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C7081

WY-14643

Name: WY-14643
Brand: SIGMA

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Synonym(s):

4-Chloro-6-(2,3-xylidino)-2-pyrimidinylthioacetic acid, Pirinixic acid

Empirical Formula (Hill Notation):

C₁₄H₁₄ClN₃O₂S

CAS Number:

50892-23-4

Molecular Weight:

323.80

MDL number:

MFCD00191335

PubChem Substance ID:

24892928

NACRES:

NA.77

form

powder

Quality Level

100

SMILES string

CC1=C(C)C=CC=C1NC2=NC(SCC(O)=O)=NC(Cl)=C2

InChI

1S/C14H14ClN3O2S/c1-8-4-3-5-10(9(8)2)16-12-6-11(15)17-14(18-12)21-7-13(19)20/h3-6H,7H2,1-2H3,(H,19,20)(H,16,17,18)

InChI key

SZRPDCCEHVWOJX-UHFFFAOYSA-N

Gene Information

human ... PPARA(5465) , PPARD(5467) , PPARG(5468)
mouse ... Ppara(19013)
rat ... Ppara(25747)

General description

WY-14643 prevents lipopolysaccharide (LPS)-induced inflammation in synovial fibroblasts. It protects cortical neurons from pro-inflammatory mediator-induced cell injuries. WY-14643 has inhibitory effects on pro-inflammatory responses in microglia. It improves oxido-nitrosative stress in disease models and reduces the generation of reactive oxygen species (ROS), nitric oxide (NO) and lipid peroxidation end-products in the brain.

Application

WY-14643 has been used:

as a positive control for transfection and luciferase assay
to stimulate bone marrow–derived macrophages (BMDM) for autophagic flux analysis
to analyze the regulation of fatty acid metabolism-immune nexus (FAMIN) expression in cell culture

Biochem/physiol Actions

Selective PPARα agonist.

Features and Benefits

This compound is featured on the Nuclear Receptors (Non-Steroids) and Nuclear Receptors (PPARs) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

GHS07,GHS08

Signal Word

Danger

Hazard Statements

H302 - H315 - H319 - H335 - H350

Precautionary Statements

P201 - P301 + P312 + P330 - P302 + P352 - P305 + P351 + P338 - P308 + P313

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Perfluorinated Carboxylic Acids with Increasing Carbon Chain Lengths Upregulate Amino Acid Transporters and Modulate Compensatory Response of Xenobiotic Transporters in HepaRG Cells.

Joe Jongpyo Lim et al.

Drug metabolism and disposition: the biological fate of chemicals, 50(10), 1396-1413 (2021-12-04)

Perfluorinated carboxylic acids (PFCAs) are widespread environmental pollutants for which human exposure has been documented. PFCAs at high doses are known to regulate xenobiotic transporters partly through peroxisome proliferator-activated receptor alpha (PPARα) and constitutive androstane receptor (CAR) in rodent models.

Tumor necrosis factor α stimulates endogenous apolipoprotein A-I expression and secretion by human monocytes and macrophages: role of MAP-kinases, NF-κB, and nuclear receptors PPARα and LXRs.

Vladimir S Shavva et al.

Molecular and cellular biochemistry, 448(1-2), 211-223 (2018-02-15)

Apolipoprotein A-I (ApoA-I) is the main structural and functional protein component of high-density lipoprotein. ApoA-I has been shown to regulate lipid metabolism and inflammation in macrophages. Recently, we found the moderate expression of endogenous apoA-I in human monocytes and macrophages

WY-14643, a selective agonist of peroxisome proliferator-activated receptor-alpha, ameliorates lipopolysaccharide-induced depressive-like behaviors by preventing neuroinflammation and oxido-nitrosative stress in mice

Yang R, et al.

Pharmacology, Biochemistry, and Behavior, 153, 97-104 (2017)

PPAR-alpha activation mediates innate host defense through induction of TFEB and lipid catabolism

Kim YS, et al.

Journal of Immunology, 198(8), 3283-3295 (2017)

Peroxisome proliferator-activated receptor alpha induction of uncoupling protein 2 protects against acetaminophen-induced liver toxicity.

Andrew D Patterson et al.

Hepatology (Baltimore, Md.), 56(1), 281-290 (2012-02-10)

Acetaminophen (APAP) overdose causes acute liver failure in humans and rodents due in part to the destruction of mitochondria as a result of increased oxidative stress followed by hepatocellular necrosis. Activation of the peroxisome proliferator-activated receptor alpha (PPARα), a member

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