Ezetimibe

Ezetimibe
Clinical data
Pronunciation	/ɛˈzɛtɪmɪb, -maɪb/
Trade names	Zetia, Ezetrol, others
AHFS/Drugs.com	Monograph
MedlinePlus	a603015
License data	US DailyMed: Ezetimibe;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
Drug class	Cholesterol absorption inhibitor
ATC code	C10AX09 (WHO) C10BA05 (WHO) C10BA06 (WHO) C10BA02 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	35% to 65%
Protein binding	>90%
Metabolism	Intestinal wall, liver
Elimination half-life	19 h to 30 h
Excretion	Kidney 11%, fecal 78%
Identifiers
	IUPAC name (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one;
CAS Number	163222-33-1 ;
PubChem CID	150311;
IUPHAR/BPS	6816;
DrugBank	DB00973 ;
ChemSpider	132493 ;
UNII	EOR26LQQ24;
KEGG	D01966 ;
ChEBI	CHEBI:49040 ;
ChEMBL	ChEMBL1138 ;
CompTox Dashboard (EPA)	DTXSID1044223 ;
ECHA InfoCard	100.207.996
Chemical and physical data
Formula	C24H21F2NO3
Molar mass	409.433 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	164 to 166 °C (327 to 331 °F)
	SMILES Fc1ccc(cc1)[C@@H](O)CC[C@H]4C(=O)N(c2ccc(F)cc2)[C@@H]4c3ccc(O)cc3;
	InChI InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1 ; Key:OLNTVTPDXPETLC-XPWALMASSA-N ;
	(verify)

Ezetimibe is a medication used to treat high blood cholesterol and certain other lipid abnormalities. Generally it is used together with dietary changes and a statin. Alone, it is less preferred than a statin. It is taken by mouth. It is also available in the fixed combinations ezetimibe/simvastatin, ezetimibe/atorvastatin, ezetimibe/rosuvastatin, and ezetimibe/bempedoic acid.

The most commonly reported adverse events include upper respiratory tract infections, joint pain, diarrhea, and tiredness. Serious side effects may include anaphylaxis, liver problems, depression, and muscle breakdown. Use in pregnancy and breastfeeding is of unclear safety. Ezetimibe works by decreasing cholesterol absorption in the intestines.

Ezetimibe was approved for medical use in the United States in 2002. It is available as a generic medication. In 2021, it was the 92nd most commonly prescribed medication in the United States, with more than 7 million prescriptions.

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