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

General Information of Drug (ID: DR0696)
Drug Name
Fingolimod
Prodrug Info Fingolimod is the prodrug of (S)-enantiomer of fingolimod-phosphate
Synonyms
Fingolimod; Fingolimod (INN); Fingolimod [INN]; fingolimodum; 1,3-Propanediol, 2-amino-2-[2-(4-octylphenyl)ethyl]-; 162359-55-9; 2-Amino-2-(4-octylphenethyl)propane-1,3-diol; 2-Amino-2-[2-(4-octylphenyl)ethyl]-1,3-propandiol; 2-Amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol; 2-Amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol; 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol; 2-amino-2-(2-(4-octylphenyl)ethyl)propane-1,3-diol; 3QN8BYN5QF; C19H33NO2; CHEBI:63115; CHEMBL314854; UNII-3QN8BYN5QF
Indication Multiple sclerosis [ICD11: 8A40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 307.5 Topological Polar Surface Area 66.5
Heavy Atom Count 22 Rotatable Bond Count 12
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
107970
PubChem SID
7980354 ; 10627340 ; 11538030 ; 14800795 ; 44436888 ; 50070757 ; 52231945 ; 91613352 ; 103298437 ; 104045114 ; 104380165 ; 112629137 ; 124899206 ; 125335078 ; 126522750 ; 126659901 ; 126665797 ; 128394615 ; 134339282 ; 135204658 ; 135626722 ; 135650261 ; 137003753 ; 140236536 ; 152344348 ; 160820803 ; 162221744 ; 163091250 ; 163838506 ; 164834614 ; 174006739 ; 175268765 ; 175426965 ; 175427125 ; 184527777 ; 204414213 ; 210274752 ; 210280385 ; 223660888 ; 223770775 ; 226398832 ; 242078815 ; 249836440 ; 251873579 ; 251916753 ; 251917992 ; 252214240 ; 252433026 ; 252478872
ChEBI ID
CHEBI:63115
CAS Number
162359-55-9
TTD Drug ID
D07UHS
Formula
C19H33NO2
Canonical SMILES
CCCCCCCCC1=CC=C(C=C1)CCC(CO)(CO)N
InChI
1S/C19H33NO2/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)13-14-19(20,15-21)16-22/h9-12,21-22H,2-8,13-16,20H2,1H3
InChIKey
KKGQTZUTZRNORY-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
(S)-enantiomer of fingolimod-phosphate DM000184 N. A. Other reaction - Phosphorylation 1 [4] , [5]
Fingolimod carboxylic acid metabolite DM000183 N. A. Oxidation - Hydroxylation 1 [4]
Non-polar ceramides analogs of fingolimod DM000185 N. A. Unclear 1 [4]
Unclear DM009999 N. A. Unclear 1 [3]
Unclear DM009999 N. A. Oxidation - Oxidation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001040 Fingolimod Fingolimod carboxylic acid metabolite Oxidation - Hydroxylation CYP4F2 [4]
MR001041 Fingolimod (S)-enantiomer of fingolimod-phosphate Other reaction - Phosphorylation SPHK1 [4], [5]
MR001042 Fingolimod Non-polar ceramides analogs of fingolimod Unclear Unclear [4]
MR001043 Fingolimod . Unclear CYP3A4 [3]
MR001039 Fingolimod carboxylic acid metabolite . Oxidation - Oxidation Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 4F12 (CYP4F12) DME0135 Homo sapiens
CP4FC_HUMAN
1.14.14.1
[2]
Cytochrome P450 4F2 (CYP4F2) DME0025 Homo sapiens
CP4F2_HUMAN
1.14.13.30
[2]
Flavin-containing monooxygenase (FMO) DMEN075 . Not Available Not Available [2]
Leukotriene B4 omega-hydroxylase (CYP4F3) DME0034 Homo sapiens
CP4F3_HUMAN
1.14.14.1
[2]
Sphingosine kinase 1 (SPHK1) DME0484 Homo sapiens
SPHK1_HUMAN
2.7.1.91
[4]
⏷ Show the Full List of 8  DME(s)
References
1 Fingolimod was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 CYP4F enzymes are responsible for the elimination of fingolimod (FTY720), a novel treatment of relapsing multiple sclerosis. Drug Metab Dispos. 2011 Feb;39(2):191-8.
3 LABEL:INGOLIMOD capsule
4 Clinical pharmacokinetics of fingolimod Clin Pharmacokinet. 2012 Jan 1;51(1):15-28. doi: 10.2165/11596550-000000000-00000.
5 Ketoconazole increases fingolimod blood levels in a drug interaction via CYP4F2 inhibition J Clin Pharmacol. 2009 Feb;49(2):212-8. doi: 10.1177/0091270008329553.

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