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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

Molecular Formula C11H17ClO7P2
Molecular Weight 358.649
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:17:44 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:44 GMT 2023
Record UNII
ZKA4OVV12E
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ACTIVE MOIETY