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 |
|---|---|---|
| Identification of novel peroxisome proliferator-activated receptor alpha (PPARalpha) target genes in mouse liver using cDNA microarray analysis. | 2001 |
|
| Altered expression of the carboxylesterases ES-4 and ES-10 by peroxisome proliferator chemicals. | 2001 Aug 28 |
|
| Regulation of p85alpha phosphatidylinositol-3-kinase expression by peroxisome proliferator-activated receptors (PPARs) in human muscle cells. | 2001 Aug 3 |
|
| Effects of bezafibrate on beta-cell function of rat pancreatic islets. | 2001 Aug 31 |
|
| Differential regulation of adipocytokine mRNAs by rosiglitazone in db/db mice. | 2001 Aug 31 |
|
| Activators of peroxisome proliferator-activated receptors protect human skin from ultraviolet-B-light-induced inflammation. | 2001 Dec |
|
| Peroxisome proliferator-activated receptor alpha (PPAR alpha) agonist, WY-14,643, increased transcription of myosin light chain-2 in cardiomyocytes. | 2001 Dec |
|
| Selective modification of pyruvate dehydrogenase kinase isoform expression in rat pancreatic islets elicited by starvation and activation of peroxisome proliferator-activated receptor-alpha: implications for glucose-stimulated insulin secretion. | 2001 Dec |
|
| Antagonism of the actions of peroxisome proliferator-activated receptor-alpha by bile acids. | 2001 Dec 14 |
|
| The transcription of the peroxisome proliferator-activated receptor alpha gene is regulated by protein kinase C. | 2001 Dec 15 |
|
| Unique renal tubule changes induced in rats and mice by the peroxisome proliferators 2,4-dichlorophenoxyacetic acid (2,4-D) and WY-14643. | 2001 Jul-Aug |
|
| Limited cooperation between peroxisome proliferator-activated receptors and retinoid X receptor agonists in sebocyte growth and development. | 2001 Nov |
|
| 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 |
|
| Human peroxisome proliferator-activated receptor alpha (PPARalpha) supports the induction of peroxisome proliferation in PPARalpha-deficient mouse liver. | 2001 Nov 9 |
|
| Activation of the peroxisome proliferator-activated receptor-alpha enhances cell death in cultured cerebellar granule cells. | 2001 Oct 15 |
|
| Stabilization of peroxisome proliferator-activated receptor alpha by the ligand. | 2001 Oct 19 |
|
| Phenobarbital, oxazepam and Wyeth 14,643 cause DNA damage as measured by the Comet assay. | 2001 Sep |
|
| Comparison of the mutant frequencies and mutation spectra of three non-genotoxic carcinogens, oxazepam, phenobarbital, and Wyeth 14,643, at the lambdacII locus in Big Blue transgenic mice. | 2001 Sep 15 |
|
| Adaptive increase in pyruvate dehydrogenase kinase 4 during starvation is mediated by peroxisome proliferator-activated receptor alpha. | 2001 Sep 21 |
|
| Effect of peroxisome proliferators on the methylation and protein level of the c-myc protooncogene in B6C3F1 mice liver. | 2002 |
|
| Peroxisome proliferators activate growth regulatory pathways largely via peroxisome proliferator-activated receptor alpha-independent mechanisms. | 2002 Apr |
|
| PPAR activators as antiinflammatory mediators in human T lymphocytes: implications for atherosclerosis and transplantation-associated arteriosclerosis. | 2002 Apr 5 |
|
| Characterization of the adipose tissue atrophy induced by peroxisome proliferators in mice. | 2002 Feb |
|
| Nimesulide, a preferential cyclooxygenase 2 inhibitor, suppresses peroxisome proliferator-activated receptor induction of cyclooxygenase 2 gene expression in human synovial fibroblasts: evidence for receptor antagonism. | 2002 Feb |
|
| Regulation of pyruvate dehydrogenase kinase expression by peroxisome proliferator-activated receptor-alpha ligands, glucocorticoids, and insulin. | 2002 Feb |
|
| The role of hepatocyte RXR alpha in xenobiotic-sensing nuclear receptor-mediated pathways. | 2002 Feb |
|
| Topical peroxisome proliferator activated receptor-alpha activators reduce inflammation in irritant and allergic contact dermatitis models. | 2002 Jan |
|
| Characterization of an acyl-coA thioesterase that functions as a major regulator of peroxisomal lipid metabolism. | 2002 Jan 11 |
|
| PPARalpha and PPARdelta activators inhibit cytokine-induced nuclear translocation of NF-kappaB and expression of VCAM-1 in EAhy926 endothelial cells. | 2002 Jan 25 |
|
| Microarray analysis of gene expression changes in mouse liver induced by peroxisome proliferator- activated receptor alpha agonists. | 2002 Jan 25 |
|
| Advantages of glutamate dehydrogenase as a blood biomarker of acute hepatic injury in rats. | 2002 Jul |
|
| Ligands of the peroxisome proliferator-activated receptor-PPAR-a reduce myocardial infarct size. | 2002 Jul |
|
| Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size. | 2002 Jul |
|
| Mechanisms involved in responses to the poroxisome proliferator WY-14,643 on gap junctional intercellular communication in V79 hamster fibroblasts. | 2002 Jul 1 |
|
| Interactions of fluorochemicals with rat liver fatty acid-binding protein. | 2002 Jul 15 |
|
| WY14,643, a peroxisome proliferator-activated receptor alpha (PPARalpha ) agonist, improves hepatic and muscle steatosis and reverses insulin resistance in lipoatrophic A-ZIP/F-1 mice. | 2002 Jul 5 |
|
| Peroxisome proliferator-activated receptor agonists inhibit inflammatory edema and hyperalgesia. | 2002 Jun |
|
| Induction of apoptosis in human and rat glioma by agonists of the nuclear receptor PPARgamma. | 2002 Jun |
|
| Gene expression analysis reveals chemical-specific profiles. | 2002 Jun |
|
| Effects of peroxisome proliferator-activated receptor agonists on LPS-induced neuronal death in mixed cortical neurons: associated with iNOS and COX-2. | 2002 Jun 21 |
|
| Influence of peroxisome proliferator-activated receptor alpha agonists on the intracellular turnover and secretion of apolipoprotein (Apo) B-100 and ApoB-48. | 2002 Jun 21 |
|
| Potentiation of TNF-alpha-stimulated group IIA phospholipase A(2) expression by peroxisome proliferator-activated receptor alpha activators in rat mesangial cells. | 2002 Mar |
|
| Mechanism for peroxisome proliferator-activated receptor-alpha activator-induced up-regulation of UCP2 mRNA in rodent hepatocytes. | 2002 Mar 15 |
|
| Differential effects of gemfibrozil on migration, proliferation and proteoglycan production in human vascular smooth muscle cells. | 2002 May |
|
| Selective inhibition of cyclooxygenase-2 expression by 15-deoxy-Delta(12,14)(12,14)-prostaglandin J(2) in activated human astrocytes, but not in human brain macrophages. | 2002 May 1 |
|
| Involvement of the peroxisome proliferator-activated receptor alpha in the immunomodulation caused by peroxisome proliferators in mice. | 2002 May 15 |
|
| PPAR activators inhibit endothelial cell migration by targeting Akt. | 2002 May 24 |
|
| 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 UTC 2023
by
admin
on
Sat Dec 16 17:52:34 UTC 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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DTXSID4020290
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