Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H18F3NO3S2 |
Molecular Weight | 453.498 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(CSC2=CC=C(OCC(O)=O)C(C)=C2)SC(=N1)C3=CC=C(C=C3)C(F)(F)F
InChI
InChIKey=YDBLKRPLXZNVNB-UHFFFAOYSA-N
InChI=1S/C21H18F3NO3S2/c1-12-9-16(7-8-17(12)28-10-19(26)27)29-11-18-13(2)25-20(30-18)14-3-5-15(6-4-14)21(22,23)24/h3-9H,10-11H2,1-2H3,(H,26,27)
Molecular Formula | C21H18F3NO3S2 |
Molecular Weight | 453.498 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16625823Curator's Comment: description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800015062 | https://en.wikipedia.org/wiki/GW501516
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16625823
Curator's Comment: description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800015062 | https://en.wikipedia.org/wiki/GW501516
GW-501516 is a peroxisome proliferator-activator receptor-delta agonist for the potential treatment of dyslipidemia, hyperlipidemia, metabolic diseases and cardiovascular diseases. GW501516 treatment is associated with significant improvements in multiple lipid profile components (TG, LDL-C, HDL-C, free fatty acids and apoB, apoA-I and apoA-II) and a shift in LDL particle size from small dense to larger, less dense particles. Despite these promising early results, the further investigation and development of GW501516 was discontinued after observations in animal studies of its association with the rapid induction of cancers in several organs (liver, stomach, tongue, skin, bladder, ovaries, womb and testes).
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17167170
Curator's Comment: GW501516 have very poor ability in terms of brain penetration.
Known to be CNS penetrant in rodents. Human data not available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16625823 |
1.1 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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A selective peroxisome proliferator-activated receptor delta agonist promotes reverse cholesterol transport. | 2001 Apr 24 |
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PPAR delta: an uncompletely known nuclear receptor. | 2005 Feb |
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Nanomolar and micromolar effects of 15-deoxy-delta 12,14-prostaglandin J2 on amnion-derived WISH epithelial cells: differential roles of peroxisome proliferator-activated receptors gamma and delta and nuclear factor kappa B. | 2005 Jul |
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Gene expression profiling of potential peroxisome proliferator-activated receptor (PPAR) target genes in human hepatoblastoma cell lines inducibly expressing different PPAR isoforms. | 2005 Oct 3 |
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Role of AMP kinase and PPARdelta in the regulation of lipid and glucose metabolism in human skeletal muscle. | 2007 Jul 6 |
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The PPARdelta agonist, GW501516, promotes fatty acid oxidation but has no direct effect on glucose utilisation or insulin sensitivity in rat L6 skeletal muscle cells. | 2007 Oct 2 |
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Inflammatory pathways are activated during cardiomyocyte hypertrophy and attenuated by peroxisome proliferator-activated receptors PPARalpha and PPARdelta. | 2008 Oct 24 |
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Regulation of peroxisome proliferator-activated receptor-alpha by MDM2. | 2009 Mar |
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Synthesis of isosteric selenium analog of the PPARbeta/delta agonist GW501516 and comparison of biological activity. | 2010 Jul 15 |
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Functional characterization of peroxisome proliferator-activated receptor-β/δ expression in colon cancer. | 2011 Nov |
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Activation of PPARδ prevents endothelial dysfunction induced by overexpression of amyloid-β precursor protein. | 2012 Dec 1 |
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Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach. | 2014 Jul |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22814748
12 weeks of treatment with 2.5 mg, 5.0 mg or 5,0 mg, 10 mg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11309497
In 1BR3N human skin fibroblasts, the 1 uM of GW501516 produced a 3.4-fold increase in ABCA1 expression and a 2-fold increase in apoA1-specific cholesterol efflux. In FHS74 human intestinal cells, the 1 uM of GW501516 produced a 2.1-fold increase in ABCA1 expression.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:34:31 UTC 2023
by
admin
on
Fri Dec 15 15:34:31 UTC 2023
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Record UNII |
7I2HA1NU22
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
3989 (Number of products:9)
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DSLD |
3986 (Number of products:12)
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7I2HA1NU22
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DTXSID3041037
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73726
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GW501516
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9803963
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DB05416
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317318-70-0
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TARGET -> AGONIST |
Related Record | Type | Details | ||
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ACTIVE MOIETY |