Atorvastatin
Systematic (IUPAC) name
[R-(R*, R*)]-2-(4-fluorophenyl)-beta, delta-dihydroxy-5- (1-methylethyl)-3-phenyl-4- [(phenylamino)carbonyl]-1H- pyrrole-1-heptanoic acid
Identifiers
CAS number	134523-00-5
ATC code	C10AA05
PubChem	60823
DrugBank	APRD00055
Chemical data
Formula	C33H34FN2O5
Mol. weight	558.64
Pharmacokinetic data
Bioavailability	12%
Metabolism	Liver
Half life	14 hours
Excretion	Bile
Therapeutic considerations
Pregnancy cat.	D(AU) X(US) Atorvastatin, prominent statin drug, drawn in bkchem and GIMP by Mykhal. ... Image File history File links Download high-resolution version (1100x1035, 252 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Atorvastatin ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Metabolism (from Greek μεταβολισμός metabolismos) is the biochemical modification of chemical compounds in living organisms and cells. ... The liver is the largest internal organ of the human body. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... Bile (or gall) is a bitter, greenish-yellow alkaline fluid secreted by hepatocytes from the liver of most vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... Motto: None Anthem: Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney English (de facto 1) Government Constitutional monarchy (federal)  - Queen Elizabeth II  - Governor-General Michael Jeffery  - Prime Minister John Howard Independence from the UK   - Constitution 1 January 1901   - Statute of Westminster 11 December 1931... United States is the current Good Article Collaboration of the week! Please help to improve this article to the highest of standards. ...
Legal status	S4(AU) POM(UK) ℞-only(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... Motto: None Anthem: Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney English (de facto 1) Government Constitutional monarchy (federal)  - Queen Elizabeth II  - Governor-General Michael Jeffery  - Prime Minister John Howard Independence from the UK   - Constitution 1 January 1901   - Statute of Westminster 11 December 1931... United States is the current Good Article Collaboration of the week! Please help to improve this article to the highest of standards. ...
Routes	oral

Atorvastatin (INN) (IPA: [əˈtɔvəˌstætn]) is a member of the drug class known as statins, used for lowering cholesterol and thereby reducing cardiovascular disease. Atorvastatin inhibits a rate-determining enzyme located in hepatic tissue used in cholesterol synthesis, which lowers the amount of cholesterol produced. This also has the effect of lowering the total amount of LDL cholesterol. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... For information on how to read IPA transcriptions of English words see here. ... Lovastatin, the first statin to be marketed The statins (or HMG-CoA reductase inhibitors) form a class of hypolipidemic agents, used as pharmaceuticals to lower cholesterol levels in people at risk for cardiovascular disease because of hypercholesterolemia. ... Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. ... It has been suggested that this article or section be merged with Coronary heart disease. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... The liver is the largest internal organ of the human body. ... Low-density lipoprotein (LDL) refers to a class and range of lipoprotein particles, varying somewhat in their size and contents, which carry cholesterol in the blood and around the body, for use by various cells. ...

With 2005 sales of US$12.2 billion under the brand name Lipitor, it is the largest selling drug in the world.

Pharmacology

Main article: Statin

As with other statins, atorvastatin is a competitive inhibitor of HMG-CoA reductase. Unlike most others, however, it is a completely synthetic compound. HMG-CoA reductase catalyzes the reduction of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) to mevalonate, which is the rate-limiting step in hepatic cholesterol biosynthesis. Inhibition of the enzyme decreases de novo cholesterol synthesis, increasing expression of low-density lipoprotein receptors (LDL receptors) on hepatocytes. This increases the LDL uptake by the hepatocytes, decreasing the amount of LDL in the blood. Lovastatin, the first statin to be marketed The statins (or HMG-CoA reductase inhibitors) form a class of hypolipidemic agents, used as pharmaceuticals to lower cholesterol levels in people at risk for cardiovascular disease because of hypercholesterolemia. ... An enzyme inhibitor is a molecule that binds to an enzyme and decreases its rate of reaction. ... HMG-CoA reductase (or 3-hydroxy-3-methyl-glutaryl-CoA reductase or HMGR) is the first enzyme (EC 1. ... Generally, synthetic means pertaining to synthesis, i. ... The HMG-CoA reductase pathway, also known as MVA pathway or mevalonate-dependent (MAD) route, is an important cellular metabolic pathway present in virtually all organisms. ... Mevalonic acid is a key organic compound in biochemistry. ... The rate-determining step is a chemistry term for the slowest step in a chemical reaction. ... Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. ... In law, the expression trial de novo literally means new trial. It is most often used in certain legal systems that provide for one form of trial, then another if a party remains unsatisfied with the decision. ... Brown and Goldstein won a Nobel Prize for their identification of the Low Density Lipoprotein (LDL) receptor 30 years ago whilst they were studying the disease familiar hypercholesterolaemia. ... Hepatocytes make up 60-80% of the cytoplasmic mass of the liver. ...

