MK-0767 | CAS#213252-19-8 | PPAR agonist

MedKoo Cat#: 525417 | Name: MK-0767

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Description:

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

MK-0767, also known as KRP297 and MK-767, is a PPAR agonist potentially for the treatment of type 2 diabetes and dyslipidemia. When administered to ob/ob mice, KRP-297 (0.3 to 10 mg/kg) decreased plasma glucose and insulin levels and improved the impaired insulin-stimulated 2DG uptake in soleus muscle in a dose-dependent manner. KRP-297 treatment is useful to prevent the development of diabetic syndromes in addition to ameliorating the impaired glucose transport in skeletal muscle.

Chemical Structure

MK-0767

CAS#213252-19-8

Theoretical Analysis

MedKoo Cat#: 525417

Name: MK-0767

CAS#: 213252-19-8

Chemical Formula: C20H17F3N2O4S

Exact Mass: 438.0861

Molecular Weight: 438.42

Elemental Analysis: C, 54.79; H, 3.91; F, 13.00; N, 6.39; O, 14.60; S, 7.31

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 550.00	2 Weeks
10mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

KRP297; KRP-297; KRP 297; L 410198; L410198; L-410198; MK-0767; MK0767; MK 0767; MK-767; MK767; MK 767;

IUPAC/Chemical Name

5-((2,4-Dioxo-5-thiazolidinyl)methyl)-2-methoxy-N-((4-(trifluoromethyl)phenyl)methyl)benzamide

InChi Key

NFFXEUUOMTXWCX-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H17F3N2O4S/c1-29-15-7-4-12(9-16-18(27)25-19(28)30-16)8-14(15)17(26)24-10-11-2-5-13(6-3-11)20(21,22)23/h2-8,16H,9-10H2,1H3,(H,24,26)(H,25,27,28)

SMILES Code

O=C(NCC1=CC=C(C(F)(F)F)C=C1)C2=CC(CC(SC(N3)=O)C3=O)=CC=C2OC

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

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

KRP-297 is a PPARα and PPARγ agonist potentially for the treatment of type 2 diabetes and dyslipidemia.

In vitro activity:

In cell-based assays, MK-0767 produced potent activation of human PPARgamma and PPARalpha with a gamma:alpha potency ratio of approximately. Reference: Biochem Biophys Res Commun. 2004 May 28;318(2):323-8. https://pubmed.ncbi.nlm.nih.gov/15120604/

In vivo activity:

When administered to ob/ob mice, KRP-297 (0.3 to 10 mg/kg) decreased plasma glucose and insulin levels and improved the impaired insulin-stimulated 2DG uptake in soleus muscle in a dose-dependent manner. Moreover, KRP-297 prevented severe hyperglycemia and the marked decrease in pancreatic insulin content in db/db mice. Reference: Metabolism. 1999 Nov;48(11):1450-4. https://pubmed.ncbi.nlm.nih.gov/10582556/

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	22.81

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 438.42 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.

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

Formulation protocol:

1. Doebber TW, Kelly LJ, Zhou G, Meurer R, Biswas C, Li Y, Wu MS, Ippolito MC, Chao YS, Wang PR, Wright SD, Moller DE, Berger JP. MK-0767, a novel dual PPARalpha/gamma agonist, displays robust antihyperglycemic and hypolipidemic activities. Biochem Biophys Res Commun. 2004 May 28;318(2):323-8. doi: 10.1016/j.bbrc.2004.04.032. PMID: 15120604. 2. Murakami K, Tsunoda M, Ide T, Ohashi M, Mochizuki T. Amelioration by KRP-297, a new thiazolidinedione, of impaired glucose uptake in skeletal muscle from obese insulin-resistant animals. Metabolism. 1999 Nov;48(11):1450-4. doi: 10.1016/s0026-0495(99)90158-0. PMID: 10582556. 3. Murakami K, Tobe K, Ide T, Mochizuki T, Ohashi M, Akanuma Y, Yazaki Y, Kadowaki T. A novel insulin sensitizer acts as a coligand for peroxisome proliferator-activated receptor-alpha (PPAR-alpha) and PPAR-gamma: effect of PPAR-alpha activation on abnormal lipid metabolism in liver of Zucker fatty rats. Diabetes. 1998 Dec;47(12):1841-7. doi: 10.2337/diabetes.47.12.1841. PMID: 9836514.

