PIDOLIC ACID

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C5H7NO3
Molecular Weight	129.1142
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1CC(=N[C@]1([H])C(=O)O)O

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	129.1142
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://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.htmhttp://www.currentscience.ac.in/Volumes/102/02/0288.pdf
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

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 1343
Collagen alpha-1(I) chain 9 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 1343
Transcription factor AP1 5 Target ID: CHEMBL2111421 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21834944	Activator 1343
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 7728
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 7728

Conditions

Condition	Modality	Highest Phase	Product
Acne 96 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 8043	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
Halitosis 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25727335	Primary	Phase I 409	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 8043	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 8043	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
Fast analysis of water samples for detection of anions by capillary zone electrophoresis.	2001	11545352
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
Stability and CTL activity of N-terminal glutamic acid containing peptides.	2001 Jun	11437956
Characterization of cigar tobaccos by gas chromatographic/mass spectrometric analysis of nonvolatile organic acids: application to the authentication of Cuban cigars.	2001 Mar	11312824
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
Stability and CTL-activity of P40/ELA melanoma vaccine candidate.	2001 Sep-Dec	11851331
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
Spectrophotometric assays for L-lysine alpha-oxidase and gamma-glutamylamine cyclotransferase.	2002 Apr 15	11950211
CLAC: a novel Alzheimer amyloid plaque component derived from a transmembrane precursor, CLAC-P/collagen type XXV.	2002 Apr 2	11927537
Conformationally restricted TRH analogues: constraining the pyroglutamate region.	2002 Feb	11741778
Production of pyroglutamic acid by thermophilic lactic acid bacteria in hard-cooked mini-cheeses.	2002 Oct	12416800
Refolding of amphioxus insulin-like peptide: implications of a bifurcating evolution of the different folding behavior of insulin and insulin-like growth factor 1.	2003 Aug 19	12911310
Pressure/temperature combined treatments of precursors yield hormone-like peptides with pyroglutamate at the N terminus.	2003 Dec 31	14690402
Isolation and identification of indigestible pyroglutamyl peptides in an enzymatic hydrolysate of wheat gluten prepared on an industrial scale.	2003 Jan 1	12502378
[Neuroprotective properties of pyroglutamic acid in combination with pyrrolidone].	2003 Jan-Feb	12683075
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
[Oleyl pyroglutamate for use as transdermal enhancer and its enhancing mechanism].	2003 May	12958846
Proinsulin C-peptide and its C-terminal pentapeptide: degradation in human serum and Schiff base formation with subsequent CO2 incorporation.	2003 May	12827290
Origin of diastereoselection in the hydrosilylation of chiral N-acyliminium intermediates derived from pyroglutamic acid.	2004 Apr 26	15114576
Glutaminyl cyclases unfold glutamyl cyclase activity under mild acid conditions.	2004 Apr 9	15063747
Glutamine in commercial liquid nutritional products.	2004 Aug 11	15291459
Toward the synthesis of pyroglutamate lauroyl ester: biocatalysis versus chemical catalysis.	2004 Feb	15049361
Human glutaminyl cyclase and bacterial zinc aminopeptidase share a common fold and active site.	2004 Feb 10	15028118
Mass spectrometric analysis of posttranslational modifications of a carrot extracellular glycoprotein.	2004 May 25	15147212
Alpha-tocopherol pro-vitamins: synthesis, hydrolysis and accumulation in rabbit ear skin.	2004 Oct 19	15451598
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	15351054
Mass spectrometry analysis of recombinant human ZP3 expressed in glycosylation-deficient CHO cells.	2004 Sep 28	15379548
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
Acetaminophen-induced anion gap metabolic acidosis and 5-oxoprolinuria (pyroglutamic aciduria) acquired in hospital.	2005 Jul	15983968
Identification of novel bradykinin-potentiating peptides and C-type natriuretic peptide from Lachesis muta venom.	2005 Jul	15876444
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
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

Patents

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 `Fri Jun 25 21:56:40 UTC 2021` Edited by `admin` on `Fri Jun 25 21:56:40 UTC 2021`
Record UNII	SZB83O1W42
Record Status	`Validated (UNII)`
Record Version

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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

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

PIDOLIC ACID [WHO-DD]

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