Details of the Drug

General Information of Drug (ID: DM5OGK0)

Drug Name
Epalrestat
Synonyms
epalrestat; 82159-09-9; Kinedak; Epalrestatum; Ono 2235; Ono-2235; Epalrestat [INN]; Epalrestatum [Latin]; ONO-2; 2-((z)-5-((e)-2-methyl-3-phenylallylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid; ONO 2; UNII-424DV0807X; C15H13NO3S2; CHEMBL56337; 5-((1Z,2E)-2-Methyl-3-phenylpropenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic acid; CHEBI:31539; 5-((Z,E)-beta-Methylcinnamylidene)-4-oxo-2-thioxo-3-thiazolidineacetic acid; 424DV0807X; Epalrestatum; Aldorin (TN); Kinedak (TN); Epalrestat (JAN/INN); {5-[(E)-2-Methyl-3-phenyl-prop-2-en-(Z)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid; {(5Z)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic acid; 2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid; 3-carboxymethyl-5-(methyl-3-phenylpropenylidene)rhodanine; Ono 2
Indication
Disease Entry ICD 11 Status REF
Diabetic neuropathy 8C0Z Approved [1]
Pain MG30-MG3Z Investigative [2]
Therapeutic Class
Hypoglycemic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 319.4
Logarithm of the Partition Coefficient (xlogp) 3.8
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 6.709 micromolar/kg/day [3]
Chemical Identifiers
Formula
C15H13NO3S2
IUPAC Name
2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
Canonical SMILES
C/C(=C\\C1=CC=CC=C1)/C=C\\2/C(=O)N(C(=S)S2)CC(=O)O
InChI
InChI=1S/C15H13NO3S2/c1-10(7-11-5-3-2-4-6-11)8-12-14(19)16(9-13(17)18)15(20)21-12/h2-8H,9H2,1H3,(H,17,18)/b10-7+,12-8-
InChIKey
CHNUOJQWGUIOLD-NFZZJPOKSA-N
Cross-matching ID
PubChem CID
1549120
ChEBI ID
CHEBI:31539
CAS Number
82159-09-9
DrugBank ID
DB15293
TTD ID
D03KOZ
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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 [4]
Voltage-gated L-type calcium channel (L-CaC) TTXHYV6 NOUNIPROTAC Blocker [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Hypoxia-inducible factor 1-alpha (HIF1A) OTADSC03 HIF1A_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Diabetic neuropathy
ICD Disease Classification 8C0Z
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 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 Recent updates of N-type calcium channel blockers with therapeutic potential for neuropathic pain and stroke. Curr Top Med Chem. 2009;9(4):377-95.
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 Long-term effect of epalrestat, an aldose reductase inhibitor, on the development of incipient diabetic nephropathy in Type 2 diabetic patients. J Diabetes Complications. 2001 Sep-Oct;15(5):241-4.
5 Epalrestat Stimulated Oxidative Stress, Inflammation, and Fibrogenesis in Mouse Liver. Toxicol Sci. 2018 Jun 1;163(2):397-408. doi: 10.1093/toxsci/kfx038.