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

General Information of Drug (ID: DR1487)
Drug Name
Siponimod
Synonyms
Siponimod; Siponimod [INN]; Siponimod [WHO-DD]; BAF-312; BAF312; BAF312 (Siponimod); RR6P8L282I; 1-[[4-[(E)-N-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-C-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid; 1230487-00-9; 3-Azetidinecarboxylic acid, 1-((4-((1E)-1-(((4-cyclohexyl-3-(trifluoromethyl)phenyl)methoxy)imino)ethyl)-2-ethylphenyl)methyl)-; CHEMBL2336071; UNII-RR6P8L282I
Indication Multiple sclerosis [ICD11: 8A40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 516.6 Topological Polar Surface Area 62.1
Heavy Atom Count 37 Rotatable Bond Count 9
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
44599207
CAS Number
1230487-00-9
Formula
C29H35F3N2O3
Canonical SMILES
CCC1=C(C=CC(=C1)C(=NOCC2=CC(=C(C=C2)C3CCCCC3)C(F)(F)F)C)CN4CC(C4)C(=O)O
InChI
1S/C29H35F3N2O3/c1-3-21-14-23(10-11-24(21)15-34-16-25(17-34)28(35)36)19(2)33-37-18-20-9-12-26(22-7-5-4-6-8-22)27(13-20)29(30,31)32/h9-14,22,25H,3-8,15-18H2,1-2H3,(H,35,36)/b33-19+
InChIKey
KIHYPELVXPAIDH-HNSNBQBZSA-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
Siponimod M1 DM002478
154689102
Oxidation - Hydroxylation 1 [2]
Siponimod M17 DM002479
155491262
Unclear 1 [2]
Siponimod M2 DM002480
145349420
Unclear 1 [2]
Siponimod M5 DM002471
146048038
Unclear 1 [2]
Siponimod M6 DM002476
155928780
Unclear 1 [2]
Siponimod M8 DM002481
165412045
Unclear 1 [2]
Siponimod metabolite M7 DM002474 N. A. Unclear 1 [2]
Siponimod M3 DM002473
146048030
Unclear 2 [2]
Siponimod metabolite M4a DM002472 N. A. Unclear 2 [2]
Siponimod metabolite M4B DM002475 N. A. Unclear 2 [2]
Siponimod metabolite M4C DM002477 N. A. Unclear 2 [2]
Siponimod metabolite M7 DM002474 N. A. Unclear 2 [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
MR002269 Siponimod Siponimod metabolite M5 Unclear Unclear [2]
MR002270 Siponimod Siponimod metabolite M7 Unclear Unclear [2]
MR002271 Siponimod Siponimod metabolite M6 Unclear Unclear [2]
MR002272 Siponimod Siponimod metabolite M1 Oxidation - Hydroxylation CYP2C9 ... [2]
MR002273 Siponimod Siponimod metabolite M17 Unclear Unclear [2]
MR002274 Siponimod Siponimod metabolite M2 Unclear Unclear [2]
MR002275 Siponimod Siponimod metabolite M8 Unclear Unclear [2]
MR002264 Siponimod metabolite M5 Siponimod metabolite M4a Unclear Unclear [2]
MR002265 Siponimod metabolite M5 Siponimod metabolite M3 Unclear Unclear [2]
MR002268 Siponimod metabolite M6 Siponimod metabolite M4C Unclear Unclear [2]
MR002266 Siponimod metabolite M7 Siponimod metabolite M7 Unclear Unclear [2]
MR002267 Siponimod metabolite M7 Siponimod metabolite M4B Unclear Unclear [2]
⏷ Show the Full List of 12 MR(s)
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]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Siponimod was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism and disposition of siponimod, a novel selective S1P1/S1P5 agonist, in healthy volunteers and in vitro identification of human cytochrome P450 enzymes involved in its oxidative metabolism. Drug Metab Dispos. 2018 Jul;46(7):1001-1013.

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