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50892-23-4

50892-23-4 structure
50892-23-4 structure
  • Name: Wy-14643
  • Chemical Name: pirinixic acid
  • CAS Number: 50892-23-4
  • Molecular Formula: C14H14ClN3O2S
  • Molecular Weight: 323.798
  • Catalog: Biochemical Inhibitor Metabolism PPAR activator
  • Create Date: 2018-08-16 11:15:44
  • Modify Date: 2024-01-02 18:06:53
  • 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.

Name pirinixic acid
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
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
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.

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
Storage condition Store at RT

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
Symbol GHS07 GHS08
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
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%