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Compound Detail

CHEMBL186179

MURAGLITAZAR
🧪 Phase III
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🧪 Phase III
COc1ccc(OC(=O)N(CC(=O)O)Cc2ccc(OCCc3nc(-c4ccccc4)oc3C)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL186179
Name MURAGLITAZAR
Phase Phase III
Structure Type MOL
InChI Key IRLWJILLXJGJTD-UHFFFAOYSA-N

Known Names

BMS-298585 BMS-298585-01 MK-0478 MK0478 Muraglitazar
3
Targets
27
Activities
2
Assay Types
28
PK Parameters
20
Publications
5
Known Names
3
Indications
2
Mechanisms

Molecular Properties

516.5
MW (Da)
5.37
ALogP
7
HBA
1
HBD
111.3
PSA (Ų)
0.28
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -glitazar
USAN Year 2003

Extended Properties

Molecular Formula C29H28N2O7
MW 516.55
Aromatic Rings 4
Heavy Atoms 38
NP-Likeness -0.96

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Peroxisome proliferator-activated receptor alpha agonist AGONIST Peroxisome proliferator-activated receptor alpha ✓ ✓
Peroxisome proliferator-activated receptor gamma agonist AGONIST Peroxisome proliferator-activated receptor gamma ✓ ✓

Indications

Diabetes Mellitus Diabetes Mellitus, Type 2 Lipid Metabolism Disorders

Activity Summary

EC50 20 meas. best 8.52
IC50 7 meas. best 6.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 EC50 8.52 7.339 3.0 10
Peroxisome proliferator-activated receptor alpha
CHEMBL239
 EC50 7.3 6.292 50.0 10
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 IC50 6.92 6.7467 120.0 3
Peroxisome proliferator-activated receptor alpha
CHEMBL239
 IC50 6.72 6.66 190.0 2
Unchecked
CHEMBL612545
 IC50 5.81 5.125 1535.1 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 49000.0 ng.hr.mL-1 Mus musculus
AUC 27700.0 ng.hr.mL-1 Mus musculus
AUC 105000.0 ng.hr.mL-1 Rattus norvegicus
AUC 1100.0 ng.hr.mL-1 Canis lupus familiaris
AUC 71000.0 ng.hr.mL-1 Macaca fascicularis
AUC 9000.0 ng.hr.mL-1 Homo sapiens
AUC 52171.55 ng.hr.mL-1 Rattus norvegicus
AUC 51035.14 ng.hr.mL-1 Rattus norvegicus
CL 3.0 mL.min-1.kg-1 Mus musculus
CL 0.73 mL.min-1.kg-1 Rattus norvegicus
Cmax 20.8 μg/mL Mus musculus
Cmax 26134.93 nM Rattus norvegicus
Cmax 1935.92 nM Canis lupus familiaris
Cmax 13745.04 nM Macaca fascicularis
Cmax 2710.29 nM Homo sapiens
Cmax 25800.0 nM Rattus norvegicus
F 96.2 % Rattus norvegicus
T1/2 7.3 hr Mus musculus
T1/2 3.8 hr Rattus norvegicus
T1/2 23.5 hr Macaca fascicularis
T1/2 19.8 hr Homo sapiens
T1/2 14.0 hr Rattus norvegicus
Tmax 0.4 hr Mus musculus
Tmax 0.5 hr Rattus norvegicus
Tmax 1.0 hr Canis lupus familiaris
Tmax 1.0 hr Macaca fascicularis
Tmax 1.0 hr Homo sapiens
Tmax 0.58 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Peroxisome proliferator-activated receptor gamma EC50 = 3.0 nM 8.52 Transactivation of human Gal4-fused PPARgamma LBD expressed in African green mon... 28609708
Peroxisome proliferator-activated receptor gamma EC50 = 16.0 nM 7.8 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Peroxisome proliferator-activated receptor gamma EC50 = 35.0 nM 7.46 Binding affinity to PPARgamma by fluorescence polarization assay 19201606
Peroxisome proliferator-activated receptor gamma EC50 = 35.0 nM 7.46 Agonist activity at GAL4 tagged human PPARgamma ligand binding domain expressed ... 25686852
Peroxisome proliferator-activated receptor gamma EC50 = 40.0 nM 7.4 Agonist activity at human PPARgamma expressed in HEK293 cells assessed as lucife... 18511276
Peroxisome proliferator-activated receptor alpha EC50 = 50.0 nM 7.3 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Peroxisome proliferator-activated receptor gamma EC50 = 90.0 nM 7.05 Agonist activity at human PPARgamma transactivation expressed in human HePG2 cel... 18976908
Peroxisome proliferator-activated receptor gamma EC50 = 100.0 nM 7.0 Agonist activity at GAL4-fused PPARgamma assessed as transcriptional activity by... 23084275
Peroxisome proliferator-activated receptor gamma EC50 = 110.0 nM 6.96 Effective concentration against human Peroxisome proliferator activated receptor... 15771468
Peroxisome proliferator-activated receptor gamma IC50 = 120.0 nM 6.92 Competitive displacement of fluorescently labelled PPAR tracer ligand from GST-t... 30429097
Peroxisome proliferator-activated receptor gamma EC50 = 120.0 nM 6.92 Effective concentration against human peroxisome proliferator activated receptor... 15293980
Peroxisome proliferator-activated receptor gamma EC50 = 153.0 nM 6.82 Agonist activity at human PPARgamma expressed in african green monkey CV-1 co-tr... 18771917
Peroxisome proliferator-activated receptor alpha EC50 = 150.0 nM 6.82 Agonist activity at human PPARalpha transactivation expressed in human HePG2 cel... 18976908
Peroxisome proliferator-activated receptor alpha IC50 = 190.0 nM 6.72 Binding affinity at human PPARalpha by fluorescence polarization 18511276
Peroxisome proliferator-activated receptor gamma IC50 = 190.0 nM 6.72 Inhibition of human Peroxisome proliferator activated receptor gamma 15771468
Peroxisome proliferator-activated receptor alpha EC50 = 240.0 nM 6.62 Effective concentration against human peroxisome proliferator activated receptor... 15293980
Peroxisome proliferator-activated receptor gamma IC50 = 250.0 nM 6.6 Binding affinity at human PPARalpha by fluorescence polarization 18511276
Peroxisome proliferator-activated receptor alpha IC50 = 250.0 nM 6.6 Inhibition of human Peroxisome proliferator activated receptor alpha 15771468
Peroxisome proliferator-activated receptor alpha EC50 = 300.0 nM 6.52 Agonist activity at GAL4-fused PPARalpha assessed as transcriptional activity by... 23084275
Peroxisome proliferator-activated receptor alpha EC50 = 320.0 nM 6.5 Effective concentration against human Peroxisome proliferator activated receptor... 15771468

