MK-0533

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 522456

CAS#: 668455-28-5

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.


Chemical Structure

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MK-0533
CAS# 668455-28-5

Theoretical Analysis

MedKoo Cat#: 522456
Name: MK-0533
CAS#: 668455-28-5
Chemical Formula: C28H24F3NO6
Exact Mass: 527.15557
Molecular Weight: 527.5
Elemental Analysis: C, 63.76; H, 4.59; F, 10.80; N, 2.66; O, 18.20

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Synonym: MK-0533; MK 0533; MK0533.

IUPAC/Chemical Name: (R)-2-(3-(3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl)phenoxy)butanoic acid

InChi Key: STWITCBWQHTJFJ-XMMPIXPASA-N

InChi Code: 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

SMILES Code: CC[C@@H](OC1=CC=CC(N2C(C)=C(C(C3=CC=C(OC)C=C3)=O)C4=C2C=C(OC(F)(F)F)C=C4)=C1)C(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 527.5 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Balakumar P, Kathuria S. Submaximal PPARγ activation and endothelial dysfunction: new perspectives for the management of cardiovascular disorders. Br J Pharmacol. 2012 Aug;166(7):1981-92. doi: 10.1111/j.1476-5381.2012.01938.x. Review. PubMed PMID: 22404217; PubMed Central PMCID: PMC3402765.

2: Acton JJ 3rd, Akiyama TE, Chang CH, Colwell L, Debenham S, Doebber T, Einstein M, Liu K, McCann ME, Moller DE, Muise ES, Tan Y, Thompson JR, Wong KK, Wu M, Xu L, Meinke PT, Berger JP, Wood HB. 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. J Med Chem. 2009 Jul 9;52(13):3846-54. doi: 10.1021/jm900097m. Erratum in: J Med Chem. 2013 Nov 27;56(22):9368. Tan, Yugen [corrected to Tan, Yejun]. PubMed PMID: 19507861.

3: Xie W, Mullett WM, Miller-Stein CM, Pawliszyn J. Automation of in-tip solid-phase microextraction in 96-well format for the determination of a model drug compound in human plasma by liquid chromatography with tandem mass spectrometric detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Feb 1;877(4):415-20. doi: 10.1016/j.jchromb.2008.12.036. Epub 2008 Dec 25. PubMed PMID: 19144575.