190448-56-7

Basic information

• Product Name: 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester
• Synonyms: 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester;4-[(2S,3R)-3-[(3S)-3-(Acetyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxo-2-azetidinyl]phenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate;3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl-2-D-glucuronide Methyl Ester
• CAS NO: 190448-56-7
• Molecular Formula: C₃₉H₃₉F₂NO₁₃
• Molecular Weight: 767.7226664
• Product Categories: Aromatics;Glucuronides;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 190448-56-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 808.9±65.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: -0.43±0.60(Predicted)
• CAS DataBase Reference: 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester(190448-56-7)
• EPA Substance Registry System: 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester(190448-56-7)

Safety Data

• Hazardous Substances Data: 190448-56-7(Hazardous Substances Data)

Usage

Description

3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester is a chemical compound that serves as an intermediate in the preparation of Phase-II metabolites of Ezetimibe. It is a glucuronide azetidinone cholesterol absorption inhibitor, which plays a crucial role in the development of pharmaceuticals targeting cholesterol regulation. This white solid is a significant component in the synthesis of drugs that help manage cholesterol levels in the body.

Uses

Used in Pharmaceutical Industry:
3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester is used as an intermediate for the synthesis of Phase-II metabolites of Ezetimibe. It plays a vital role in the development of cholesterol absorption inhibitors, which are essential for managing cholesterol levels in the body.
Used in Drug Development:
As a glucuronide azetidinone cholesterol absorption inhibitor, 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester is used in the development of drugs that target the regulation of cholesterol. Its chemical properties make it a valuable component in creating effective pharmaceuticals for treating conditions related to high cholesterol.
Used in Research and Development:
3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester is also utilized in research and development for the study of cholesterol metabolism and the development of novel therapeutic strategies for managing cholesterol-related health issues. Its unique properties allow scientists to explore new avenues in the treatment and prevention of cardiovascular diseases.

Upstream product

• 72692-06-9 methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 
• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 190448-46-5 (1S)-1-(4-fluorophenyl)-3-[(2S,3R)-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]propyl acetate 

Downstream Products

• 190448-57-8 [14C]-Ezetimibe glucuronide 

Relevant articles and documents

An in vitro assay for evaluation of small-molecule inhibitors of cholesterol absorption

Giving cholesterol the brush off: An intestinal brush border membrane vesicle assay has been devised for the convenient in vitro testing of small molecules for inhibition of cholesterol absorption. The assay was used to identify new nonhydrolyzable glycosides as potent cholesterol-absorption inhibitors and an oxazolidinone as an effective replacement of the β-lactam scaffold of ezetimibe (1).