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)
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771468
Curator's Comment: # Bristol-Myers Squibb Pharmaceutical Research Institute
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771468 |
320.0 nM [EC50] | ||
Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771468 |
110.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
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Gateways to clinical trials. | 2004 Sep |
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Muraglitazar (Bristol-Myers Squibb/Merck). | 2005 Apr |
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Muraglitazar, a dual (alpha/gamma) PPAR activator: a randomized, double-blind, placebo-controlled, 24-week monotherapy trial in adult patients with type 2 diabetes. | 2005 Aug |
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Meeting highlights. 65th annual scientific sessions of the American Diabetes Association, San Diego. Dual PPAR agonist improves glycemic control, lipids in type 2 diabetes. | 2005 Aug |
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American Diabetes Association - 65th Scientific Sessions. PPAR agents. | 2005 Aug |
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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. | 2005 Mar 24 |
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Molecule of the month. Muraglitazar. | 2005 May |
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Selling safety--lessons from muraglitazar. | 2005 Nov 23 |
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K-111: the emerging evidence for its potential in the treatment of the metabolic syndrome. | 2006 |
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A bumpy road to breakthroughs. The news: it's hard to beat today's cardiac treatments. | 2006 Feb |
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A 96-well single-pot protein precipitation, liquid chromatography/tandem mass spectrometry (LC/MS/MS) method for the determination of muraglitazar, a novel diabetes drug, in human plasma. | 2006 Feb 2 |
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Gateways to clinical trials. | 2006 Jun |
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[Dipeptidylpeptidase IV inhibitors and dual action PPAR-agonists]. | 2006 Mar |
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Drug safety system needs overhaul, experts say. | 2006 Mar 15 |
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Adverse events related to muraglitazar use in diabetes. | 2006 May 3 |
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Treatment update: thiazolidinediones in combination with metformin for the treatment of type 2 diabetes. | 2007 |
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The dual peroxisome proliferator-activated receptor alpha/gamma activator muraglitazar prevents the natural progression of diabetes in db/db mice. | 2007 Apr |
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Subchronic urinary bladder effects of muraglitazar in male rats. | 2007 Mar |
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The integration of lipid-sensing and anti-inflammatory effects: how the PPARs play a role in metabolic balance. | 2007 May 25 |
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Urine acidification has no effect on peroxisome proliferator-activated receptor (PPAR) signaling or epidermal growth factor (EGF) expression in rat urinary bladder urothelium. | 2007 Sep 15 |
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The Development of INT131 as a Selective PPARgamma Modulator: Approach to a Safer Insulin Sensitizer. | 2008 |
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Peroxisome Proliferators-Activated Receptor (PPAR) Modulators and Metabolic Disorders. | 2008 |
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Genetic and gene expression studies implicate renin and endothelin-1 in edema caused by peroxisome proliferator-activated receptor gamma agonists. | 2008 Oct |
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PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells. | 2014 Apr 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16199244
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771468
Muraglitazar/BMS-298585 (2) has been identified as a non-thiazolidinedione PPAR alpha/gamma dual agonist that shows potent activity in vitro at human PPARalpha (EC(50) = 320 nM) and PPARgamma(EC(50) = 110 nM).
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C98233
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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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ACTIVE MOIETY
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