190448-57-8

Basic information

• Product Name: EZETIMIBE PHENOXY GLUCURONIDE
• Synonyms: EZETIMIBE PHENOXY GLUCURONIDE;EZETIMIBE B-D-GLUCURONIDE;4-[(2S,3R)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-2-azetidinyl]phenyl-D-Glucopyranosiduronic Acid;Ezetimibe -D-Glucuronide, >85%;EZM-G;Sch 58235 Glucuronide;Sch 60663;Ezetimibe β-D-Glucuronide, >90%
• CAS NO: 190448-57-8
• Molecular Formula: C30H29F2NO9
• Molecular Weight: 585.55
• Product Categories: Glucuronides;Inhibitors;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 190448-57-8.mol

Chemical Properties

• Melting Point: 140-150°C
• Appearance: /
• Refractive Index: 1.65
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: EZETIMIBE PHENOXY GLUCURONIDE(CAS DataBase Reference)
• NIST Chemistry Reference: EZETIMIBE PHENOXY GLUCURONIDE(190448-57-8)
• EPA Substance Registry System: EZETIMIBE PHENOXY GLUCURONIDE(190448-57-8)

Safety Data

• Hazardous Substances Data: 190448-57-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
EZETIMIBE PHENOXY GLUCURURONIDE is used as a Phase-II metabolite for its role in cholesterol absorption inhibition. As a metabolite of Ezetimibe, it contributes to the overall efficacy of the drug in managing hyperlipoproteinemia, which is a condition characterized by elevated levels of lipoproteins in the blood. This application aids in the treatment and prevention of cardiovascular diseases by reducing the absorption of cholesterol and promoting overall cardiovascular health.
Used in Research and Development:
In the field of research and development, EZETIMIBE PHENOXY GLUCURURONIDE serves as a valuable compound for studying the metabolic pathways and pharmacokinetics of Ezetimibe. Understanding the behavior and effects of this metabolite can lead to the development of more effective drugs and therapies for managing cholesterol levels and related health conditions.
Used in Quality Control and Standardization:
EZETIMIBE PHENOXY GLUCURURONIDE is utilized in the quality control and standardization of pharmaceutical products containing Ezetimibe. As a specific metabolite, it can be used to ensure the purity, potency, and consistency of these products, thereby maintaining the safety and efficacy of the medications for patients.

InChI:InChI=1/C30H29F2NO9/c31-17-5-1-15(2-6-17)22(34)14-13-21-23(33(28(21)38)19-9-7-18(32)8-10-19)16-3-11-20(12-4-16)41-30-26(37)24(35)25(36)27(42-30)29(39)40/h1-12,21-27,30,34-37H,13-14H2,(H,39,40)/t21-,22+,23-,24?,25-,26?,27?,30+/m1/s1

Upstream product

• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 72692-06-9 methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 
• 190448-46-5 (1S)-1-(4-fluorophenyl)-3-[(2S,3R)-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]propyl acetate 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 190448-56-7 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[(2S,3R)-3-[(S)-3-acetoxy-3-(4-fluoro-phenyl)-propyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 

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).

Sugar-Substituted 2-Azetidinone Cholesterol Absorption Inhibitors: Enhanced Potency by Modification of the Sugar

A glucuronide conjugate of the potent 2-azetidinone cholesterol absorbtion inhibitor Sch 58235 was synthesized to confirm the structure of a metabolite isolated from in vivo sources.A series of 2-azetidinone glycosides was prepared via Schmidt trichloroim