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

General Information of Drug (ID: DR3076)
Drug Name
GW-501516
Synonyms
317318-70-0; GW501516; GW 501516; Endurobol; GW-501516; GSK-516; UNII-7I2HA1NU22; GW1516; GW 1516; 2-(2-Methyl-4-(((4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)methyl)thio)phenoxy)acetic acid; GW-516; GW-1516; CHEMBL38943; 2-(2-methyl-4-((4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)methylthio)phenoxy)acetic acid; 2-(4-((2-(4-(Trifluoromethyl)phenyl)-4-methylthiazol-5-yl)methylthio)-2-methylphenoxy)acetic acid; 7I2HA1NU22
Indication Diabetes mellitus [ICD11: 5A10] Discontinued in Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 453.5 Topological Polar Surface Area 113
Heavy Atom Count 30 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
9803963
ChEBI ID
CHEBI:73726
CAS Number
317318-70-0
TTD Drug ID
D05HDX
Formula
C21H18F3NO3S2
Canonical SMILES
CC1=C(C=CC(=C1)SCC2=C(N=C(S2)C3=CC=C(C=C3)C(F)(F)F)C)OCC(=O)O
InChI
InChI=1S/C21H18F3NO3S2/c1-12-9-16(7-8-17(12)28-10-19(26)27)29-11-18-13(2)25-20(30-18)14-3-5-15(6-4-14)21(22,23)24/h3-9H,10-11H2,1-2H3,(H,26,27)
InChIKey
YDBLKRPLXZNVNB-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
GW-501516 Metabolite M4 DM016706
143321715
Unclear - Unclear 1 [2]
GW1516-sulfoxide DM016317
71464601
Oxidation - Oxidation 1 [3]
GW-501516 Metabolite M4 DM016706
143321715
Unclear - Unclear 2 [2]
GW1516-sulfone DM016289
68896331
Oxidation - Oxidation 2 [3]
GW-501516 Metabolite M1 DM017889 N. A. Unclear - Unclear 3 [2]
GW-501516 Metabolite M2 DM017886 N. A. Oxidation - Hydroxylation 3 [2]
GW-501516 Metabolite M5 DM017888 N. A. Unclear - Unclear 4 [2]
GW-501516 Metabolite M6 DM015377
2782899
Unclear - Unclear 4 [2]
HMTT DM015378
2783005
Reduction - Reduction 5 [2]
MTTC DM015373
2775663
Oxidation - Carboxylation 5 [2]
GW-501516 Metabolite M3 DM017887 N. A. Conjugation - Glucuronidation 6 [2]
MMTC DM015774
11652360
Oxidation - Methylation 6 [2]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009457 BMS-204352 GW-501516 Metabolite M4 Unclear - Unclear Unclear [2]
MR009446 GW-501516 GW1516-sulfoxide Oxidation - Oxidation Unclear [3]
MR009447 GW1516-sulfoxide GW1516-sulfone Oxidation - Oxidation Unclear [3]
MR009456 GW1516-sulfoxide GW-501516 Metabolite M4 Unclear - Unclear Unclear [2]
MR009448 GW1516-sulfone GW-501516 Metabolite M2 Oxidation - Hydroxylation Unclear [2]
MR009455 GW1516-sulfone GW-501516 Metabolite M1 Unclear - Unclear Unclear [2]
MR009449 GW-501516 Metabolite M2 GW-501516 Metabolite M6 Unclear - Unclear Unclear [2]
MR009454 GW-501516 Metabolite M2 GW-501516 Metabolite M5 Unclear - Unclear Unclear [2]
MR009450 GW-501516 Metabolite M6 MTTC Oxidation - Carboxylation Unclear [2]
MR009452 GW-501516 Metabolite M6 HMTT Reduction - Reduction Unclear [2]
MR009453 HMTT GW-501516 Metabolite M3 Conjugation - Glucuronidation Unclear [2]
MR009451 MTTC MMTC Oxidation - Methylation Unclear [2]
⏷ Show the Full List of 12 MR(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2687).
2 Metabolic study of GW1516 in equine urine using liquid chromatography/electrospray ionization Q-Exactive high-resolution mass spectrometry for doping control
3 Detection of PPAR agonists GW1516 and GW0742 and their metabolites in human urine

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