U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of MIFOBATE

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

HIDE SMILES / InChI

Description
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

Targets

Primary TargetPharmacologyConditionPotency
140.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Rosiglitazone and metformin have opposite effects on intestinal absorption of oligopeptides via the proton-dependent PepT1 transporter.
2012 Mar
Inhibitory effect of baicalin on iNOS and NO expression in intestinal mucosa of rats with acute endotoxemia.
2013
Patents

Patents

Sample Use Guides

100 mg three times per day for 3 days
Route of Administration: Oral
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.
Name Type Language
MIFOBATE
INN   USAN  
INN   USAN  
Official Name English
SR-202
Code English
DIMETHYL (P-CHLORO-.ALPHA.-HYDROXYBENZYL)PHOSPHONATE, DIMETHYL PHOSPHATE
Common Name English
CLANICLOR
Common Name English
CLENICOR
Brand Name English
MIFOBATE [USAN]
Common Name English
PHOSPHORIC ACID, (4-CHLOROPHENYL)(DIMETHOXYPHOSPHINYL)METHYL DIMETHYL ESTER
Common Name English
mifobate [INN]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID6045741
Created by admin on Fri Dec 15 15:17:44 GMT 2023 , Edited by admin on Fri Dec 15 15:17:44 GMT 2023
PRIMARY
FDA UNII
ZKA4OVV12E
Created by admin on Fri Dec 15 15:17:44 GMT 2023 , Edited by admin on Fri Dec 15 15:17:44 GMT 2023
PRIMARY
EVMPD
SUB08957MIG
Created by admin on Fri Dec 15 15:17:44 GMT 2023 , Edited by admin on Fri Dec 15 15:17:44 GMT 2023
PRIMARY
SMS_ID
100000080610
Created by admin on Fri Dec 15 15:17:44 GMT 2023 , Edited by admin on Fri Dec 15 15:17:44 GMT 2023
PRIMARY
INN
5352
Created by admin on Fri Dec 15 15:17:44 GMT 2023 , Edited by admin on Fri Dec 15 15:17:44 GMT 2023
PRIMARY
CAS
76541-72-5
Created by admin on Fri Dec 15 15:17:44 GMT 2023 , Edited by admin on Fri Dec 15 15:17:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL284768
Created by admin on Fri Dec 15 15:17:44 GMT 2023 , Edited by admin on Fri Dec 15 15:17:44 GMT 2023
PRIMARY
PUBCHEM
60910
Created by admin on Fri Dec 15 15:17:44 GMT 2023 , Edited by admin on Fri Dec 15 15:17:44 GMT 2023
PRIMARY
NCI_THESAURUS
C170175
Created by admin on Fri Dec 15 15:17:44 GMT 2023 , Edited by admin on Fri Dec 15 15:17:44 GMT 2023
PRIMARY