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

General Information of Drug (ID: DR3399)
Drug Name
FG-4592
Synonyms
FG-4592; 808118-40-3; Roxadustat; Roxadustat (FG-4592); UNII-X3O30D9YMX; N-[(4-Hydroxy-1-methyl-7-phenoxy-3-isoquinolinyl)carbonyl]glycine; FG4592; ASP1517; Glycine, N-[(4-hydroxy-1-methyl-7-phenoxy-3-isoquinolinyl)carbonyl]-; X3O30D9YMX; CHEMBL2338329; 2-[(4-hydroxy-1-methyl-7-phenoxyisoquinoline-3-carbonyl)amino]acetic acid; FG 4592; AK198953; n-((4-hydroxy-1-methyl-7-phenoxy-3-isoquinolinyl)carbonyl)glycine; [[(4-Hydroxy-1-methyl-7-phenoxyisoquinolin-3-yl)carbonyl]amino]acetic Acid
Indication Anaemia [ICD11: 3A90] Phase 3 [1]
Kidney disease [ICD11: ICD11: GC2Z] Phase 3 [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 352.3 Topological Polar Surface Area 109
Heavy Atom Count 26 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
11256664
ChEBI ID
CHEBI:132774
CAS Number
808118-40-3
TTD Drug ID
D03YKE
Formula
C19H16N2O5
Canonical SMILES
CC1=C2C=C(C=CC2=C(C(=N1)C(=O)NCC(=O)O)O)OC3=CC=CC=C3
InChI
InChI=1S/C19H16N2O5/c1-11-15-9-13(26-12-5-3-2-4-6-12)7-8-14(15)18(24)17(21-11)19(25)20-10-16(22)23/h2-9,24H,10H2,1H3,(H,20,25)(H,22,23)
InChIKey
YOZBGTLTNGAVFU-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
FG-4592 Metabolites M1-M3 DM019461 N. A. Oxidation - Hydroxylation 1 [4]
FG-4592 Metabolites M4 DM019469 N. A. Unclear - Unclear 1 [4]
FG-4592 Metabolites M5 DM016188
57469177
Oxidation - Dealkylation 1 [4]
FG-4592 Metabolites M8 DM019467 N. A. Conjugation - Glucuronidation 1 [4]
Photo isomer DM019471 N. A. Unclear - Unclear 1 [4]
FG-4592 Metabolites M10 DM019468 N. A. Conjugation - Glucuronidation 2 [4]
FG-4592 Metabolites M10 DM019468 N. A. Hydrolysis - Hydrolysis 2 [4]
FG-4592 Metabolites M11 DM019462 N. A. Oxidation - Sulfonation 2 [4]
FG-4592 Metabolites M6 DM019470 N. A. Unclear - Unclear 2 [4]
FG-4592 Metabolites M7 DM019465 N. A. Hydrolysis - Hydrolysis 2 [4]
FG-4592 Metabolites M9 DM019466 N. A. Conjugation - Glucuronidation 2 [4]
FG-4592 Metabolites M12 DM019463 N. A. Oxidation - Sulfonation 3 [4]
FG-4592 Metabolites M12 DM019463 N. A. Hydrolysis - Hydrolysis 3 [4]
FG-4592 Metabolites M13 DM019464 N. A. Oxidation - Dealkylation 3 [4]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012054 FG-4592 FG-4592 Metabolites M1-M3 Oxidation - Hydroxylation CYP2C8 [4]
MR012061 FG-4592 FG-4592 Metabolites M8 Conjugation - Glucuronidation UGT1A9 [4]
MR012063 FG-4592 FG-4592 Metabolites M4 Unclear - Unclear Unclear [4]
MR012066 FG-4592 FG-4592 Metabolites M5 Oxidation - Dealkylation Unclear [4]
MR012067 FG-4592 Photo isomer Unclear - Unclear Unclear [4]
MR012055 FG-4592 Metabolites M1-M3 FG-4592 Metabolites M11 Oxidation - Sulfonation Unclear [4]
MR012058 FG-4592 Metabolites M1-M3 FG-4592 Metabolites M7 Hydrolysis - Hydrolysis Unclear [4]
MR012060 FG-4592 Metabolites M1-M3 FG-4592 Metabolites M9 Conjugation - Glucuronidation Unclear [4]
MR012064 FG-4592 Metabolites M4 FG-4592 Metabolites M10 Conjugation - Glucuronidation UGT1A9 [4]
MR012065 FG-4592 Metabolites M4 FG-4592 Metabolites M6 Unclear - Unclear Unclear [4]
MR012062 FG-4592 Metabolites M8 FG-4592 Metabolites M10 Hydrolysis - Hydrolysis Unclear [4]
MR012056 FG-4592 Metabolites M11 FG-4592 Metabolites M12 Hydrolysis - Hydrolysis Unclear [4]
MR012057 FG-4592 Metabolites M11 FG-4592 Metabolites M13 Oxidation - Dealkylation Unclear [4]
MR012059 FG-4592 Metabolites M7 FG-4592 Metabolites M12 Oxidation - Sulfonation Unclear [4]
⏷ Show the Full List of 14 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
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
References
1 ClinicalTrials.gov (NCT01750190) A Study of FG-4592 for the Treatment of Anemia in Chronic Kidney Disease Patients Not Receiving Dialysis. U.S. National Institutes of Health.
2 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: 8454).
3 Effect of Kidney Function and Dialysis on the Pharmacokinetics and Pharmacodynamics of Roxadustat, an Oral Hypoxia-Inducible Factor Prolyl Hydroxylase Inhibitor
4 Identification of Hypoxia-inducible factor (HIF) stabilizer roxadustat and its possible metabolites in thoroughbred horses for doping control

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