MURAGLITAZAR

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

Structure Search

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)

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20368213 | https://www.ncbi.nlm.nih.gov/pubmed/15771468

Muraglitazar previously known as BMS-298585 has been identified as a non-thiazolidinedione dual agonist of peroxisome proliferator-activated receptor alpha/gamma. Muraglitazar is currently in clinical trial phase III development for the treatment of type 2 diabetes and dyslipidemia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771468	Agonist 2678		320.0 nM [EC50]
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771468	Agonist 2678		110.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://clinicaltrials.gov/ct2/show/NCT00240383	Primary		Phase III 656	Unknown Approved Use Unknown
Dyslipidemia 30 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16341289	Primary		Phase III 656	Unknown Approved Use Unknown

C_max

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

T_1/2

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

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P007HMK	https://www.1pchem.com/search?query=1P007HMK
Angene	AGN-PC-04XYUX	http://www.angenechemical.com/productshow/AGN-PC-04XYUX.html
ApexBio Technology	C3986	https://www.apexbt.com/catalogsearch/result/?q=C3986
Cayman Chemical	10007853	http://www.caymanchem.com/app/template/Product.vm/catalog/10007853
MolPort	MolPort-006-395-259	https://www.molport.com/shop/molecule-link/MolPort-006-395-259
MuseChem	R009405	https://www.musechem.com/product/R009405.html
Toronto Research Chemicals	M796500	https://www.trc-canada.com/product-detail/?CatNum=M796500
Toronto Research Chemicals	S687350	https://www.trc-canada.com/product-detail/?CatNum=S687350
Wonderchem	WD05WNG	http://www.wonder-chem.com/search.html?text=WD05WNG
eMolecules	10595085	https://orderbb.emolecules.com/search/#?query=10595085
mcule	MCULE-5270352456	https://mcule.com/MCULE-5270352456/

PubMed

Title	Date	PubMed
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	16104078
One pill, two conditions.	2005 Oct	16299847
Dual and pan-peroxisome proliferator-activated receptors (PPAR) co-agonism: the bezafibrate lessons.	2005 Sep 16	16168052
Is it safe to combine PPAR agonists? A lesson from muraglitazar.	2006	16762511
Pharmacokinetics of muraglitazar (BMS-298585), a dual peroxisome proliferator-activated receptors (PPAR) alpha and gamma activator, in mice, rats, dogs, and monkeys.	2006 Dec	17162469
PPARalpha and PPARgamma dual agonists for the treatment of type 2 diabetes and the metabolic syndrome.	2006 Dec	16973418
Gateways to clinical trials.	2006 Jun	16845450
[Dipeptidylpeptidase IV inhibitors and dual action PPAR-agonists].	2006 Mar	16550882
Adverse events related to muraglitazar use in diabetes.	2006 May 3	16670404
Characterization of the UDP glucuronosyltransferase activity of human liver microsomes genotyped for the UGT1A1*28 polymorphism.	2007 Dec	17898154
Subchronic urinary bladder effects of muraglitazar in male rats.	2007 Mar	17132713
PPARgamma in Kidney Physiology and Pathophysiology.	2008	19283081
Optimization to eliminate the interference of migration isomers for measuring 1-O-beta-acyl glucuronide without extensive chromatographic separation.	2008	18059002
Design, synthesis, and biological evaluation of novel constrained meta-substituted phenyl propanoic acids as peroxisome proliferator-activated receptor alpha and gamma dual agonists.	2008 Oct 23	18826205
Coadministration of muraglitazar plus glyburide: improvement of glycaemic and lipid profiles in patients with type 2 diabetes.	2009 Apr	20368202
PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells.	2014 Apr 1	24534255

Patents

Sample Use Guides

In Vivo Use Guide

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

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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:53:05 GMT 2023` Edited by `admin` on `Fri Dec 15 15:53:05 GMT 2023`
Record UNII	W1MKM70WQI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MURAGLITAZAR

Official Name

English

MURAGLITAZAR [USAN]

Common Name

English

BMS-298585

Code

English

MURAGLITAZAR [MART.]

Common Name

English

muraglitazar [INN]

Common Name

English

[[(4-Methoxyphenoxy)carbonyl][4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]benzyl]amino]acetic acid

Systematic Name

English

BMS-298585-01

Code

English

N-((4-METHOXYPHENOXY)CARBONYL)-N-((4-(2-(5-METHYL-2-PHENYL-4-OXAZOLYL)ETHOXY)PHENYL)-METHYL)GLYCINE

Systematic Name

English

MURAGLITAZAR [MI]

Common Name

English

GLYCINE, N-((4-METHOXYPHENOXY)CARBONYL)-N-((4-(2-(5-METHYL-2-PHENYL-4-OXAZOLYL)ETHOXY)PHENYL)METHYL)-

Systematic Name

English

Muraglitazar [WHO-DD]

Common Name

English

MK-0478

Code

English

MK0478

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C98233