CAS 50892-23-4|Wy-14643

Introduction：Basic information about CAS 50892-23-4|Wy-14643, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Wy-14643 BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles27
8. Synonyms

Common Name	Wy-14643
CAS Number	50892-23-4	Molecular Weight	323.798
Density	1.4±0.1 g/cm3	Boiling Point	514.4±50.0 °C at 760 mmHg
Molecular Formula	C₁₄H₁₄ClN₃O₂S	Melting Point	155°C
MSDS	USA	Flash Point	264.9±30.1 °C
Symbol	GHS07, GHS08	Signal Word	Danger

Names

Name	pirinixic acid
Synonym	More Synonyms

Wy-14643 BiologicalActivity

Description	Pirinixic acid (Wy-14643) is a potent agonist of PPARα, with EC50s of 0.63 μM, 32 μM for murine PPARα and PPARγ, and 5.0 μM, 60 μM, 35 μM for human PPARα, PPARγ and PPARδ, respectively.
Related Catalog	Signaling Pathways >>Cell Cycle/DNA Damage >>PPARResearch Areas >>Inflammation/ImmunologyResearch Areas >>Metabolic Disease
Target	PPARα:0.63 μM (EC50) PPARγ:32 μM (EC50)
In Vitro	Pirinixic acid (Wy-14643) is an agonist of PPARα, with EC50s of 0.63 μM, 32 μM for murine PPARα and PPARγ, and 5.0 μM, 60 μM, 35 μM for human PPARα, PPARγ and PPARδ, respectively[1]. Pirinixic acid (Wy-14643; 0, 10, 100 μM) enhances protein expression of PPAR-α in synovial fibroblasts. Pirinixic acid (0, 10, 100 μM) shows inhibitroy effects on NO and PGE2 production in LPS-stimulated synovial fibroblasts. Pirinixic acid also effectively downregulates expression of inflammatory mediators such as VCAM-1, ICAM-1, ET-1, and TF in synovial fibroblasts, blocks LPS-induced NF-kB activation, IkB phosphorylation, and NF-kB nuclear translocation in synovial fibroblasts, but Pirinixic acid shows no effects in PPAR-α silenced cells[2].
In Vivo	Pirinixic acid (Wy-14643; 10 mg/kg, i.v.) decreases hepatic injury and lipid peroxidation (MDA) levels in obese rats. Pirinixic acid also causes increased SIRT1 activity in Sham and ischemia-reperfusion (IR) group, but shows no effects on SIRT3 protein expression. Pirinixic acid enhances NAD+, and ATP levels, and prevents endoplasmic reticulum stress (ERS) in rats[3].
Cell Assay	Synovial fibroblasts are treated with LPS (100 μg/mL) in the presence or absence of Pirinixic acid. PPAR-α siRNA-transfected cells are also treated with LPS (100 μg/mL) together with Pirinixic acid. After stimulation, the production of NO is determined using Griess reagents. Briefly, 300 μL of supernatant is mixed with 100 μL of Griess reagent and 2.6 mL of deionized water. The mixture is incubated for 30 min at room temperature, and the absorbance at 548 nm is measured. The concentrations of NO in the supernatants are calculated from a standard curve[2].
Animal Admin	Synovial fibroblasts are treated with LPS (100 μg/mL) in the presence or absence of Wy-14643. PPAR-α siRNA-transfected cells are also treated with LPS (100 μg/mL) together with Wy-14643. After stimulation, the production of NO is determined using Griess reagents. Briefly, 300 μL of supernatant is mixed with 100 μL of Griess reagent and 2.6 mL of deionized water. The mixture is incubated for 30 min at room temperature, and the absorbance at 548 nm is measured. The concentrations of NO in the supernatants are calculated from a standard curve[2].
References	[1]. Willson TM, et al. The PPARs: from orphan receptors to drug discovery. J Med Chem. 2000 Feb 24;43(4):527-50. [2]. Huang D, et al. PPAR-α Agonist WY-14643 Inhibits LPS-Induced Inflammation in Synovial Fibroblasts via NF-kB Pathway. J Mol Neurosci. 2016 Aug;59(4):544-53. [3]. Pantazi E, et al. PPARα Agonist WY-14643 Induces SIRT1 Activity in Rat Fatty Liver Ischemia-Reperfusion Injury. Biomed Res Int. 2015;2015:894679.

