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 |
|---|---|---|
| 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. | 2002-09-06 |
|
| Interactions of fluorochemicals with rat liver fatty acid-binding protein. | 2002-07-15 |
|
| 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. | 2002-07-05 |
|
| Mechanisms involved in responses to the poroxisome proliferator WY-14,643 on gap junctional intercellular communication in V79 hamster fibroblasts. | 2002-07-01 |
|
| Advantages of glutamate dehydrogenase as a blood biomarker of acute hepatic injury in rats. | 2002-07 |
|
| Ligands of the peroxisome proliferator-activated receptor-PPAR-a reduce myocardial infarct size. | 2002-07 |
|
| Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size. | 2002-07 |
|
| Effects of peroxisome proliferator-activated receptor agonists on LPS-induced neuronal death in mixed cortical neurons: associated with iNOS and COX-2. | 2002-06-21 |
|
| Influence of peroxisome proliferator-activated receptor alpha agonists on the intracellular turnover and secretion of apolipoprotein (Apo) B-100 and ApoB-48. | 2002-06-21 |
|
| Peroxisome proliferator-activated receptor agonists inhibit inflammatory edema and hyperalgesia. | 2002-06 |
|
| Induction of apoptosis in human and rat glioma by agonists of the nuclear receptor PPARgamma. | 2002-06 |
|
| Gene expression analysis reveals chemical-specific profiles. | 2002-06 |
|
| PPAR activators inhibit endothelial cell migration by targeting Akt. | 2002-05-24 |
|
| Involvement of the peroxisome proliferator-activated receptor alpha in the immunomodulation caused by peroxisome proliferators in mice. | 2002-05-15 |
|
| 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. | 2002-05-01 |
|
| Differential effects of gemfibrozil on migration, proliferation and proteoglycan production in human vascular smooth muscle cells. | 2002-05 |
|
| PPAR activators as antiinflammatory mediators in human T lymphocytes: implications for atherosclerosis and transplantation-associated arteriosclerosis. | 2002-04-05 |
|
| Peroxisome proliferators activate growth regulatory pathways largely via peroxisome proliferator-activated receptor alpha-independent mechanisms. | 2002-04 |
|
| Mechanism for peroxisome proliferator-activated receptor-alpha activator-induced up-regulation of UCP2 mRNA in rodent hepatocytes. | 2002-03-15 |
|
| Potentiation of TNF-alpha-stimulated group IIA phospholipase A(2) expression by peroxisome proliferator-activated receptor alpha activators in rat mesangial cells. | 2002-03 |
|
| Characterization of the adipose tissue atrophy induced by peroxisome proliferators in mice. | 2002-02 |
|
| 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. | 2002-02 |
|
| Regulation of pyruvate dehydrogenase kinase expression by peroxisome proliferator-activated receptor-alpha ligands, glucocorticoids, and insulin. | 2002-02 |
|
| The role of hepatocyte RXR alpha in xenobiotic-sensing nuclear receptor-mediated pathways. | 2002-02 |
|
| PPARalpha and PPARdelta activators inhibit cytokine-induced nuclear translocation of NF-kappaB and expression of VCAM-1 in EAhy926 endothelial cells. | 2002-01-25 |
|
| Microarray analysis of gene expression changes in mouse liver induced by peroxisome proliferator- activated receptor alpha agonists. | 2002-01-25 |
|
| Characterization of an acyl-coA thioesterase that functions as a major regulator of peroxisomal lipid metabolism. | 2002-01-11 |
|
| Topical peroxisome proliferator activated receptor-alpha activators reduce inflammation in irritant and allergic contact dermatitis models. | 2002-01 |
|
| Effect of peroxisome proliferators on the methylation and protein level of the c-myc protooncogene in B6C3F1 mice liver. | 2002 |
|
| The transcription of the peroxisome proliferator-activated receptor alpha gene is regulated by protein kinase C. | 2001-12-15 |
|
| Antagonism of the actions of peroxisome proliferator-activated receptor-alpha by bile acids. | 2001-12-14 |
|
| Activators of peroxisome proliferator-activated receptors protect human skin from ultraviolet-B-light-induced inflammation. | 2001-12 |
|
| Peroxisome proliferator-activated receptor alpha (PPAR alpha) agonist, WY-14,643, increased transcription of myosin light chain-2 in cardiomyocytes. | 2001-12 |
|
| 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. | 2001-12 |
|
| Reactivation of peroxisome proliferator-activated receptor alpha is associated with contractile dysfunction in hypertrophied rat heart. | 2001-11-30 |
|
| Human peroxisome proliferator-activated receptor alpha (PPARalpha) supports the induction of peroxisome proliferation in PPARalpha-deficient mouse liver. | 2001-11-09 |
|
| Limited cooperation between peroxisome proliferator-activated receptors and retinoid X receptor agonists in sebocyte growth and development. | 2001-11 |
|
| Fibrates suppress bile acid synthesis via peroxisome proliferator-activated receptor-alpha-mediated downregulation of cholesterol 7alpha-hydroxylase and sterol 27-hydroxylase expression. | 2001-11 |
|
| Hepatocellular proliferation in response to a peroxisome proliferator does not require TNFalpha signaling. | 2001-11 |
|
| Stabilization of peroxisome proliferator-activated receptor alpha by the ligand. | 2001-10-19 |
|
| Activation of the peroxisome proliferator-activated receptor-alpha enhances cell death in cultured cerebellar granule cells. | 2001-10-15 |
|
| Adaptive increase in pyruvate dehydrogenase kinase 4 during starvation is mediated by peroxisome proliferator-activated receptor alpha. | 2001-09-21 |
|
| Unique renal tubule changes induced in rats and mice by the peroxisome proliferators 2,4-dichlorophenoxyacetic acid (2,4-D) and WY-14643. | 2001-09-19 |
|
| 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. | 2001-09-15 |
|
| Phenobarbital, oxazepam and Wyeth 14,643 cause DNA damage as measured by the Comet assay. | 2001-09 |
|
| Effects of bezafibrate on beta-cell function of rat pancreatic islets. | 2001-08-31 |
|
| Differential regulation of adipocytokine mRNAs by rosiglitazone in db/db mice. | 2001-08-31 |
|
| Altered expression of the carboxylesterases ES-4 and ES-10 by peroxisome proliferator chemicals. | 2001-08-28 |
|
| Regulation of p85alpha phosphatidylinositol-3-kinase expression by peroxisome proliferator-activated receptors (PPARs) in human muscle cells. | 2001-08-03 |
|
| Identification of novel peroxisome proliferator-activated receptor alpha (PPARalpha) target genes in mouse liver using cDNA microarray analysis. | 2001 |
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
Wed Apr 02 09:43:11 GMT 2025
by
admin
on
Wed Apr 02 09:43:11 GMT 2025
|
| Record UNII |
86C4MRT55A
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C45175
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
86C4MRT55A
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
50892-23-4
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
C006253
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
C29866
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
Pirinixic acid
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
SUB09915MIG
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
4871
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
100000081649
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
5694
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
310038
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
32509
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
CHEMBL295416
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
DTXSID4020290
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY | |||
|
8056
Created by
admin on Wed Apr 02 09:43:11 GMT 2025 , Edited by admin on Wed Apr 02 09:43:11 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
TRANSPORTER -> INHIBITOR |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
