Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C29H28N2O7 |
| Molecular Weight | 516.5418 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(OC(=O)N(CC(O)=O)CC2=CC=C(OCCC3=C(C)OC(=N3)C4=CC=CC=C4)C=C2)C=C1
InChI
InChIKey=IRLWJILLXJGJTD-UHFFFAOYSA-N
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)
| Molecular Formula | C29H28N2O7 |
| Molecular Weight | 516.5418 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17062777 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
MURAGLITAZAR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
12 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17062777 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
MURAGLITAZAR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
35.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17062777 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
MURAGLITAZAR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells. | 2014-04-01 |
|
| Comparative gene expression profiles induced by PPARγ and PPARα/γ agonists in rat hepatocytes. | 2011-07-01 |
|
| Successful drug development despite adverse preclinical findings part 2: examples. | 2010-12 |
|
| A PPARα promoter variant impairs ERR-dependent transactivation and decreases mortality after acute coronary ischemia in patients with diabetes. | 2010-09-03 |
|
| Synthesis and structure-activity relationships of 2-aryl-4-oxazolylmethoxy benzylglycines and 2-aryl-4-thiazolylmethoxy benzylglycines as novel, potent PPARalpha selective activators- PPARalpha and PPARgamma selectivity modulation. | 2010-05-01 |
|
| Effects of pioglitazone, a peroxisome proliferator-activated receptor gamma agonist, on the urine and urothelium of the rat. | 2010-02 |
|
| Gene Expression Changes Induced by PPAR Gamma Agonists in Animal and Human Liver. | 2010 |
|
| Peroxisome proliferator-activated receptor (PPAR): balance for survival in parasitic infections. | 2010 |
|
| Improving access to FDA reviews and documents. | 2009-11-25 |
|
| A cardiologic approach to non-insulin antidiabetic pharmacotherapy in patients with heart disease. | 2009-07-20 |
|
| PPAR-alpha and PPAR-gamma agonists for type 2 diabetes. | 2009-07-11 |
|
| Efficacy and safety of muraglitazar: a double-blind, 24-week, dose-ranging study in patients with type 2 diabetes. | 2009-07 |
|
| Coadministration of muraglitazar plus glyburide: improvement of glycaemic and lipid profiles in patients with type 2 diabetes. | 2009-04 |
|
| Effects of chronic PPAR-agonist treatment on cardiac structure and function, blood pressure, and kidney in healthy sprague-dawley rats. | 2009 |
|
| Modulation of PPAR receptor subtype selectivity of the ligands: aliphatic chain vs aromatic ring as a spacer between pharmacophore and the lipophilic moiety. | 2008-12-15 |
|
| Design, synthesis, and biological evaluation of novel constrained meta-substituted phenyl propanoic acids as peroxisome proliferator-activated receptor alpha and gamma dual agonists. | 2008-10-23 |
|
| Genetic and gene expression studies implicate renin and endothelin-1 in edema caused by peroxisome proliferator-activated receptor gamma agonists. | 2008-10 |
|
| Improvement of glycaemic and lipid profiles with muraglitazar plus metformin in patients with type 2 diabetes: an active-control trial with glimepiride. | 2008-09 |
|
| Therapy for nonalcoholic fatty liver disease. | 2008-04 |
|
| Rapid and sensitive characterization of the metabolite formation enzyme kinetics of radiolabeled drugs using stop-flow liquid radiochromatography. | 2008-01 |
|
| Development of Synthetic Modulators of PPARs: Current Challenges and Future Opportunities. | 2008 |
|
| PPARgamma in Kidney Physiology and Pathophysiology. | 2008 |
|
| Rat Urinary Bladder Carcinogenesis by Dual-Acting PPARalpha + gamma Agonists. | 2008 |
|
| Renal and vascular mechanisms of thiazolidinedione-induced fluid retention. | 2008 |
|
| The Development of INT131 as a Selective PPARgamma Modulator: Approach to a Safer Insulin Sensitizer. | 2008 |
|
| Peroxisome Proliferators-Activated Receptor (PPAR) Modulators and Metabolic Disorders. | 2008 |
|
| PPAR-gamma, Microglial Cells, and Ocular Inflammation: New Venues for Potential Therapeutic Approaches. | 2008 |
|
| Should We Use PPAR Agonists to Reduce Cardiovascular Risk? | 2008 |
|
| PPAR Agonists and Cardiovascular Disease in Diabetes. | 2008 |
|
| Optimization to eliminate the interference of migration isomers for measuring 1-O-beta-acyl glucuronide without extensive chromatographic separation. | 2008 |
|
| Mass defect filtering on high resolution LC/MS data as a methodology for detecting metabolites with unpredictable structures: identification of oxazole-ring opened metabolites of muraglitazar. | 2007-12 |
|
| Accessing FDA approval packages and briefing documents. | 2007-12 |
|
| Characterization of the UDP glucuronosyltransferase activity of human liver microsomes genotyped for the UGT1A1*28 polymorphism. | 2007-12 |
|
| Nonclinical safety evaluation of muraglitazar, a novel PPARalpha/gamma agonist. | 2007-11 |
|
