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Details

Stereochemistry ACHIRAL
Molecular Formula C15H13NO3S2.C15H12NO3S2.C5H14NO
Molecular Weight 741.96
Optical Activity NONE
Defined Stereocenters 0 / 1
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of DIEPALRESTAT CHOLINE

SMILES

C[N+](C)(C)CCO.CC(=C/C1=CC=CC=C1)\C=C2/SC(=S)N(CC(O)=O)C2=O.CC(=C/C3=CC=CC=C3)\C=C4/SC(=S)N(CC([O-])=O)C4=O

InChI

InChIKey=WKSNHZZSMLFYFI-UROVXFGGSA-M
InChI=1S/2C15H13NO3S2.C5H14NO/c2*1-10(7-11-5-3-2-4-6-11)8-12-14(19)16(9-13(17)18)15(20)21-12;1-6(2,3)4-5-7/h2*2-8H,9H2,1H3,(H,17,18);7H,4-5H2,1-3H3/q;;+1/p-1/b2*10-7+,12-8-;

HIDE SMILES / InChI
Molecular Formula C15H13NO3S2
Molecular Weight 319.399
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE
Molecular Formula C5H13NO
Molecular Weight 103.1628
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity NONE

Description

Epalrestat is an aldose reductase inhibitor that is approved in Japan for the improvement of subjective neuropathy symptoms, abnormality of vibration sense, and abnormal changes in heart beat associated with diabetic peripheral neuropathy.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Aldose reductase
45
Target ID: P15121
Gene ID: 231.0
Gene Symbol: AKR1B1
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 0.28 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
KINEDAK

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.9 μg/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/18447661/
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPALRESTAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
6.4 μg × h/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/18447661/
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPALRESTAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
9.9%
REVIEW
https://pubmed.ncbi.nlm.nih.gov/18447661/
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPALRESTAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
50 mg 3 times / day multiple, oral
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
unhealthy
Health Status: unhealthy
Sex: unknown
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
Disc. AE: Thrombocytopenia, unspecified, Jaundice, unspecified, not of newborn...
AEs leading to
discontinuation/dose reduction:
Thrombocytopenia, unspecified (serious)
Jaundice, unspecified, not of newborn (serious)
Hepatic failure (serious)
Acute fulminant hepatitis (serious)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
AEs

AEs

AESignificanceDosePopulation
Acute fulminant hepatitis serious
Disc. AE
50 mg 3 times / day multiple, oral
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
unhealthy
Health Status: unhealthy
Sex: unknown
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
Hepatic failure serious
Disc. AE
50 mg 3 times / day multiple, oral
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
unhealthy
Health Status: unhealthy
Sex: unknown
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
Jaundice, unspecified, not of newborn serious
Disc. AE
50 mg 3 times / day multiple, oral
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
unhealthy
Health Status: unhealthy
Sex: unknown
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
Thrombocytopenia, unspecified serious
Disc. AE
50 mg 3 times / day multiple, oral
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
unhealthy
Health Status: unhealthy
Sex: unknown
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/18447661/
PubMed

PubMed

TitleDatePubMed
AKR1B10 induces cell resistance to daunorubicin and idarubicin by reducing C13 ketonic group.
2011-08-15
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011-07-14
Abnormal axonal inward rectifier in streptozocin-induced experimental diabetic neuropathy.
2001-06
Therapeutic effects of aldose reductase inhibitor on experimental diabetic neuropathy through synthesis/secretion of nerve growth factor.
1998-06
Patents

Patents

JP2001163805A
2
JP2002536332A
39
JP2004051520A
2
JP2004210702A
2
JP2004210703A
2
JP2004210766A
2
JP2004210775A
2
JP2005139085A
3
JP2005139086A
3
JP2005298424A
2
JP2006104064A
2
JP2006111601A
2
JP2006282526A
2
JP2006528156A
10
JP2007099680A
2
JP2007505083A
6
JP2007505085A
6
JP2009029717A
2
JP2011507800A
49
JP5294046B2
2

Sample Use Guides

In Vivo Use Guide
50 mg, 3 times/day
Route of Administration: Oral
In Vitro Use Guide
Human umbilical vein endothelial cells were cultured for 48 h in glucose-rich (27.8 mM) medium. The increased neutrophil-endothelial cell adhesion and surface expression of intercellular adhesion molecule-1 (ICAM-1), P-selectin, and E-selectin on endothelial cells was inhibited by 10 microM of epalrestat.
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:21:10 GMT 2025
Edited
by admin
on Mon Mar 31 23:21:10 GMT 2025
Record UNII
16AHE7410O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHANAMINIUM, 2-HYDROXY-N,N,N-TRIMETHYL-, (5Z)-5-((2E)-2-METHYL-3-PHENYL-2-PROPEN-1-YLIDENE)-4-OXO-2-THIOXO-3-THIAZOLIDINEACETATE, (5Z)-5-((2E)-2-METHYL-3-PHENYL-2-PROPEN-1-YLIDENE)-4-OXO-2-THIOXO-3-THIAZOLIDINEACETATE (1:1:1)
Preferred Name English
DIEPALRESTAT CHOLINE
Common Name English
Code System Code Type Description
PUBCHEM
117587644
Created by admin on Mon Mar 31 23:21:10 GMT 2025 , Edited by admin on Mon Mar 31 23:21:10 GMT 2025
PRIMARY
CAS
1665300-21-9
Created by admin on Mon Mar 31 23:21:10 GMT 2025 , Edited by admin on Mon Mar 31 23:21:10 GMT 2025
PRIMARY
FDA UNII
16AHE7410O
Created by admin on Mon Mar 31 23:21:10 GMT 2025 , Edited by admin on Mon Mar 31 23:21:10 GMT 2025
PRIMARY
Related Record Type Details
Structure of EPALRESTAT
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of EPALRESTAT
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