Ezetimibe

Ezetimibe
Above: molecular structure of ezetimibe Below: 3D representation of an ezetimibe molecule
Clinical data
Pronunciation/ɛˈzɛtɪmɪb, -maɪb/
Trade namesZetia, others
AHFS/Drugs.comMonograph
MedlinePlusa603015
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classCholesterol absorption inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability35% to 65%
Protein binding>90%
MetabolismIntestinal wall, liver
Elimination half-life19 h to 30 h
ExcretionKidney 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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.207.996
Chemical and physical data
FormulaC24H21F2NO3
Molar mass409.433 g·mol−1
3D model (JSmol)
Melting point164 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 Y
  • Key:OLNTVTPDXPETLC-XPWALMASSA-N Y
  (verify)

Ezetimibe, sold under the brand name Zetia among others, is a medication used to treat high blood cholesterol and certain other lipid abnormalities.[2][3] Generally it is used together with dietary changes and a statin.[4] Alone, it is less preferred than a statin.[3] It is taken by mouth.[3] It is also available in the fixed-dose combinations ezetimibe/simvastatin,[5] ezetimibe/atorvastatin,[6] ezetimibe/rosuvastatin,[3][7] and ezetimibe/bempedoic acid.[8]

The most commonly reported adverse events include upper respiratory tract infections, joint pain, diarrhea, and tiredness.[3] Serious side effects may include anaphylaxis, liver problems, depression, and muscle breakdown.[3][4] Use in pregnancy and breastfeeding is of unclear safety.[9] Ezetimibe works by decreasing cholesterol absorption in the intestines.[4]

Ezetimibe was approved for medical use in the United States in 2002.[3] It is available as a generic medication.[4] In 2022, it was the 79th most commonly prescribed medication in the United States, with more than 8 million prescriptions.[10][11]

  1. ^ a b "AusPAR: Ezetimibe". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 20 April 2024.
  2. ^ a b "Zetia- ezetimibe tablet". DailyMed. 26 January 2011. Archived from the original on 10 May 2021. Retrieved 13 August 2022.
  3. ^ a b c d e f g "Ezetimibe Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 17 June 2019. Retrieved 13 April 2019.
  4. ^ a b c d British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 196. ISBN 9780857113382.
  5. ^ "Vytorin- ezetimibe and simvastatin tablet". DailyMed. 1 June 2022. Archived from the original on 14 August 2022. Retrieved 13 August 2022.
  6. ^ "Liptruzet (ezetimibe and atorvastatin) tablets for oral useInitial U.S. Approval: 2013". DailyMed. 30 September 2016. Archived from the original on 14 August 2022. Retrieved 13 August 2022.
  7. ^ "Roszet- rosuvastatin and ezetimibe tablet Roszet (- rosuvastatin and ezetimibe tablet". DailyMed. 15 September 2021. Archived from the original on 14 August 2022. Retrieved 13 August 2022.
  8. ^ "Nexlizet- bempedoic acid and ezetimibe tablet, film coated". DailyMed. 24 September 2021. Retrieved 13 August 2022.
  9. ^ "Ezetimibe (Zetia) Use During Pregnancy". Drugs.com. Archived from the original on 13 April 2019. Retrieved 13 April 2019.
  10. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  11. ^ "Ezetimibe Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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