124782-63-4

Basic information

• Product Name: (Z,Z)-5-(2-Methyl-3-phenyl-propenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic Acid
• Synonyms: (Z,Z)-5-(2-Methyl-3-phenyl-propenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic Acid;Epalrestat isomer;CHNUOJQWGUIOLD-NQXFEYKRSA-N
• CAS NO: 124782-63-4
• Molecular Formula: C₁₅H₁₃NO₃S₂
• Molecular Weight: 333.4252
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 124782-63-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 516.8±60.0 °C(Predicted)
• Appearance: /
• Density: 1.43±0.1 g/cm3(Predicted)
• PKA: 3.62±0.10(Predicted)
• CAS DataBase Reference: (Z,Z)-5-(2-Methyl-3-phenyl-propenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (Z,Z)-5-(2-Methyl-3-phenyl-propenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic Acid(124782-63-4)
• EPA Substance Registry System: (Z,Z)-5-(2-Methyl-3-phenyl-propenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic Acid(124782-63-4)

Safety Data

• Hazardous Substances Data: 124782-63-4(Hazardous Substances Data)

Usage

Description

(Z,Z)-5-(2-Methyl-3-phenyl-propenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic Acid is a complex organic compound characterized by its unique molecular structure, featuring a thiazolidine ring and a phenyl group. It is a stereoisomer of Epalrestat (E565300), an aldose reductase inhibitor, and possesses potential therapeutic properties.

Uses

Used in Pharmaceutical Industry:
(Z,Z)-5-(2-Methyl-3-phenyl-propenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic Acid is used as a therapeutic agent for the treatment of diabetic neuropathy. Its mechanism of action involves inhibiting aldose reductase, an enzyme implicated in the development of diabetic complications, thereby potentially alleviating symptoms and slowing the progression of neuropathy in diabetic patients.

Upstream product

• 124782-64-5 {5-[(Z)-2-Methyl-3-phenyl-prop-2-en-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid 
• 863988-85-6 epalrestate 
• 5718-83-2 rhodanine 3-acetic acid 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 
• 82158-86-9 Epalrestat 

Downstream Products

• 124782-64-5 {5-[(Z)-2-Methyl-3-phenyl-prop-2-en-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid 
• 863988-85-6 epalrestate 
• 1206474-03-4 epalrestat 1-(2-hydroxyethyl)-pyrrolidine salt 
• 1206474-02-3 epalrestat sodium salt 
• 1206474-01-2 epalrestat potassium salt 

Relevant articles and documents

Simultaneous Improvement of Epalrestat Photostability and Solubility via Cocrystallization: A Case Study

In this study, we attempt to simultaneously improve the photostability and solubility of epalrestat (a drug used for neuropathy treatment) by preparing epalrestat-betaine zwitterionic cocrystals and characterize the physicochemical property alterations ac

New epalrestat crystal form as well as preparation method and application thereof

The invention belongs to the technical field of medicines, and provides a novel epalrestat crystal form as well as a preparation method and application thereof. The X-ray powder diffraction pattern of the epalrestat new crystal form has characteristic diffraction peaks when the diffraction angles 2 theta are 6.39 +/-0.2 degrees, 7.57 +/-0.2 degrees, 12.69 +/-0.2 degrees, 14.67 +/-0.2 degrees, 15.04 +/-0.2 degrees, 21.79 +/-0.2 degrees, 24.36 +/-0.2 degrees, 25.59 +/-0.2 degrees, 27.30 +/-0.2 degrees and 31.48 +/-0.2 degrees. The epalrestat novel crystal form has excellent dissolution performance and water solubility, and the bioavailability of the epalrestat novel crystal form is improved; moreover, the epalrestat new crystal form has excellent flowability, the angle of repose can reach 26 degrees or below, the compression coefficient is smaller than 10%, the Hausner ratio is 1.00-1.11, and the epalrestat new crystal form is suitable for being used as a raw material medicine for production of prodrugs or pharmaceutical preparations of the epalrestat new crystal form.

STRUCTURAL ELUCIDATION OF EPALRESTAT(ONO-2235), A POTENT ALDOSE REDUCTASE INHIBITOR, AND ISOMERIZATION OF ITS DOUBLE BONDS

The structure of epalrestat (ONO-2235) is revised by X-ray single crystal analysis.The structures of the photoisomers are proposed on the basis of NMR and UV spectroscopic evidences.