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

General Information of Drug (ID: DR3480)
Drug Name
Esonarimod
Synonyms Sonatimod; KE-298; KE-749; KE-758; NE-298; (R)-KE-298; (S)-KE-298
Indication Rheumatoid arthritis [ICD11: FA20] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 280.34 Topological Polar Surface Area 96.7
Heavy Atom Count 19 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
127998
ChEBI ID
CHEBI:31559
CAS Number
101973-77-7
TTD Drug ID
D0MY7X
Formula
C14H16O4S
Canonical SMILES
CC1=CC=C(C=C1)C(=O)CC(CSC(=O)C)C(=O)O
InChI
InChI=1S/C14H16O4S/c1-9-3-5-11(6-4-9)13(16)7-12(14(17)18)8-19-10(2)15/h3-6,12H,7-8H2,1-2H3,(H,17,18)
InChIKey
YRSSFEUQNAXQMX-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
Deacetyl-esonarimod(M1) DM015235
177955
Unclear - Unclear 1 [2]
S-methyl-esonarimod(M2) DM015693
10468245
Unclear - Unclear 2 [2]
4-hydroxy-S-methyl-esonarimod DM019472 N. A. Unclear - Unclear 3 [3]
Sulfoxide-S-methyl-esonarimod DM019473 N. A. Unclear - Unclear 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012069 Esonarimod Deacetyl-esonarimod(M1) Unclear - Unclear Unclear [2]
MR012070 Deacetyl-esonarimod(M1) S-methyl-esonarimod(M2) Unclear - Unclear FMO5 ... [2]
MR012071 S-methyl-esonarimod(M2) 4-hydroxy-S-methyl-esonarimod Unclear - Unclear Unclear [3]
MR012072 S-methyl-esonarimod(M2) Sulfoxide-S-methyl-esonarimod Unclear - Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Dimethylaniline oxidase 5 (FMO5) DME0634 Homo sapiens
FMO5_HUMAN
1.14.13.8
[2]
References
1 KE-758, an active metabolite of the new anti-rheumatic drug KE-298, suppresses production of tumor necrosis factor-alpha and interleukin-1 beta in THP-1, a human monocyte cell line. Drugs Exp Clin Res. 2002;28(5):197-205.
2 S-oxidation of S-methyl-esonarimod by flavin-containing monooxygenases in human liver microsomes
3 Identification of Hypoxia-inducible factor (HIF) stabilizer roxadustat and its possible metabolites in thoroughbred horses for doping control

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