Atorvastatin

Atorvastatin
Clinical data
Pronunciation/əˌtɔːrvəˈstætən/
Trade namesLipitor, others
AHFS/Drugs.comMonograph
MedlinePlusa600045
License data
Pregnancy
category
Routes of
administration
By mouth
Drug classHypolipidemic agent
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability12%
MetabolismLiver (CYP3A4)
Elimination half-life14 hours
ExcretionBile duct
Identifiers
IUPAC name
  • (3R,5R)-7-[2-(4-Fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.125.464
Chemical and physical data
FormulaC33H35FN2O5
Molar mass558.650 g·mol−1
3D model (JSmol)
SMILES
  • O=C(O)C[C@H](O)C[C@H](O)CCn2c(c(c(c2c1ccc(F)cc1)c3ccccc3)C(=O)Nc4ccccc4)C(C)C
InChI
  • InChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1 Y
  • Key:XUKUURHRXDUEBC-KAYWLYCHSA-N Y
  (verify)

Atorvastatin, sold under the brand name Lipitor among others, is a statin medication used to prevent cardiovascular disease in those at high risk and to treat abnormal lipid levels.[6] For the prevention of cardiovascular disease, statins are a first-line treatment in reducing cholesterol.[6] It is taken by mouth.[6]

Common side effects may include diarrhea, heartburn, nausea, muscle pain (typically mild and dose-dependent) and, less frequently, joint pain. Muscle symptoms often occur during the first year and are commonly influenced by pre-existing health issues and the nocebo effect.[7][8] Most patients can continue therapy with dose adjustment or statin switching. Rare (<0.1%) but serious side effects may include rhabdomyolysis (severe muscle disorder), liver problems and diabetes.[9] Use during pregnancy may harm the fetus.[6] Like all statins, atorvastatin works by inhibiting HMG-CoA reductase, an enzyme found in the liver that plays a role in producing cholesterol.[6]

Atorvastatin was patented in 1986, and approved for medical use in the United States in 1996.[6][10] It is on the World Health Organization's List of Essential Medicines.[11] It is available as a generic medication.[6][12] In 2022, it was the most commonly prescribed medication in the United States, with more than 109 million prescriptions filled for over 27 million people.[13][14] In Australia, it was one of the top ten most prescribed medications between 2017 and 2023.[15]

  1. ^ a b "Atorvastatin (Lipitor) Use During Pregnancy". Drugs.com. 3 February 2020. Archived from the original on 4 December 2019. Retrieved 26 February 2020.
  2. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ^ "Lipitor Product information". Health Canada. 10 March 2017. Retrieved 7 February 2025.
  4. ^ Cite error: The named reference Lipitor FDA label was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Lipitor referral was invoked but never defined (see the help page).
  6. ^ a b c d e f g "Atorvastatin Calcium Monograph for Professionals". Drugs.com. AHFS. Archived from the original on 25 October 2010. Retrieved 23 December 2018.
  7. ^ Cite error: The named reference Reith_2022 was invoked but never defined (see the help page).
  8. ^ Gupta A, Thompson D, Whitehouse A, Collier T, Dahlof B, Poulter N, et al. (ASCOT Investigators) (June 2017). "Adverse events associated with unblinded, but not with blinded, statin therapy in the Anglo-Scandinavian Cardiac Outcomes Trial-Lipid-Lowering Arm (ASCOT-LLA): a randomised double-blind placebo-controlled trial and its non-randomised non-blind extension phase". Lancet. 389 (10088): 2473–2481. doi:10.1016/S0140-6736(17)31075-9. hdl:10044/1/50011. PMID 28476288.
  9. ^ "Australian Medicines Handbook". amhonline.amh.net.au. Retrieved 11 May 2025.
  10. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 473. ISBN 9783527607495. Archived from the original on 12 January 2023. Retrieved 10 May 2020.
  11. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  12. ^ Cite error: The named reference Hit2014 was invoked but never defined (see the help page).
  13. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  14. ^ "Atorvastatin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  15. ^ "Medicines in the health system". Australian Institute of Health and Welfare. 2 July 2024. Retrieved 30 September 2024.