![[4-Chloro-6-(2,3-xylidino)-2-pyrimidinylthio]acetic acid structure, CAS 50892-23-4](/structures/20000/8951_1_50892_23_4.png)
CAS Number50892-23-4
Synonyms[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; pirinixic acid; MFCD00191335; WY14643
Molecular FormulaC14H14ClN3O2S
Molecular Weight323.80
Purity98%
Density1.4±0.1 g/cm3
Boiling Point514.4±50.0 °C at 760 mmHg
Melting Point155°C
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 50892-23-4 |
| Catalog No. | 2A-9008951 |
| Chinese Name | 匹立尼酸 |
| Synonyms | [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; pirinixic acid; MFCD00191335; WY14643 |
| Molecular Formula | C14H14ClN3O2S |
| Molecular Weight | 323.80 |
| Purity | 98 |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 514.4±50.0 °C at 760 mmHg |
| Melting Point | 155°C |
| Appearance | powder |
| Storage Condition | Keep the receptacle sealed, stored in a cool, dry |
| Application | Pirinixic acid (Wy-14643) is a potent PPARα agonist with EC50 values of 0.63 μM and 32 μM for mouse PPARα and PPARγ respectively, and EC50 values of 5.0 μM, 60 μM and 35 μM for human PPARα, PPARγ |
| HTC | 2933599090 |
| PubChem ID | 24892928 |
| MDL Number | MFCD00191335 |
| SMILES | 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | Transport |
| MSDS | msds/8951_1_50892_23_4.pdf |
| Bioactivity | 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 >> PPAR Research Areas >> Inflammation/Immunology Research 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 |
| Use of | 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. Properties Articles27 Name pirinixic acid Synonym More Synonyms Wy-14643 Biological Activity 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 >> PPAR Research Areas >> Inflammation/Immunology Research Areas >> Metabolic Disease 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]. 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 Exact Mass 323.049530 PSA 100.41000 Index of Refraction 1.658 InChIKey SZRPDCCEHVWOJX-UHFFFAOYSA-N Storage condition Store at RT |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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