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Desfluoro-ezetimibe

Names

[ CAS No. ]:
302781-98-2

[ Name ]:
Desfluoro-ezetimibe

[Synonym ]:
2-Azetidinone, 3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-1-phenyl-, (3R,4S)-
Desfluoro Ezetimibe
(3R,4S)-3-[(3S)-3-(4-Fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-1-phenyl-2-azetidinone
Ezetimibe Impurity 8

Biological Activity

[Description]:

Desfluoro-ezetimibe is a desfluoro impurity of Ezetimibe. Ezetimibe is a potent, metabolically stable cholesterol absorption inhibitor. Ezetimibe is a Niemann-Pick C1-like1 (NPC1L1) inhibitor, and is a potent Nrf2 activator[1][2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> NF-κB >> Keap1-Nrf2
Research Areas >> Cardiovascular Disease
Signaling Pathways >> Autophagy >> Autophagy

[In Vitro]

During the synthetic process development studies of Ezetimibe, an impurity was detected in the final product at levels ranging from 0.05% to 0.15% in reverse phase gradient high performance liquid chromatography (HPLC) method and its molecular weight is determined by LC–MS analysis. The impurity is Desfluoro-ezetimibe[1].

[References]

[1]. Bellur Atici E, et al. Identification, synthesis and characterization of process related desfluoro impurity of ezetimibe and HPLC method validations. J Pharm Anal. 2015 Dec;5(6):356-370.

[2]. Lee DH, et al. Ezetimibe, an NPC1L1 inhibitor, is a potent Nrf2 activator that protects mice from diet-induced nonalcoholic steatohepatitis. Free Radic Biol Med. 2016 Sep 12;99:520-532.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
642.8±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C24H22FNO3

[ Molecular Weight ]:
391.435

[ Flash Point ]:
342.6±31.5 °C

[ Exact Mass ]:
391.158386

[ PSA ]:
60.77000

[ LogP ]:
3.20

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.635

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds