Muraglitazar
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MedKoo CAT#: 525720

CAS#: 331741-94-7

Description: Muraglitazar is a Peroxime Proliferator Activated (PPAR) Agonist that has glucose- and lipid-lowering activities. It is used for the treatment of Type-2 Diabetes Mellitus, Mixed Dyslipidemia, Atherosclerosis, and Metabolic Syndrome (Dual (alpha and gamma). Muraglitazar improves glycaemic control by enhancing insulin sensitivity and β cell function in T2DM (Type 2 Diabetes Mellitus) subjects, improves multiple cardiovascular risk factors, reduces muscle, visceral and hepatic fat content in T2DM subjects.

Chemical Structure

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Muraglitazar
CAS# 331741-94-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 525720
Name: Muraglitazar
CAS#: 331741-94-7
Chemical Formula: C29H28N2O7
Exact Mass: 516.19
Molecular Weight: 516.542
Elemental Analysis: C, 67.43; H, 5.46; N, 5.42; O, 21.68

Price and Availability

Size Price Availability Quantity
1mg USD 550 2 Weeks
5mg USD 1650 2 Weeks
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Synonym: Pargluva; BMS 298585; BMS-298585; BMS298585; Muraglitazar

IUPAC/Chemical Name: 2-(((4-methoxyphenoxy)carbonyl)(4-(2-(5-methyl-2-phenyloxazol-4-yl)ethoxy)benzyl)amino)acetic acid

InChi Key: IRLWJILLXJGJTD-UHFFFAOYSA-N

InChi Code: InChI=1S/C29H28N2O7/c1-20-26(30-28(37-20)22-6-4-3-5-7-22)16-17-36-24-10-8-21(9-11-24)18-31(19-27(32)33)29(34)38-25-14-12-23(35-2)13-15-25/h3-15H,16-19H2,1-2H3,(H,32,33)

SMILES Code: O=C(O)CN(C(OC1=CC=C(OC)C=C1)=O)CC2=CC=C(OCCC3=C(C)OC(C4=CC=CC=C4)=N3)C=C2

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

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Muraglitazar is a PPAR α/γ dual agonist for the treatment of type 2 diabetes and associated dyslipidemia.
In vitro activity: In this study, the effects of various PPAR agonists, i.e. fenofibrate, bezafibrate, troglitazone, rosiglitazone, muraglitazar and tesaglitazar on oleic acid-induced steatotic HepaRG cells were investigated after a single 24-hour or 2-week repeat treatment. The greatest effects on reduction of steatosis were obtained with the dual PPARα/γ agonist muraglitazar. Reference: Toxicol Appl Pharmacol. 2014 Apr 1;276(1):73-81. https://pubmed.ncbi.nlm.nih.gov/24534255/
In vivo activity: In study 2, diabetic db/db mice were treated for 4 weeks. The control mice displayed increased glucose levels, severe loss of islets, and their isolated islets secreted reduced amounts of insulin in response to glucose and exendin-4 compared with baseline. In muraglitazar-treated mice, glucose levels were reduced to normal. These mice showed reduced loss of islets, and their isolated islets secreted insulin at levels comparable to baseline. Thus, muraglitazar treatment decreased both insulin resistance and preserved beta-cell function. Reference: J Pharmacol Exp Ther. 2007 Apr;321(1):107-15. https://pubmed.ncbi.nlm.nih.gov/17259449/

Preparing Stock Solutions

The following data is based on the product molecular weight 516.54 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
Formulation protocol: 1. Rogue A, Anthérieu S, Vluggens A, Umbdenstock T, Claude N, de la Moureyre-Spire C, Weaver RJ, Guillouzo A. PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells. Toxicol Appl Pharmacol. 2014 Apr 1;276(1):73-81. doi: 10.1016/j.taap.2014.02.001. Epub 2014 Feb 15. PMID: 24534255. 2. Devasthale PV, Chen S, Jeon Y, Qu F, Shao C, Wang W, Zhang H, Cap M, Farrelly D, Golla R, Grover G, Harrity T, Ma Z, Moore L, Ren J, Seethala R, Cheng L, Sleph P, Sun W, Tieman A, Wetterau JR, Doweyko A, Chandrasena G, Chang SY, Humphreys WG, Sasseville VG, Biller SA, Ryono DE, Selan F, Hariharan N, Cheng PT. Design and synthesis of N-[(4-methoxyphenoxy)carbonyl]-N-[[4-[2-(5- methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]glycine [Muraglitazar/BMS-298585], a novel peroxisome proliferator-activated receptor alpha/gamma dual agonist with efficacious glucose and lipid-lowering activities. J Med Chem. 2005 Mar 24;48(6):2248-50. doi: 0.1021/jm0496436. PMID: 15771468. 3. Paukkeri EL, Leppänen T, Lindholm M, Yam MF, Asmawi MZ, Kolmonen A, Aulaskari PH, Moilanen E. Anti-inflammatory properties of a dual PPARgamma/alpha agonist muraglitazar in in vitro and in vivo models. Arthritis Res Ther. 2013 Apr 17;15(2):R51. doi: 10.1186/ar4211. PMID: 23594962; PMCID: PMC4060226. 4. Tozzo E, Ponticiello R, Swartz J, Farrelly D, Zebo R, Welzel G, Egan D, Kunselman L, Peters A, Gu L, French M, Chen S, Devasthale P, Janovitz E, Staal A, Harrity T, Belder R, Cheng PT, Whaley J, Taylor S, Hariharan N. The dual peroxisome proliferator-activated receptor alpha/gamma activator muraglitazar prevents the natural progression of diabetes in db/db mice. J Pharmacol Exp Ther. 2007 Apr;321(1):107-15. doi: 10.1124/jpet.106.115337. Epub 2007 Jan 26. PMID: 17259449.
In vitro protocol: 1. Rogue A, Anthérieu S, Vluggens A, Umbdenstock T, Claude N, de la Moureyre-Spire C, Weaver RJ, Guillouzo A. PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells. Toxicol Appl Pharmacol. 2014 Apr 1;276(1):73-81. doi: 10.1016/j.taap.2014.02.001. Epub 2014 Feb 15. PMID: 24534255. 2. Devasthale PV, Chen S, Jeon Y, Qu F, Shao C, Wang W, Zhang H, Cap M, Farrelly D, Golla R, Grover G, Harrity T, Ma Z, Moore L, Ren J, Seethala R, Cheng L, Sleph P, Sun W, Tieman A, Wetterau JR, Doweyko A, Chandrasena G, Chang SY, Humphreys WG, Sasseville VG, Biller SA, Ryono DE, Selan F, Hariharan N, Cheng PT. Design and synthesis of N-[(4-methoxyphenoxy)carbonyl]-N-[[4-[2-(5- methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]glycine [Muraglitazar/BMS-298585], a novel peroxisome proliferator-activated receptor alpha/gamma dual agonist with efficacious glucose and lipid-lowering activities. J Med Chem. 2005 Mar 24;48(6):2248-50. doi: 10.1021/jm0496436. PMID: 15771468.
In vivo protocol: 1. Paukkeri EL, Leppänen T, Lindholm M, Yam MF, Asmawi MZ, Kolmonen A, Aulaskari PH, Moilanen E. Anti-inflammatory properties of a dual PPARgamma/alpha agonist muraglitazar in in vitro and in vivo models. Arthritis Res Ther. 2013 Apr 17;15(2):R51. doi: 10.1186/ar4211. PMID: 23594962; PMCID: PMC4060226. 2. Tozzo E, Ponticiello R, Swartz J, Farrelly D, Zebo R, Welzel G, Egan D, Kunselman L, Peters A, Gu L, French M, Chen S, Devasthale P, Janovitz E, Staal A, Harrity T, Belder R, Cheng PT, Whaley J, Taylor S, Hariharan N. The dual peroxisome proliferator-activated receptor alpha/gamma activator muraglitazar prevents the natural progression of diabetes in db/db mice. J Pharmacol Exp Ther. 2007 Apr;321(1):107-15. doi: 10.1124/jpet.106.115337. Epub 2007 Jan 26. PMID: 17259449.

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1: Coletta DK, Fernandez M, Cersosimo E, Gastaldelli A, Musi N, DeFronzo RA. The effect of muraglitazar on adiponectin signalling, mitochondrial function and fat oxidation genes in human skeletal muscle in vivo. Diabet Med. 2015 May;32(5):657-64. doi: 10.1111/dme.12664. Epub 2015 Jan 7. PubMed PMID: 25484175.

2: Paukkeri EL, Leppänen T, Lindholm M, Yam MF, Asmawi MZ, Kolmonen A, Aulaskari PH, Moilanen E. Anti-inflammatory properties of a dual PPARgamma/alpha agonist muraglitazar in in vitro and in vivo models. Arthritis Res Ther. 2013 Apr 17;15(2):R51. doi: 10.1186/ar4211. PubMed PMID: 23594962; PubMed Central PMCID: PMC4060226.

3: Fernandez M, Gastaldelli A, Triplitt C, Hardies J, Casolaro A, Petz R, Tantiwong P, Musi N, Cersosimo E, Ferrannini E, DeFronzo RA. Metabolic effects of muraglitazar in type 2 diabetic subjects. Diabetes Obes Metab. 2011 Oct;13(10):893-902. doi: 10.1111/j.1463-1326.2011.01429.x. PubMed PMID: 21615671.