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Atorvastatin information


Atorvastatin
Clinical data
Pronunciation/əˌtɔːrvəˈstætən/
Trade namesLipitor, others
AHFS/Drugs.comMonograph
MedlinePlusa600045
License data
  • US DailyMed: Atorvastatin
Pregnancy
category
  • AU: D[1]
  • Contraindicated[1]
Routes of
administration
By mouth
ATC code
  • C10AA05 (WHO) C10BX08 (WHO) C10BX03 (WHO) C10BA05 (WHO) C10BA08 (WHO) C10BX15 (WHO) C10BX12 (WHO) C10BX06 (WHO) C10BX11 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[2]
  • UK: POM (Prescription only)
  • US: ℞-only[3]
  • EU: Rx-only"Lipitor". European Medicines Agency. 17 September 2018. Retrieved 26 February 2023.</ref>
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
  • 134523-00-5 checkY
PubChem CID
  • 60823
IUPHAR/BPS
  • 2949
DrugBank
  • APRD00055 ☒N
ChemSpider
  • 54810 checkY
UNII
  • A0JWA85V8F
KEGG
  • D07474 checkY
ChEBI
  • CHEBI:39548 checkY
ChEMBL
  • ChEMBL1487 checkY
PDB ligand
  • 117 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID8029868 Edit this at Wikidata
ECHA InfoCard100.125.464 Edit this at Wikidata
Chemical and physical data
FormulaC33H35FN2O5
Molar mass558.650 g·mol−1
3D model (JSmol)
  • Interactive image
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 checkY
  • Key:XUKUURHRXDUEBC-KAYWLYCHSA-N checkY
  (verify)

Atorvastatin is a statin medication used to prevent cardiovascular disease in those at high risk and to treat abnormal lipid levels.[4] For the prevention of cardiovascular disease, statins are a first-line treatment.[4] It is taken by mouth.[4]

Common side effects include joint pain, diarrhea, heartburn, nausea, and muscle pains.[4] Serious side effects may include rhabdomyolysis, liver problems, and diabetes.[4] Use during pregnancy may harm the fetus.[4] Like all statins, atorvastatin works by inhibiting HMG-CoA reductase, an enzyme found in the liver that plays a role in producing cholesterol.[4]

Atorvastatin was patented in 1986, and approved for medical use in the United States in 1996.[4][5] It is on the World Health Organization's List of Essential Medicines.[6] It is available as a generic medication.[4][7] In 2021, it was the most commonly prescribed medication in the United States, with more than 116 million prescriptions filled for over 28 million patients.[8][9]

  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. ^ Cite error: The named reference Lipitor label was invoked but never defined (see the help page).
  4. ^ a b c d e f g h i "Atorvastatin Calcium Monograph for Professionals". Drugs.com. AHFS. Archived from the original on 25 October 2010. Retrieved 23 December 2018.
  5. ^ 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.
  6. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  7. ^ Cite error: The named reference Hit2014 was invoked but never defined (see the help page).
  8. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  9. ^ "Atorvastatin - Drug Usage Statistics". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

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Atorvastatin

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Atorvastatin is a statin medication used to prevent cardiovascular disease in those at high risk and to treat abnormal lipid levels. For the prevention...

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Statin

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cardiovascular disease. There are various forms of statins, some of which include atorvastatin, fluvastatin, lovastatin, pitavastatin, pravastatin, rosuvastatin, and...

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Rosuvastatin

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patients with hypercholesterolemia than milligram-equivalent doses of atorvastatin and milligram-equivalent or higher doses of simvastatin and pravastatin...

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WHO Model List of Essential Medicines

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Streptokinaseα Simvastatin Acetylsalicylic acid/atorvastatin/ramipril (acetylsalicylic acid + atorvastatin + ramipril) Acetylsalicylic...

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Ranbaxy Laboratories

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dispute with Pfizer, allowing them to sell atorvastatin calcium, the generic version of Lipitor and atorvastatin calcium-amlodipine besylate, the generic...

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Fluvastatin

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for statins, can also occur. Contrary to lovastatin, simvastatin and atorvastatin, fluvastatin has no relevant interactions with drugs that inhibit the...

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Subdural hematoma

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atorvastatin, dexamethasone, and mannitol, although supporting conservative treatment is still weak. HMG-CoA reductase inhibitor such as Atorvastatin...

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Drug nomenclature

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name or trademark name. For example, Lipitor is Pfizer's trade name for atorvastatin, a cholesterol-lowering medication. Many drugs have multiple trade names...

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Chiral auxiliary

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strategies for setting a key stereocenter in Tipranavir The calcium salt of atorvastatin is marketed under the trade name Lipitor for the lowering of blood cholesterol...

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ATC code C10

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Simvastatin C10AA02 Lovastatin C10AA03 Pravastatin C10AA04 Fluvastatin C10AA05 Atorvastatin C10AA06 Cerivastatin C10AA07 Rosuvastatin C10AA08 Pitavastatin C10AB01...

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Amlodipine

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variety of medications: Amlodipine/atorvastatin, where amlodipine is given for hypertension or CAD and atorvastatin prevents cardiovascular events, or...

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Torcetrapib

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all-cause mortality in the treatment group receiving a combination of atorvastatin (Lipitor) and torcetrapib. Torcetrapib has not been found to reduce either...

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Mexazolam

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inhibitors including simvastatin, simvastatin acid, lovastatin, fluvastatin, atorvastatin and cerivastatin inhibit the metabolism of mexazolam, but not the HMG-CoA...

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Fluorine

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insulation and cookware, and PTFE (Teflon). Pharmaceuticals such as atorvastatin and fluoxetine contain C−F bonds. The fluoride ion from dissolved fluoride...

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Bruce Roth

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University and the University of Rochester, and, at the age of 32, discovered atorvastatin, the statin-class drug sold as Lipitor that would become the largest-selling...

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with Warner–Lambert for Lipitor (atorvastatin), a statin for the treatment of hypercholesterolemia. Although atorvastatin was the fifth statin to be developed...

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Medicinal chemistry

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often divided into the broad classes of small organic molecules (e.g., atorvastatin, fluticasone, clopidogrel) and "biologics" (infliximab, erythropoietin...

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Phenyl group

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aromatic substitutions. Representative compounds containing phenyl groups Atorvastatin (Lipitor), a blockbuster drug featuring two phenyl and one p-fluorophenyl...

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Aortic aneurysm

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non-HDL-cholesterol, improves lesion stability and adds to the beneficial effects of atorvastatin Elevating the amount of HDL cholesterol in the abdominal area of the...

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CADASIL

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pressure is particularly important in CADASIL patients. Short-term use of atorvastatin, a statin-type cholesterol-lowering medication, has not been shown to...

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Ezetimibe

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available in the fixed combinations ezetimibe/simvastatin, ezetimibe/atorvastatin, ezetimibe/rosuvastatin, and ezetimibe/bempedoic acid. The most commonly...

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Pitavastatin

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70-month CIRCLE observational study, pitavastatin increased HDL more than atorvastatin. It has neutral or possibly beneficial effects on glucose control. As...

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Influenza A virus

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on influenza virus replication show that pre-treatment of cells with atorvastatin suppresses virus growth in culture. Highly pathogenic H5N1 avian influenza...

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Hyperlipidemia

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fatty acid production. Statin drugs, especially the synthetic statins (atorvastatin and rosuvastatin) can decrease LDL levels by increasing hepatic reuptake...

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