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
| Molecular Formula | C28H24F3NO6 |
| Molecular Weight | 527.4885 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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. | 2009-07-09 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:57:25 GMT 2025
by
admin
on
Mon Mar 31 17:57:25 GMT 2025
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| Record UNII |
J17152066B
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| Record Status |
Validated (UNII)
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668455-28-5
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J17152066B
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MK-0533
Created by
admin on Mon Mar 31 17:57:25 GMT 2025 , Edited by admin on Mon Mar 31 17:57:25 GMT 2025
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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
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CHEMBL490029
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DB15242
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admin on Mon Mar 31 17:57:25 GMT 2025 , Edited by admin on Mon Mar 31 17:57:25 GMT 2025
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SOLVATE->ANHYDROUS |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |
Indication: Type 2 diabetes mellitus; Focus: Therapeutic Use; Sponsors: Merck & Co, Merck Sharp & Dohme; Most Recent Events: 05 Oct 2008 Actual start date Oct 2007 to Jun 2006 as reported by CT.gov, 05 Oct 2008 Planned end date added (Sep 2007) as reported by CT.gov, 30 Oct 2007 New trial record.
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ACTIVE MOIETY |
Class: Anti-hyperglycaemic;
Mechanism of Action: Undefined mechanism; Highest Development Phase: Discontinued for Diabetes mellitus; Most Recent Events: 01 Aug 2006 Phase-II clinical trials in Diabetes mellitus in USA (unspecified route), 15 Feb 2006 Phase-I clinical trials in Diabetes mellitus in USA (unspecified route)
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ACTIVE MOIETY |
In comparison with PPARgamma full agonists, SPPARgammaM 6 (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.
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