204589-58-2

Basic information

• Product Name: EzetiMibe Dehydoxy IMpurity
• Synonyms: EzetiMibe Dehydoxy IMpurity;(3R,4S)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)propyl)-4-(4-hydroxyphenyl)azetidin-2-one
• CAS NO: 204589-58-2
• Molecular Formula: C24H21F2NO2
• Molecular Weight: 393.43
• Mol File: 204589-58-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 614.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.275±0.06 g/cm3(Predicted)
• PKA: 9.72±0.30(Predicted)
• CAS DataBase Reference: EzetiMibe Dehydoxy IMpurity(CAS DataBase Reference)
• NIST Chemistry Reference: EzetiMibe Dehydoxy IMpurity(204589-58-2)
• EPA Substance Registry System: EzetiMibe Dehydoxy IMpurity(204589-58-2)

Safety Data

• Hazardous Substances Data: 204589-58-2(Hazardous Substances Data)

Usage

Description

EzetiMibe Dehydoxy IMpurity, also known as 3-Dehydroxy Ezetimibe, is a derivative of Ezetimibe (E975000), which is an antihyperlipoproteinemic agent. It functions as a cholesterol absorption inhibitor, playing a significant role in the management of hyperlipidemia and related cardiovascular conditions.

Uses

Used in Pharmaceutical Industry:
EzetiMibe Dehydoxy IMpurity is used as an active pharmaceutical ingredient (API) for the development of medications aimed at reducing cholesterol levels in patients with hyperlipidemia. Its application is crucial in the treatment of conditions associated with high cholesterol, such as atherosclerosis, coronary artery disease, and other cardiovascular diseases.
Used in Research and Development:
EzetiMibe Dehydoxy IMpurity serves as a valuable compound in the field of research and development, particularly in the study of cholesterol metabolism and the development of novel therapeutic strategies for managing hyperlipidemia and related health issues. Its use in research contributes to the advancement of medical knowledge and the discovery of new treatment options for patients.
Used in Quality Control and Regulatory Compliance:
EzetiMibe Dehydoxy IMpurity is utilized in the quality control processes of pharmaceutical manufacturing, ensuring the safety, efficacy, and purity of Ezetimibe-based medications. It is also essential in meeting regulatory requirements and guidelines for the approval and marketing of cholesterol-lowering drugs.

Upstream product

• 204589-96-8 (3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-propyl]-azetidin-2-one 
• 352-34-1 4-fluoro-1-iodobenzene 
• 591-80-0 pent-4-enoic acid 
• 24484-54-6 2-[3-(4-fluorophenyl)propyl]malonic acid 
• 70627-52-0 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine 
• 204589-92-4 5-(4-fluorophenyl)pentanoyl chloride 
• 24484-22-8 5-(4-fluorophenyl)-pentanoic acid 
• 371-40-4 4-fluoroaniline 
• 459-57-4 4-fluorobenzaldehyde 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 204589-68-4 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-2-E-propenyl]-4-(4-hydroxyphenyl)-2-azetidinone 
• 204589-94-6 5-(4-fluorophenyl)-3-pentenoic acid 

Relevant articles and documents

First synthesis of N-(4-fluorophenyl)-5-(4-fluorophenyl)-2(4- hydroxybenzyl)pentanamide, a new potential cholesterol absorption inhibitor

The first synthesis of N-(4-fluorophenyl)-5-(4-fluorophenyl)-2-(4- hydroxybenzyl)pentanamide and a new synthesis of 1-(4-fluorophenyl)-3-[(4- fluorophenyl)propyl]-4-(4-hydroxyphenyl)-2-azetidinone starting from 4- fluorobenzaldehyde are described. This new amide could represent a potential new cholesterol absorption inhibitor.

Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)- hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): A designed, potent, orally active inhibitor of cholesterol absorption

(3R)-(3-Phenylpropyl)-1,(4S)-bis(4-methoxyphenyl)-2-azetidinone (2, SCH 48461), a novel inhibitor of intestinal cholesterol absorption, has recently been described by Burnett et al. and has been demonstrated to lower total plasma cholesterol in man. The potential sites of metabolism of 2 were considered, and the most probable metabolites were prepared. The oral cholesterol-lowering efficacy of the putative metabolites was evaluated in a 7-day cholesterol-fed hamster model for the reduction of serum total cholesterol and liver cholesteryl esters versus control. On the basis of our analysis of the putative metabolite structure-activity relationship (SAR), SCH 58235 (1, 1-4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]- (4S)-(4-hydroxyphenyl)-2-azetidinone) was designed to exploit activity enhancing oxidation and to block sites of potential detrimental metabolic oxidation. Additionally, a series of congeners of 2 were prepared incorporating strategically placed hydroxyl groups and fluorine atoms to further probe the SAR of 2-azetidinone cholesterol absorption inhibitors. Through the SAR analysis of a series of putative metabolites of 2, compound 1 was targeted and found to exhibit remarkable efficacy with an ED50 of 0.04 mg/kg/day for the reduction of liver cholesteryl esters in a 7-day cholesterol-fed hamster model.