Epalrestat

Base Information

• Chemical Name: Epalrestat
• CAS No.: 82159-09-9
• Molecular Formula: C₁₅H₁₃NO₃S₂
• Molecular Weight: 319.405
• European Community (EC) Number: 675-018-0
• UNII: 424DV0807X
• DSSTox Substance ID: DTXSID1046479
• Nikkaji Number: J211.576J,J823.055B
• Wikipedia: Epalrestat
• Wikidata: Q5382029
• NCI Thesaurus Code: C72762
• Pharos Ligand ID: TW9BA8K15VZA
• Metabolomics Workbench ID: 155400
• ChEMBL ID: CHEMBL56337
• Mol file: 82159-09-9.mol

Synonyms:3-carboxymethyl-5-(methyl-3-phenylpropenylidene)rhodanine;epalrestat;ONO 2;ONO 2235;ONO-2;ONO-2235

Chemical Property of Epalrestat

Chemical Property:

• Appearance/Colour: Deep red acicular crystal
• Vapor Pressure: 1.66E-11mmHg at 25°C
• Melting Point: 210-217 °C
• Refractive Index: 1.705
• Boiling Point: 516.8 °C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 266.4 °C
• PSA: 115.00000
• Density: 1.43 g/cm³
• LogP: 2.85660
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble5mg/mL, clear (warmed)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 319.03368562
• Heavy Atom Count: 21
• Complexity: 519

Purity/Quality:

99.2% ^*data from raw suppliers

Epalrestat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1=CC=CC=C1)C=C2C(=O)N(C(=S)S2)CC(=O)O
• Isomeric SMILES: C/C(=C\C1=CC=CC=C1)/C=C\2/C(=O)N(C(=S)S2)CC(=O)O
• Recent ClinicalTrials: Research of SORD-CMT Natural History and Epalrestat Treatment
• Recent NIPH Clinical Trials: Epalrestat effect on diabetic neuropathy in primary care setting
• Description: Epalrestat is the second aldose reductase inhibitor to be introduced worldwide and the first to be launched in Japan. The compound is indicated for the treatment of diabetic neuropathy. It is also being investigated for diabetic retinopathy and nephropathy.
• Uses: Epalrestat has been used as an aldose reductase inhibitor: in the dahomey larvae diet fed forDrosophilafor non-irradiated and X-ray irradiated human aldose reductaseto test its protective effect in mice with bleomycin-induced pulmonary fibrosis Epalrestat is an aldose reductase inhibitor with IC50 of 72 nM An aldose reductase inhibitor. It is used in treatment of diabetic neuropathy.

Technology Process of Epalrestat

There total 3 articles about Epalrestat which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

rhodanine 3-acetic acid (5718-83-2) + α-methyl-trans-cinnamaldehyde (15174-47-7) → Epalrestat (82158-86-9,82159-09-9,124782-63-4,124782-64-5)

Guidance literature:

With 1-amino-3-(dimethylamino)propane; In water; at 60 ℃; for 2h;

Reference yield:

{5-[(Z)-2-Methyl-3-phenyl-prop-2-en-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid (124782-64-5) → Epalrestat (82158-86-9,82159-09-9,124782-63-4,124782-64-5) + 5-[(1Z,2Z)-2-methyl-3-phenylpropenylidene]-4-oxo-2-thioxo-3-thiazolidineacetic acid (124782-63-4)

Guidance literature:

Product distribution; even in dark;

DOI:10.1016/S0040-4039(00)95290-0

Reference yield:

epalrestate (863988-85-6) → Epalrestat (82158-86-9,82159-09-9,124782-63-4,124782-64-5) + 5-[(1Z,2Z)-2-methyl-3-phenylpropenylidene]-4-oxo-2-thioxo-3-thiazolidineacetic acid (124782-63-4)

Guidance literature:

Product distribution; even in dark;

DOI:10.1016/S0040-4039(00)95290-0

upstream raw materials:

{5-[(Z)-2-Methyl-3-phenyl-prop-2-en-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid

epalrestate

rhodanine 3-acetic acid

α-methyl-trans-cinnamaldehyde

Refernces

• 1、 -. "New epalrestat crystal form as well as preparation method and application thereof". Paragraph 0079-0081; 0103-0114. . Retrieved 2021/11/19.
• 2、 Ishida, Toshimasa,In, Yasuko,Inoue, Masatoshi,Ueno, Yoko,Tanaka, Chiaki,Hamanaka, Nobuyuki. "STRUCTURAL ELUCIDATION OF EPALRESTAT(ONO-2235), A POTENT ALDOSE REDUCTASE INHIBITOR, AND ISOMERIZATION OF ITS DOUBLE BONDS". . p. 959 - 962. Retrieved 2007/10/02.