Literature References

PubMed DOI Target Context # Activities
17062777 10.1124/dmd.106.012450 ADMET 141
17062777 10.1124/dmd.106.012450 Plasma 74
17062777 10.1124/dmd.106.012450 Hepatocyte 40
17062777 10.1124/dmd.106.012450 Rattus norvegicus 35
15771468 10.1021/jm0496436 Mus musculus 11
18771917 10.1016/j.bmcl.2008.08.020 Mus musculus 9
17062777 10.1124/dmd.106.012450 Cynomolgus monkey 8
18771917 10.1016/j.bmcl.2008.08.020 Rattus norvegicus 8
- 10.6019/CHEMBL5303304 HEK-293T 7
- 10.6019/CHEMBL5303304 Fibroblast 7
17062777 10.1124/dmd.106.012450 Homo sapiens 6
18826205 10.1021/jm8003416 Mus musculus 6
- 10.6019/CHEMBL5303304 U2OS 5
17062777 10.1124/dmd.106.012450 Canis familiaris 5
- 10.6019/CHEMBL5724696 TERT-RPE1 4
28609708 10.1016/j.ejmech.2017.06.006 Mus musculus 4
17292606 10.1016/j.bmcl.2007.01.060 Mus musculus 4
29446942 10.1021/acs.jmedchem.7b01285 Rattus norvegicus 3
18511276 10.1016/j.bmcl.2008.05.014 Peroxisome proliferator-activated receptor gamma 3
18511276 10.1016/j.bmcl.2008.05.014 Peroxisome proliferator-activated receptor alpha 3

Data from ChEMBL 36 via Core Engine