Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H14ClN3O2S |
| Molecular Weight | 323.798 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(C)C(NC2=CC(Cl)=NC(SCC(O)=O)=N2)=CC=C1
InChI
InChIKey=SZRPDCCEHVWOJX-UHFFFAOYSA-N
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)
| Molecular Formula | C14H14ClN3O2S |
| Molecular Weight | 323.798 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/21585347
https://en.wikipedia.org/wiki/Pirinixic_acid
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/21585347
https://en.wikipedia.org/wiki/Pirinixic_acid
Pirinixic acid is a PPARα ligand that can affect atherogenesis by modulating hepatic lipid metabolism and by acting directly on vascular tissue. PPARα activation is generally assumed to be the primary means by which Pirinixic acid produces its biological effects. Nevertheless, there is increasing evidence to suggest that Pirinixic acid is also capable of affecting cellular processes directly. It is under experimental investigation for prevention of severe cardiac dysfunction, cardiomyopathy and heart failure as a result of lipid accumulation within cardiac myocytes. Treatment is primarily aimed at individuals with an adipose triglyceride lipase (ATGL) enzyme deficiency or mutation. For example, cardiac contractility was improved by treating ATGL(-/-) mice with the Pirinixic acid.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Rosiglitazone (BRL49653), a PPARgamma-selective agonist, causes peroxisome proliferator-like liver effects in obese mice. | 1999 Jul |
|
| Peroxisome proliferators and fatty acids negatively regulate liver X receptor-mediated activity and sterol biosynthesis. | 2001 Apr |
|
| Peroxisome proliferator-activated receptor-alpha ligands inhibit cardiac lipoprotein lipase activity. | 2001 Aug |
|
| The transcription of the peroxisome proliferator-activated receptor alpha gene is regulated by protein kinase C. | 2001 Dec 15 |
|
| Effects of peroxisome proliferators on glutathione and glutathione-related enzymes in rats and hamsters. | 2001 Feb 15 |
|
| Fatty-acyl-CoA thioesters inhibit recruitment of steroid receptor co-activator 1 to alpha and gamma isoforms of peroxisome-proliferator-activated receptors by competing with agonists. | 2001 Jan 15 |
|
| PPARalpha activators inhibit tissue factor expression and activity in human monocytes. | 2001 Jan 16 |
|
| PPARalpha agonists inhibit tissue factor expression in human monocytes and macrophages. | 2001 Jan 16 |
|
| Identification of peroxisome proliferator-responsive human genes by elevated expression of the peroxisome proliferator-activated receptor alpha in HepG2 cells. | 2001 Jul 27 |
|
| Cloning of the human cholesteryl ester hydrolase promoter: identification of functional peroxisomal proliferator-activated receptor responsive elements. | 2001 Jun 22 |
|
| Tumor necrosis factor alpha is not required for WY14,643-induced cell proliferation. | 2001 Mar |
|
| Mono-(2-ethylhexyl) phthalate suppresses aromatase transcript levels and estradiol production in cultured rat granulosa cells. | 2001 May 1 |
|
| The short heterodimer partner receptor differentially modulates peroxisome proliferator-activated receptor alpha-mediated transcription from the peroxisome proliferator-response elements of the genes encoding the peroxisomal beta-oxidation enzymes acyl-CoA oxidase and hydratase-dehydrogenase. | 2001 May 15 |
|
| Fibrates suppress bile acid synthesis via peroxisome proliferator-activated receptor-alpha-mediated downregulation of cholesterol 7alpha-hydroxylase and sterol 27-hydroxylase expression. | 2001 Nov |
|
| Hepatocellular proliferation in response to a peroxisome proliferator does not require TNFalpha signaling. | 2001 Nov |
|
| Reactivation of peroxisome proliferator-activated receptor alpha is associated with contractile dysfunction in hypertrophied rat heart. | 2001 Nov 30 |
|
| Phenobarbital, oxazepam and Wyeth 14,643 cause DNA damage as measured by the Comet assay. | 2001 Sep |
|
| Effect of peroxisome proliferators on the methylation and protein level of the c-myc protooncogene in B6C3F1 mice liver. | 2002 |
|
| Characterization of an acyl-coA thioesterase that functions as a major regulator of peroxisomal lipid metabolism. | 2002 Jan 11 |
|
| Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size. | 2002 Jul |
|
| Induction of apoptosis in human and rat glioma by agonists of the nuclear receptor PPARgamma. | 2002 Jun |
|
| Inhibition of cytokine-induced matrix metalloproteinase 9 expression by peroxisome proliferator-activated receptor alpha agonists is indirect and due to a NO-mediated reduction of mRNA stability. | 2002 Sep 6 |
Patents
Sample Use Guides
0.02% w/w in food over 10 days or 0.1% w/w for 7 days.
intraperitoneal injection - 50 mg/kg or 80 mg/kg
Route of Administration:
Other
Mitochondria from the left ventricle of rats were similarly sensitive to 100 µM Wy14,643. In this case Wy14,643 inhibited state 3 respiration, which affected both respiratory capacity and the ADP phosphorylation state. As a result, oxidative phosphorylation is uncoupled by Wy14,643.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:52:34 GMT 2023
by
admin
on
Sat Dec 16 17:52:34 GMT 2023
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| Record UNII |
86C4MRT55A
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| Record Status |
Validated (UNII)
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| Record Version |
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C45175
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86C4MRT55A
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50892-23-4
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C006253
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C29866
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Pirinixic acid
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SUB09915MIG
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CHEMBL295416
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ACTIVE MOIETY |
