Details of the Drug

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]
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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
UNII: 8SH8T1164U
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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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)

MEA Detail

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.