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

General Information of Drug (ID: DR3397)
Drug Name
Fidarestat
Synonyms
Aldos; FID; Fidaresstat; SK 860; Snk 860; Aldos (TN); SNK-860; Fidarestat (JAN/INN); (+)-(2S,4S)-6-Fluoro-2',5'-dioxospiro(chroman-4,4'-imidazolidine)-2-carboxamide; (+)-(2s,4s)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide; (2S,4S)-2-AMINOFORMYL-6-FLUORO-SPIRO[CHROMAN-4,4'-IMIDAZOLIDINE]-2',5'-DIONE; (2S,4S)-6-Fluoro-2',5'-dioxospiro(3,4-dihydro-2H-1-benzopyran-4,4'-imidazolidine)-2-carboxamide; (2S,4S)-6-fluoro-2',5'-dioxospiro(chroman-4,4'-imidazolidine)-2-carboxamide; (2S,4S)-6-fluoro-2',5'-dioxospiro[2,3-dihydrochromene-4,4'-imidazolidine]-2-carboxamide
Indication Diabetic complication [ICD11: 5A2Y] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 279.22 Topological Polar Surface Area 111
Heavy Atom Count 20 Rotatable Bond Count 1
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
160024
CAS Number
136087-85-9
TTD Drug ID
D00EWR
Formula
C12H10FN3O4
Canonical SMILES
C1[C@H](OC2=C([C@]13C(=O)NC(=O)N3)C=C(C=C2)F)C(=O)N
InChI
InChI=1S/C12H10FN3O4/c13-5-1-2-7-6(3-5)12(4-8(20-7)9(14)17)10(18)15-11(19)16-12/h1-3,8H,4H2,(H2,14,17)(H2,15,16,18,19)/t8-,12-/m0/s1
InChIKey
WAAPEIZFCHNLKK-UFBFGSQYSA-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
Fidarestat Metabolite F1 DM015853
13935991
Multi-steps Reaction - Oxidation; deamination 1 [3] , [2]
Fidarestat Metabolite F11 DM017640 N. A. Multi-steps Reaction - Hydroxylation; glycosylation 1 [3]
Fidarestat Metabolite F14 DM017637 N. A. Other reaction - Cysteamination 1 [3]
Fidarestat Metabolite F15 DM017642 N. A. Multi-steps Reaction - Hydroxylation; cysteamination 1 [3]
Fidarestat Metabolite F16 DM017641 N. A. Conjugation - N-acetylation 1 [3]
Fidarestat Metabolite F17 DM017638 N. A. Oxidation - Dihydroxylation 1 [3]
Fidarestat Metabolite F18 DM017639 N. A. Conjugation - Glucuronidation 1 [3]
Fidarestat Metabolite F3 DM016574
129722571
Multi-steps Reaction - Reduction; defluroniation 1 [3]
Fidarestat Metabolite F4 DM017643 N. A. Reduction - Hydrogenation 1 [3]
Fidarestat Metabolite F5 DM017644 N. A. Oxidation - Trihydroxylation 1 [3]
Fidarestat Metabolite F6 DM017636 N. A. Oxidation - Methylation 1 [3]
Fidarestat Metabolite F8 DM017635 N. A. Multi-steps Reaction - Oxidation; acetylation 1 [3]
Fidarestat Metabolite F9 DM017634 N. A. Conjugation - Glycosylation 1 [3]
Fidarestat Metabolite F10 DM017633 N. A. Conjugation - Glycosylation 2 [3]
Fidarestat Metabolite F12 DM017631 N. A. Conjugation - Glucuronidation 2 [3]
Fidarestat Metabolite F2 DM017629 N. A. Oxidation - Hydroxylation 2 [3]
Fidarestat Metabolite F7 DM017632 N. A. Conjugation - Acetylation 2 [3]
Fidarestat Metabolite F13 DM017630 N. A. Conjugation - Glucuronidation 3 [3]
⏷ Show the Full List of 18  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009091 Fidarestat Fidarestat Metabolite F1 Multi-steps Reaction - Oxidation; deamination CYP1A2 ... [3], [2]
MR009097 Fidarestat Fidarestat Metabolite F3 Multi-steps Reaction - Reduction; defluroniation Unclear [3]
MR009098 Fidarestat Fidarestat Metabolite F9 Conjugation - Glycosylation Unclear [3]
MR009099 Fidarestat Fidarestat Metabolite F8 Multi-steps Reaction - Oxidation; acetylation Unclear [3]
MR009100 Fidarestat Fidarestat Metabolite F6 Oxidation - Methylation Unclear [3]
MR009101 Fidarestat Fidarestat Metabolite F14 Other reaction - Cysteamination Unclear [3]
MR009102 Fidarestat Fidarestat Metabolite F17 Oxidation - Dihydroxylation Unclear [3]
MR009103 Fidarestat Fidarestat Metabolite F18 Conjugation - Glucuronidation Unclear [3]
MR009104 Fidarestat Fidarestat Metabolite F11 Multi-steps Reaction - Hydroxylation; glycosylation Unclear [3]
MR009105 Fidarestat Fidarestat Metabolite F16 Conjugation - N-acetylation Unclear [3]
MR009106 Fidarestat Fidarestat Metabolite F15 Multi-steps Reaction - Hydroxylation; cysteamination Unclear [3]
MR009107 Fidarestat Fidarestat Metabolite F4 Reduction - Hydrogenation Unclear [3]
MR009108 Fidarestat Fidarestat Metabolite F5 Oxidation - Trihydroxylation Unclear [3]
MR009092 Fidarestat Metabolite F1 Fidarestat Metabolite F2 Oxidation - Hydroxylation Unclear [3]
MR009094 Fidarestat Metabolite F1 Fidarestat Metabolite F12 Conjugation - Glucuronidation Unclear [3]
MR009095 Fidarestat Metabolite F1 Fidarestat Metabolite F7 Conjugation - Acetylation Unclear [3]
MR009096 Fidarestat Metabolite F1 Fidarestat Metabolite F10 Conjugation - Glycosylation Unclear [3]
MR009093 Fidarestat Metabolite F2 Fidarestat Metabolite F13 Conjugation - Glucuronidation Unclear [3]
⏷ Show the Full List of 18 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
References
1 X-ray structure of the V301L aldo-keto reductase 1B10 complexed with NADP(+) and the potent aldose reductase inhibitor fidarestat: implications for inhibitor binding and selectivity. Chem Biol Interact. 2013 Feb 25;202(1-3):178-85.
2 Plasma protein binding, pharmacokinetics, tissue distribution and CYP450 biotransformation studies of fidarestat by ultra high performance liquid chromatography-high resolution mass spectrometry
3 Identification and characterization of in vitro and in vivo fidarestat metabolites: Toxicity and efficacy evaluation of metabolites

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