Name | pirinixic acid |
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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. |
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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 |
Density | 1.4±0.1 g/cm3 |
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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
HEALTH HAZARD DATAACUTE TOXICITY DATA
MUTATION DATA
|
Symbol |
GHS07, GHS08 |
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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 |
~80% 50892-23-4 |
Literature: d'Atri; Gomarasca; Resnati; Tronconi; Scolastico; Sirtori Journal of Medicinal Chemistry, 1984 , vol. 27, # 12 p. 1621 - 1629 |
~% 50892-23-4 |
Literature: Santilli; Arthur A.; Scotese; Anthony C.; Tomarelli; Rudolph M. Patent: US3940394 A1, 1976 ; |
~% 50892-23-4 |
Literature: d'Atri; Gomarasca; Resnati; Tronconi; Scolastico; Sirtori Journal of Medicinal Chemistry, 1984 , vol. 27, # 12 p. 1621 - 1629 |
~% 50892-23-4 |
Literature: d'Atri; Gomarasca; Resnati; Tronconi; Scolastico; Sirtori Journal of Medicinal Chemistry, 1984 , vol. 27, # 12 p. 1621 - 1629 |
~% 50892-23-4 |
Literature: Thieme, Theresa M.; Steri, Ramona; Proschak, Ewgenij; Paulke, Alexander; Schneider, Gisbert; Schubert-Zsilavecz, Manfred Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 8 p. 2469 - 2473 |
Precursor 3 | |
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DownStream 2 | |
HS Code | 2933599090 |
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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% |