In vitro protocol:

In vivo protocol:

1. Murakami K, Tsunoda M, Ide T, Ohashi M, Mochizuki T. Amelioration by KRP-297, a new thiazolidinedione, of impaired glucose uptake in skeletal muscle from obese insulin-resistant animals. Metabolism. 1999 Nov;48(11):1450-4. doi: 10.1016/s0026-0495(99)90158-0. PMID: 10582556. 2. Murakami K, Tobe K, Ide T, Mochizuki T, Ohashi M, Akanuma Y, Yazaki Y, Kadowaki T. A novel insulin sensitizer acts as a coligand for peroxisome proliferator-activated receptor-alpha (PPAR-alpha) and PPAR-gamma: effect of PPAR-alpha activation on abnormal lipid metabolism in liver of Zucker fatty rats. Diabetes. 1998 Dec;47(12):1841-7. doi: 10.2337/diabetes.47.12.1841. PMID: 9836514.

1: Xu XS, Yan KX, Song H, Lo MW. Quantitative determination of a novel dual PPAR alpha/gamma agonist using on-line turbulent flow extraction with liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jan 5;814(1):29-36. PubMed PMID: 15675045. 2: Miyachi H. [Design and synthesis of subtype- and species-selective peroxisome proliferator-activated receptor (PPAR) alpha ligands]. Yakugaku Zasshi. 2004 Nov;124(11):803-13. Review. Japanese. PubMed PMID: 15516807. 3: Narce M, Poisson JP. Novel PPARgamma-dependent and independent effects for thiazolidinediones. Curr Opin Lipidol. 2003 Dec;14(6):651-2. PubMed PMID: 14624145. 4: Calkin AC, Thomas MC, Cooper ME. MK-767. Kyorin/Banyu/Merck. Curr Opin Investig Drugs. 2003 Apr;4(4):444-8. Review. PubMed PMID: 12808885. 5: Yajima K, Hirose H, Fujita H, Seto Y, Fujita H, Ukeda K, Miyashita K, Kawai T, Yamamoto Y, Ogawa T, Yamada T, Saruta T. Combination therapy with PPARgamma and PPARalpha agonists increases glucose-stimulated insulin secretion in db/db mice. Am J Physiol Endocrinol Metab. 2003 May;284(5):E966-71. Erratum in: Am J Physiol Endocrinol Metab. 2003 Oct;285(4):E926. PubMed PMID: 12676649. 6: Yamanouchi T. [KRP-297, MCC-555]. Nihon Rinsho. 2001 Nov;59(11):2200-6. Review. Japanese. PubMed PMID: 11712408. 7: Murakami K, Ide T, Nakazawa T, Okazaki T, Mochizuki T, Kadowaki T. Fatty-acyl-CoA thioesters inhibit recruitment of steroid receptor co-activator 1 to alpha and gamma isoforms of peroxisome-proliferator-activated receptors by competing with agonists. Biochem J. 2001 Jan 15;353(Pt 2):231-8. PubMed PMID: 11139385; PubMed Central PMCID: PMC1221563. 8: Chaput E, Saladin R, Silvestre M, Edgar AD. Fenofibrate and rosiglitazone lower serum triglycerides with opposing effects on body weight. Biochem Biophys Res Commun. 2000 May 10;271(2):445-50. PubMed PMID: 10799317. 9: Ide T, Nakazawa T, Mochizuki T, Murakami K. Tissue-specific actions of antidiabetic thiazolidinediones on the reduced fatty acid oxidation in skeletal muscle and liver of Zucker diabetic fatty rats. Metabolism. 2000 Apr;49(4):521-5. PubMed PMID: 10778879. 10: Murakami K, Tsunoda M, Ide T, Ohashi M, Mochizuki T. Amelioration by KRP-297, a new thiazolidinedione, of impaired glucose uptake in skeletal muscle from obese insulin-resistant animals. Metabolism. 1999 Nov;48(11):1450-4. PubMed PMID: 10582556. 11: Murakami K, Ide T, Suzuki M, Mochizuki T, Kadowaki T. Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. Biochem Biophys Res Commun. 1999 Jul 14;260(3):609-13. PubMed PMID: 10403814. 12: Nomura M, Kinoshita S, Satoh H, Maeda T, Murakami K, Tsunoda M, Miyachi H, Awano K. (3-substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents. Bioorg Med Chem Lett. 1999 Feb 22;9(4):533-8. PubMed PMID: 10098657. 13: Murakami K, Tobe K, Ide T, Mochizuki T, Ohashi M, Akanuma Y, Yazaki Y, Kadowaki T. A novel insulin sensitizer acts as a coligand for peroxisome proliferator-activated receptor-alpha (PPAR-alpha) and PPAR-gamma: effect of PPAR-alpha activation on abnormal lipid metabolism in liver of Zucker fatty rats. Diabetes. 1998 Dec;47(12):1841-7. PubMed PMID: 9836514.