Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C28H24F3NO6 |
| Molecular Weight | 527.4885 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@@H](OC1=CC=CC(=C1)N2C(C)=C(C(=O)C3=CC=C(OC)C=C3)C4=CC=C(OC(F)(F)F)C=C24)C(O)=O
InChI
InChIKey=STWITCBWQHTJFJ-XMMPIXPASA-N
InChI=1S/C28H24F3NO6/c1-4-24(27(34)35)37-20-7-5-6-18(14-20)32-16(2)25(26(33)17-8-10-19(36-3)11-9-17)22-13-12-21(15-23(22)32)38-28(29,30)31/h5-15,24H,4H2,1-3H3,(H,34,35)/t24-/m1/s1
MK-0533 is a novel selective peroxisome proliferator-activated receptor gamma modulator for the treatment of type 2 diabetes mellitus. In comparison with PPARγ full agonists, MK-0533 displayed diminished maximal activity (partial agonism) in cell-based transcription activation assays and attenuated gene signatures in adipose tissue. MK-0533 exhibited comparable efficacy to rosiglitazone and pioglitazone in vivo. However, with regard to the induction of untoward events, MK-0533 displayed no cardiac hypertrophy, attenuated increases in brown adipose tissue, minimal increases in plasma volume, and no increases in extracellular fluid volume in vivo. MK-0533 was teste in phase II clinical trials but future development was discontinued.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Discovery of (2R)-2-(3-{3-[(4-Methoxyphenyl)carbonyl]-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl}phenoxy)butanoic acid (MK-0533): a novel selective peroxisome proliferator-activated receptor gamma modulator for the treatment of type 2 diabetes mellitus with a reduced potential to increase plasma and extracellular fluid volume. | 2009 Jul 9 |
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668455-28-5
Created by
admin on Fri Dec 15 15:25:46 UTC 2023 , Edited by admin on Fri Dec 15 15:25:46 UTC 2023
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J17152066B
Created by
admin on Fri Dec 15 15:25:46 UTC 2023 , Edited by admin on Fri Dec 15 15:25:46 UTC 2023
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MK-0533
Created by
admin on Fri Dec 15 15:25:46 UTC 2023 , Edited by admin on Fri Dec 15 15:25:46 UTC 2023
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PRIMARY | Description: MK-0533 is a novel selective peroxisome proliferator-activated receptor gamma modulator for the treatment of type 2 diabetes mellitus with a reduced potential to increase plasma and extracellular fluid volume. MK0533 displayed diminished maximal activity (partial agonism) in cell-based transcription activation assays and attenuated gene signatures in adipose tissue. Compound 6 exhibited comparable efficacy to rosiglitazone and pioglitazone in vivo. However, with regard to the induction of untoward events, 6 displayed no cardiac hypertrophy, attenuated increases in brown adipose tissue, minimal increases in plasma volume, and no increases in extracellular fluid volume in vivo. Further investigation of 6 is warranted to determine if the improvement in mechanism-based side effects observed in preclinical species will be recapitulated in humans. (10/24/2015). | ||
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11678534
Created by
admin on Fri Dec 15 15:25:46 UTC 2023 , Edited by admin on Fri Dec 15 15:25:46 UTC 2023
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CHEMBL490029
Created by
admin on Fri Dec 15 15:25:46 UTC 2023 , Edited by admin on Fri Dec 15 15:25:46 UTC 2023
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DB15242
Created by
admin on Fri Dec 15 15:25:46 UTC 2023 , Edited by admin on Fri Dec 15 15:25:46 UTC 2023
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