Clinical use

Indications

Atorvastatin is indicated as an adjunct to diet for the treatment of dyslipidaemia, specifically hypercholesterolaemia. It has also been used in the treatment of combined hyperlipidemia.^[1] Hypercholesterolemia (literally: high blood cholesterol) is the presence of high levels of cholesterol in the blood. ... Hypercholesterolemia (literally: high blood cholesterol) is the presence of high levels of cholesterol in the blood. ... In medicine, combined hyperlipidemia (or -aemia) is a commonly occurring form of hypercholesterolemia (elevated cholesterol levels) characterised by increased LDL and triglyceride concentrations, often accompanied by decreased HDL. On lipoprotein electrophoresis (a test now rarely performed) is shows as a hyperlipoproteinemia type IIB. The elevated triglyceride levels (>5 mmol/l...

Available forms

Atorvastatin calcium tablets are currently marketed by Pfizer under the trade name Lipitor, in tablets (10, 20, 40 or 80 mg) for oral administration. Tablets are white, elliptical, and film coated. In some countries it may also be known as: Sortis, Torvast, Totalip, Tulip, Xarator or Liprimar. Pfizer, Incorporated (NYSE: PFE), is the worlds largest pharmaceutical company based in New York City. ...

Adverse effects

For additional information see: Statin#Safety

Common adverse drug reactions (≥1% of patients) associated with atorvastatin therapy include: myalgia, mild transient gastrointestinal symptoms, elevated hepatic transaminase concentrations, headache, insomnia, and/or dizziness.^[1] Lovastatin, the first statin to be marketed The statins (or HMG-CoA reductase inhibitors) form a class of hypolipidemic agents, used as pharmaceuticals to lower cholesterol levels in people at risk for cardiovascular disease because of hypercholesterolemia. ... An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... Myalgia means muscle pain and is a symptom of many diseases and disorders. ... In biochemistry, a transaminase or an aminotransferase is an enzyme that catalyzes a type of reaction between an amino acid and an α-keto acid. ...

Myopathy and rhabdomyolysis occur in <0.1% of patients. Risk is increased in patients with renal impairment, serious concurrent illness; and/or concomitant use of drugs which inhibit CYP3A4.^[1] In medicine, a myopathy is a neuromuscular disease in which the muscle fibers dysfunction for any one of many reasons, resulting in muscular weakness. ... Rhabdomyolysis is the breakdown of skeletal muscle due to injury, either mechanical, physical or chemical. ... Renal failure is the condition in which the kidneys fail to function properly. ... Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ...

References

The Australian Medicines Handbook or AMH is a medical reference text commonly used in practice by health professionals (particularly general practitioners and pharmacists) in Australia. ...

External links

• Lipitor.com – manufacturer's site
• MedlinePlus Drug information: Atorvastatin (Systemic) – information from USP DI Advice for the Patient

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Further reading

• Maggon, Krishan. "Best-selling human medicines 2002-2004 (editorial)". 2005. Drug Discovery Today, 10(11):739-742. DOI:10.1016/S1359-6446(05)03468-9
• Lipitor: Prescribing Information. (2004) Pfizer Ireland Pharmaceuticals.

A digital object identifier (or DOI) is a permanent identifier (permalink) given to a World Wide Web file or other Internet document so that if its Internet address changes, users will be redirected to its new address. ...