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Boiling Point	514.4±50.0 °C at 760 mmHg
Melting Point	155°C
Molecular Formula	C₁₄H₁₄ClN₃O₂S
Molecular Weight	323.798
Flash Point	264.9±30.1 °C
Exact Mass	323.049530
PSA	100.41000
LogP	4.92
Vapour Pressure	0.0±1.4 mmHg at 25°C
Index of Refraction	1.658
InChIKey	SZRPDCCEHVWOJX-UHFFFAOYSA-N
SMILES	Cc1cccc(Nc2cc(Cl)nc(SCC(=O)O)n2)c1C
Storage condition	Store at RT

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AG2915000

CHEMICAL NAME :: Acetic acid, ((4-chloro-6-(2,3-xylidino)-2-pyrimidinyl)thio)-

CAS REGISTRY NUMBER :: 50892-23-4

BEILSTEIN REFERENCE NO. :: 0759945

LAST UPDATED :: 199806

DATA ITEMS CITED :: 23

MOLECULAR FORMULA :: C14-H14-Cl-N3-O2-S

MOLECULAR WEIGHT :: 323.82

WISWESSER LINE NOTATION :: T6N CNJ BS1VQ DG FMR B1 C1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1050 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 330 mg/kg/8W-C

TOXIC EFFECTS :: Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - hepatic microsomal mixed oxidase (dealkylation, hydroxylation, etc.)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 126 mg/kg/21D-C

TOXIC EFFECTS :: Liver - changes in liver weight Related to Chronic Data - changes in prostate weight Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1092 mg/kg/26W-C

TOXIC EFFECTS :: Gastrointestinal - changes in structure or function of endocrine pancreas Liver - changes in liver weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - hepatic microsomal mixed oxidase (dealkylation, hydroxylation, etc.)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1545 mg/kg/2Y-C

TOXIC EFFECTS :: Blood - pigmented or nucleated red blood cells Blood - changes in platelet count Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 22 gm/kg/1Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 37 gm/kg/62W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 46 gm/kg/65W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 27 gm/kg/64W-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 29 gm/kg/69W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors

TYPE OF TEST :: Morphological transformation

TYPE OF TEST :: Unscheduled DNA synthesis

MUTATION DATA

TYPE OF TEST :: Morphological transformation

TEST SYSTEM :: Rodent - hamster Embryo

DOSE/DURATION :: 85 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 356,85,1996

Safety Information

Symbol	GHS07, GHS08
Signal Word	Danger
Hazard Statements	H302-H315-H319-H335-H350
Precautionary Statements	P201-P261-P305 + P351 + P338-P308 + P313
Personal Protective Equipment	Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes	T
Risk Phrases	45-22-36/37/38
Safety Phrases	S26;S45;S53;S36/S37/S39
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	AG2915000
HS Code	2933599090

Customs

HS Code	2933599090
Summary	2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles27

Activation of peroxisome proliferator activated receptor alpha ameliorates ethanol mediated liver fibrosis in mice.

Lipids Health Dis. 12 , 11, (2013)

Peroxisome proliferator activated receptor alpha (PPARα) ameliorates ethanol induced hepatic steatohepatitis. However, its role in alcoholic liver fibrosis has not been fully clarified. The aim of thi...

Muscle lipogenesis balances insulin sensitivity and strength through calcium signaling.

J. Clin. Invest. 123(3) , 1229-40, (2013)

Exogenous dietary fat can induce obesity and promote diabetes, but endogenous fat production is not thought to affect skeletal muscle insulin resistance, an antecedent of metabolic disease. Unexpected...

Genetic ablation of solute carrier family 7a3a leads to hepatic steatosis in zebrafish during fasting.

Hepatology 60(6) , 1929-41, (2014)

Nonalcoholic fatty liver disease (NAFLD) is the most common chronic liver disorder caused by abnormal lipid metabolisms, such as reduced hepatic fatty acid oxidation (FAO), but intracellular control o...

Synonyms

acetic acid, [[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]thio]-

[4-Chloro-6-(2,3-xylidino)-2-pyriMidinylthio]acetic Acid

WY-14643

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

2-[4-chloro-6-(2,3-dimethylanilino)pyrimidin-2-yl]sulfanylacetic acid

({4-Chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl}sulfanyl)acetic acid

Wyeth 14643

({4-Chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl}sulfanyl)acetic acid

Acetic acid, 2-[[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]thio]-

T6N CNJ BS1VQ DMR B1 C1& FG

pirinixic acid

MFCD00191335

WY14643

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