as human luteal relaxin.	1992 May	1572287
Strain-based sequence variations and structure analysis of murine prostate specific spermine binding protein using mass spectrometry.	2001 Aug 14	11583173
Chromosome 13 dementia syndromes as models of neurodegeneration.	2001 Dec	11791622
Recombinant wheat antifungal PR4 proteins expressed in Escherichia coli.	2001 Dec	11722174
Electrophilic fluorination of pyroglutamic acid derivatives: application of substrate-dependent reactivity and diastereoselectivity to the synthesis of optically active 4-fluoroglutamic acids.	2001 Dec 28	11749613
A simultaneous assay method for L-glutamate and L-pyroglutamate contents in soy sauce using a 5-oxoprolinase (without ATP hydrolyzing activity).	2001 Feb	11302195
Inhibition of a model protease--pyroglutamate aminopeptidase by a natural oligosaccharide gum from Hakea gibbosa.	2001 Jan 16	11165074
Massive 5-oxoprolinuria with normal 5-oxoprolinase and glutathione synthetase activities.	2001 Jun	11486906
Stability and CTL activity of N-terminal glutamic acid containing peptides.	2001 Jun	11437956
In vivo confocal Raman microspectroscopy of the skin: noninvasive determination of molecular concentration profiles.	2001 Mar	11231318
The mechanism of aubstrate eecognition of pyroglutamyl-peptidase I from Bacillus amyloliquefaciens as determined by X-ray crystallography and site-directed mutagenesis.	2001 May 25	11359794
Expression and prognostic significance of lysozyme in male breast cancer.	2002	12473177
Comparison of the positive and negative ion electrospray mass spectra of some small peptides containing pyroglutamate.	2002	11816043
Complete structure of an increasing capillary permeability protein (ICPP) purified from Vipera lebetina venom. ICPP is angiogenic via vascular endothelial growth factor receptor signalling.	2002 Aug 16	12021274
Stereoselective total syntheses of the racemic form and the natural enantiomer of the marine alkaloid lepadiformine via a novel N-acyliminium ion/allylsilane spirocyclization strategy.	2002 Jun 14	12054972
Two novel antifungal peptides distinct with a five-disulfide motif from the bark of Eucommia ulmoides Oliv.	2002 Jun 19	12067732
Pseudopeptide foldamers: the homo-oligomers of pyroglutamic acid.	2002 Jun 3	12180330
Determination of the post-translational modifications of salivary acidic proline-rich proteins.	2003 Apr	15621862
Pigment-epithelium-derived factor (PEDF) occurs at a physiologically relevant concentration in human blood: purification and characterization.	2003 Aug 15	12737624
Solution structure of the cytotoxic RNase 4 from oocytes of bullfrog Rana catesbeiana.	2003 Feb 28	12589762
Characterization of a new bradykinin-potentiating peptide (TmF) from Trimeresurus mucrosquamatus.	2003 Jul	12883631
Reinvestigation of the proposed folding and self-association of the Neuropeptide Head Activator.	2003 Mar	12592026
[Characteristics of pyrrolidone pharmacokinetics in rats].	2003 Nov-Dec	14743713
Human glutaminyl cyclase and bacterial zinc aminopeptidase share a common fold and active site.	2004 Feb 10	15028118
Chemical characterization of a lambda I amyloid protein isolated from formalin-fixed and paraffin-embedded tissue sections.	2004 Mar	15185499
Synthesis of (2S,3S)-3'-fluoroisoleucine.	2004 Mar 7	14985821
Obligatory involvement of CD26/dipeptidyl peptidase IV in the activation of the antiretroviral tripeptide glycylprolylglycinamide (GPG-NH(2)).	2004 Sep	15183349
A high-throughput liquid chromatography/tandem mass spectrometry method for screening glutathione conjugates using exact mass neutral loss acquisition.	2005	15714601
Emerging roles of apelin in biology and medicine.	2005 Aug	15907343
Formation of extracellular glutamate from glutamine: exclusion of pyroglutamate as an intermediate.	2005 Aug 2	16004974
Nanoparticles on the basis of highly functionalized dextrans.	2005 Aug 3	16045324
Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.	2005 Aug 7	16032366
Physiological and pathological aspects of GSH metabolism.	2005 Feb	15981742
Acetaminophen-induced anion gap metabolic acidosis and 5-oxoprolinuria (pyroglutamic aciduria) acquired in hospital.	2005 Jul	15983968
Recurrent high anion gap metabolic acidosis secondary to 5-oxoproline (pyroglutamic acid).	2005 Jul	15983950
Identification of novel bradykinin-potentiating peptides and C-type natriuretic peptide from Lachesis muta venom.	2005 Jul	15876444
The removal of pyroglutamic acid from monoclonal antibodies without denaturation of the protein chains.	2005 Jul 1	15958188
CLPM: a cross-linked peptide mapping algorithm for mass spectrometric analysis.	2005 Jul 15	16026606
Total synthesis of pinnamine and anatoxin-a via a common intermediate. A caveat on the anatoxin-a endgame.	2005 Jul 8	15989354
Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids.	2005 Mar	15635648
Bromophenols coupled with derivatives of amino acids and nucleosides from the red alga Rhodomela confervoides.	2005 May	15921411
Biomarker metabolites capturing the metabolite variance present in a rice plant developmental period.	2005 May 31	15927065
Familial Danish dementia: co-existence of Danish and Alzheimer amyloid subunits (ADan AND A{beta}) in the absence of compact plaques.	2005 Nov 4	16091362
Cloning, expression, characterization, and crystallization of a glutaminyl cyclase from human bone marrow: a single zinc metalloenzyme.	2005 Sep	16084398
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	16136256
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	16140598
CFSUM1 and CFSUM2 in urine from patients with chronic fatigue syndrome are methodological artefacts.	2006 Feb	16095585
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	21834944
Comparative effect of a new mouthrinse containing chlorhexidine, triclosan and zinc on volatile sulphur compounds: a randomized, crossover, double-blind study.	2016 Aug	25727335

Patents

Sample Use Guides

In Vivo Use Guide

Topical, as a compontent of lotions, creams and other cosmetic products.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Name

Type

Language

PIDOLIC ACID

Official Name

English

GLP

Common Name

English

L-PYROGLUTAMIC ACID

Common Name

English

PYROGLUTAMIC ACID

Common Name

English

5-OXO-L-PROLINE

Systematic Name

English

AJIDEW A-100

Brand Name

English

PCA	Locators: INCI Naming Organization: INCI Sources:

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