General Information of Drug (ID: DMZL1I8)

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
Disease Entry ICD 11 Status REF
Diabetic complication 5A2Y Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 279.22
Logarithm of the Partition Coefficient (xlogp) -0.3
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C12H10FN3O4
IUPAC Name
(2S,4S)-6-fluoro-2',5'-dioxospiro[2,3-dihydrochromene-4,4'-imidazolidine]-2-carboxamide
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
Cross-matching ID
PubChem CID
160024
CAS Number
136087-85-9
DrugBank ID
DB02021
TTD ID
D00EWR

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aldose reductase (AKR1B1) TTFBNVI ALDR_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Interleukin-13 (IL13) OTI4YS3Y IL13_HUMAN Protein Interaction/Cellular Processes [3]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [3]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [3]
Signal transducer and activator of transcription 6 (STAT6) OTCKMP49 STAT6_HUMAN Post-Translational Modifications [3]
Tyrosine-protein kinase JAK1 (JAK1) OT0X3D17 JAK1_HUMAN Post-Translational Modifications [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Diabetic complication
ICD Disease Classification 5A2Y
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Aldose reductase (AKR1B1) DTT AKR1B1 1.08E-20 0.94 1.58
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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 Clinical efficacy of fidarestat, a novel aldose reductase inhibitor, for diabetic peripheral neuropathy: a 52-week multicenter placebo-controlled double-blind parallel group study. Diabetes Care. 2001 Oct;24(10):1776-82.
3 Aldose reductase inhibition prevents metaplasia of airway epithelial cells. PLoS One. 2010 Dec 28;5(12):e14440. doi: 10.1371/journal.pone.0014440.