3918. Ezetimibe

Nomenclature

CAS number: 163222-33-1
(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone; Sch-58235; Ezetrol (Merck/Schering-Plough); Zetia (Merck/Schering-Plough).
C24H21F2NO3; mol wt 409.43.
C 70.40%, H 5.17%, F 9.28%, N 3.42%, O 11.72%.

Description and references

Cholesterol absorption inhibitor. Prepn: S. B. Rosenblum et al., WO 9508532; eidem, US 5767115 (1995, 1998 both to Schering); idem et al., J. Med. Chem. 41, 973 (1998). Enantioselective synthesis: G. Wu et al., J. Org. Chem. 64, 3714 (1999). Activity in animals: M. van Heek et al., J. Pharmacol. Exp. Ther. 283, 157 (1997). Metabolism and distribution: eidem, Br. J. Pharmacol. 129, 1748 (2000). Review of pharmacology and clinical studies: H. Bays, Expert Opin. Invest. Drugs 11, 1587-1604 (2002).

Chemical structure

Properties

White solid, mp 164-166°. [α]D22 -33.9° (c = 3 in methanol).

Therapeutic Category

Antilipemic.

Keywords

Antilipemic