| Urine acidification has no effect on peroxisome proliferator-activated receptor (PPAR) signaling or epidermal growth factor (EGF) expression in rat urinary bladder urothelium. | 2007-09-15 |
|
| PPAR dual agonists: are they opening Pandora's Box? | 2007-08 |
|
| Design, synthesis, and structure-activity relationship of carbamate-tethered aryl propanoic acids as novel PPARalpha/gamma dual agonists. | 2007-07-01 |
|
| Rodent carcinogenicity profile of the antidiabetic dual PPAR alpha and gamma agonist muraglitazar. | 2007-07 |
|
| The integration of lipid-sensing and anti-inflammatory effects: how the PPARs play a role in metabolic balance. | 2007-05-25 |
|
| The dual peroxisome proliferator-activated receptor alpha/gamma activator muraglitazar prevents the natural progression of diabetes in db/db mice. | 2007-04 |
|
| Subchronic urinary bladder effects of muraglitazar in male rats. | 2007-03 |
|
| Increase in weight induced by muraglitazar, a dual PPARalpha/gamma agonist, in db/db mice: adipogenesis/or oedema? | 2007-02 |
|
| Assessment of dose proportionality of muraglitazar after repeated oral dosing in rats via a sparse sampling methodology. | 2007-01 |
|
| Involvement of multiple cytochrome P450 and UDP-glucuronosyltransferase enzymes in the in vitro metabolism of muraglitazar. | 2007-01 |
|
| Comparative metabolism of radiolabeled muraglitazar in animals and humans by quantitative and qualitative metabolite profiling. | 2007-01 |
|
| Treatment update: thiazolidinediones in combination with metformin for the treatment of type 2 diabetes. | 2007 |
|
| Pharmacokinetics of muraglitazar (BMS-298585), a dual peroxisome proliferator-activated receptors (PPAR) alpha and gamma activator, in mice, rats, dogs, and monkeys. | 2006-12 |
|
| A bumpy road to breakthroughs. The news: it's hard to beat today's cardiac treatments. | 2006-02 |
|
| K-111: the emerging evidence for its potential in the treatment of the metabolic syndrome. | 2006 |
|
| Urothelial carcinogenesis in the urinary bladder of male rats treated with muraglitazar, a PPAR alpha/gamma agonist: Evidence for urolithiasis as the inciting event in the mode of action. | 2006 |
Sample Use Guides
This was a randomized, double-blind, placebo-controlled, parallel-group, multicenter, 24-week monotherapy study in drug-naive, type 2 diabetes patients with inadequate glycemic control. Men and women aged 18 to 70 years with a body mass index < or =41 kg/m(2) and serum triglyceride levels < or =600 mg/dL were eligible for study participation. The study included double-blind and open-label treatment phases. Patients with glycosylated hemoglobin (HbA(1c)) levels > or =7.0% and < or =10.0% at screening were enrolled in the double-blind treatment phase. These patients received treatment with muraglitazar 2.5 mg, muraglitazar 5 mg, or placebo.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:12:03 GMT 2025
by
admin
on
Mon Mar 31 18:12:03 GMT 2025
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| Record UNII |
W1MKM70WQI
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C98233
Created by
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| Code System | Code | Type | Description | ||
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SUB21507
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W1MKM70WQI
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CHEMBL186179
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8442
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PP-02
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MURAGLITAZAR
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331741-94-7
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DB06510
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100000088312
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DTXSID9057719
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206044
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m1210
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C75190
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C500085
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EXCRETED UNCHANGED |
FECAL
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TARGET -> AGONIST |
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EXCRETED UNCHANGED |
URINE
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TARGET -> AGONIST |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
PLASMA, BILE
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
BILE
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
TRACE AMOUNT
PLASMA
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
URINE, BILE
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
at 4h
TRACE AMOUNT
PLASMA
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METABOLITE -> PARENT |
FECAL
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
|---|---|---|---|---|---|---|
| Biological Half-life | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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| Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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