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

General Information of Drug (ID: DR0697)
Drug Name
Fingolimod hydrochloride
Synonyms
Fingolimod (FTY720) HCl; Fingolimod (hydrochloride); Fingolimod HCl; Fingolimod hydrochloride; Fingolimod hydrochloride [USAN]; Fty 720; FTY-720; Fty-720; FTY720; Gilenia; Gilenya; Q-101363; 162359-56-0; 2-AMINO-2-[2-(4-OCTYL-PHENYL)-ETHYL]-PROPANE-1,3-DIOL HCL; 2-Amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol hydrochloride; 2-Amino-2-(4-octylphenethyl)propane-1,3-diol hydrochloride; 2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride; AK-33554; CHEBI:63112; G926EC510T; UNII-G926EC510T
Indication Multiple sclerosis [ICD11: 8A40] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 343.9 Topological Polar Surface Area 66.5
Heavy Atom Count 23 Rotatable Bond Count 12
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
107969
PubChem SID
10234529 ; 12014880 ; 14900483 ; 26758737 ; 44436887 ; 47206133 ; 50021117 ; 53600034 ; 53800768 ; 57338355 ; 85171085 ; 92719820 ; 98528441 ; 99300584 ; 99436939 ; 103669455 ; 104380162 ; 109692984 ; 117672600 ; 118842531 ; 124757869 ; 124772071 ; 125164672 ; 125342329 ; 126522748 ; 126628080 ; 126648547 ; 126666984 ; 126731322 ; 134339028 ; 134339285 ; 134964386 ; 135066165 ; 135727426 ; 136345852 ; 136367507 ; 136367937 ; 136920394 ; 136964585 ; 137065890 ; 143493393 ; 144115996 ; 152233650 ; 152258330 ; 160647169 ; 162011674 ; 162037993 ; 162185346 ; 163378868 ; 163688106
ChEBI ID
CHEBI:63112
CAS Number
162359-56-0
TTD Drug ID
D0HI1K
Formula
C19H34ClNO2
Canonical SMILES
CCCCCCCCC1=CC=C(C=C1)CCC(CO)(CO)N.Cl
InChI
1S/C19H33NO2.ClH/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;1H
InChIKey
SWZTYAVBMYWFGS-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 [5] , [6]
Fingolimod carboxylic acid metabolite DM000183 N. A. Oxidation - Hydroxylation 1 [5]
Non-polar ceramides analogs of fingolimod DM000185 N. A. Unclear 1 [5]
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
MR001045 Fingolimod hydrochloride Fingolimod carboxylic acid metabolite Oxidation - Hydroxylation CYP4F2 [5]
MR001046 Fingolimod hydrochloride (S)-enantiomer of fingolimod-phosphate Other reaction - Phosphorylation SPHK1 [5], [6]
MR001047 Fingolimod hydrochloride Non-polar ceramides analogs of fingolimod Unclear Unclear [5]
MR001048 Fingolimod hydrochloride . Unclear CYP3A4 [3]
MR001044 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
[4]
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
[5]
⏷ Show the Full List of 8  DME(s)
References
1 ClinicalTrials.gov (NCT00513279) To Investigate If Single Doses Of GSK618334 Are Safe And To Investigate Blood Levels Of GSK618334.
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 Product information - Gilenya.
5 Clinical pharmacokinetics of fingolimod Clin Pharmacokinet. 2012 Jan 1;51(1):15-28. doi: 10.2165/11596550-000000000-00000.
6 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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