Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H17ClO7P2 |
Molecular Weight | 358.649 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COP(=O)(OC)OC(C1=CC=C(Cl)C=C1)P(=O)(OC)OC
InChI
InChIKey=VQHUQHAPWMNBLP-UHFFFAOYSA-N
InChI=1S/C11H17ClO7P2/c1-15-20(13,16-2)11(19-21(14,17-3)18-4)9-5-7-10(12)8-6-9/h5-8,11H,1-4H3
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/18329752Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12665425 | https://www.ncbi.nlm.nih.gov/pubmed/3102663
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18329752
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12665425 | https://www.ncbi.nlm.nih.gov/pubmed/3102663
SR 202 is an antagonist of peroxisome proliferator-activated receptor γ (PPARγ) transcriptional activity induced by troglitazone but not of basal PPARγ activity. It is selective for PPARγ, not affecting basal or agonist-induced transcriptional activity of PPARα, PPARβ, or the farnesoid X receptor (FXR). It inhibits PPARγ-dependent differentiation of preadipocyte 3T3-L1 cells in a dose-dependent manner. SR 202 (400 mg/kg) decreases the amount of weight gained and white adipose tissue mass accumulated by mice fed a standard or high-fat diet for ten weeks and is associated with lower PPARγ mRNA levels. It protects against high-fat diet-induced insulin resistance in wild-type mice and improves insulin sensitivity in ob/ob mice.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18329752 |
140.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3102663
100 mg three times per day for 3 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12403851
3T3-L1 cells were cultured in DMEM supplemented by 10% bovine calf serum. Two days after reaching confluency, differentiation was induced in DMEM supplemented with 10% fetal calf serum and dexamethasone (1 _M)/IBMX (0.5 mM)/ insulin (10 _g/ml). After 48 h, the medium was changed with only the addition of insulin for an additional 2 d. Thereafter, the cells were grown in DMEM supplemented with 10% fetal calf serum. Alternatively, cells were also differentiated with BRL 49653 (25 nM) and insulin (5 mkg/ml). SR-202 or vehicle (H2O) was added 24 h before induction of differentiation. Medium was replenished with ligands every 2 d. Adipogenesis was determined by the staining of lipids with Oil Red O and by measuring the expression of adipocyte markers.
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ACTIVE MOIETY