Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1117)
Drug Name
BMS-298585
Synonyms
Muraglitazar; Muraglitazar (USAN/INN); Muraglitazar [USAN:INN]; Pargluva; SCHEMBL676469; Tox21_113946; W1MKM70WQI; 331741-94-7; AC1L4FVP; BMS 298585; BMS-298585; BMS298585; CCRIS 9258; CHEMBL186179; CTK8E8901; DSSTox_CID_31508; DSSTox_GSID_57719; DSSTox_RID_97393; DTXSID9057719; N-((4-methoxyphenoxy)carbonyl)-N-((4-(2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy)phenyl)methyl)glycine; IRLWJILLXJGJTD-UHFFFAOYSA-N; N-[(4-Methoxyphenoxy)carbonyl]-N-[[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]glycine; UNII-W1MKM70WQI
Indication Diabetes mellitus [ICD11: 5A10] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 516.5 Topological Polar Surface Area 111
Heavy Atom Count 38 Rotatable Bond Count 12
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
206044
CAS Number
331741-94-7
TTD Drug ID
D0M3UT
Formula
C29H28N2O7
Canonical SMILES
CC1=C(N=C(O1)C2=CC=CC=C2)CCOC3=CC=C(C=C3)CN(CC(=O)O)C(=O)OC4=CC=C(C=C4)OC
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)
InChIKey
IRLWJILLXJGJTD-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
BMS-298585 metabolite M1 DM002483
44448487
Oxidation - O-Dealkylation 1 [2] , [4]
BMS-298585 metabolite M10 DM002488
44448403
Unclear 1 [2] , [4]
BMS-298585 metabolite M11 DM002489
136036579
Unclear 1 [2] , [4]
BMS-298585 metabolite M13 DM002490
101838878
Unclear 1 [2] , [4]
BMS-298585 metabolite M14 DM002487
44448594
Unclear 1 [2] , [4]
BMS-298585 metabolite M15 DM002486
44448345
Unclear 1 [2] , [4]
BMS-298585 metabolite M16 DM002485
44448593
Unclear 1 [2] , [4]
BMS-298585 metabolite M9 DM002484
44448632
Unclear 1 [2] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000376 BMS-298585 BMS-298585 metabolite M1 Oxidation - O-Dealkylation CYP3A4 ... [2], [4]
MR000377 BMS-298585 BMS-298585 metabolite M9 Unclear Unclear [2], [4]
MR000378 BMS-298585 BMS-298585 metabolite M16 Unclear CYP3A4 ... [2], [4]
MR000379 BMS-298585 BMS-298585 metabolite M15 Unclear CYP2C8 ... [2], [4]
MR000380 BMS-298585 BMS-298585 metabolite M14 Unclear CYP3A4 [2], [4]
MR000381 BMS-298585 BMS-298585 metabolite M10 Unclear CYP3A4 ... [2], [4]
MR000382 BMS-298585 BMS-298585 metabolite M11 Unclear CYP2C19 [2], [4]
MR000383 BMS-298585 BMS-298585 metabolite M13 Unclear UGT1A9 ... [2], [4]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
⏷ Show the Full List of 8  DME(s)
References
1 ClinicalTrials.gov (NCT00094991) Mechanism of Action and Efficacy of Muraglitazar in Type 2 Diabetes.
2 Involvement of multiple cytochrome P450 and UDP-glucuronosyltransferase enzymes in the in vitro metabolism of muraglitazar. Drug Metab Dispos. 2007 Jan;35(1):139-49.
3 Characterization of the UDP glucuronosyltransferase activity of human liver microsomes genotyped for the UGT1A1*28 polymorphism. Drug Metab Dispos. 2007 Dec;35(12):2270-80.
4 Glucuronidation as a major metabolic clearance pathway of 14c-labeled muraglitazar in humans: metabolic profiles in subjects with or without bile collection Drug Metab Dispos. 2006 Mar;34(3):427-39. doi: 10.1124/dmd.105.007617.

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