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14-September-2008 10:43:22 - Atorvastatin Atorvastatin Systematic IUPAC name R-R, R-2-4-fluorophenyl-beta, delta-dihydroxy-5- 1-methylethyl-3-phenyl-4- phenylaminocarbonyl-1H- pyrrole-1-heptanoic acid Identifiers CAS number 134523-00-5 ATC code C10AA05 PubChem 60823 DrugBank APRD00055 Chemical data Formula C33H35FN2O5 Mol. mass 558.64 SMILES eMolecules PubChem Pharmacokinetic data Bioavailability 12% Metabolism Liver Half life 14 hours Excretion Bile Therapeutic considerations Pregnancy cat. DAU XUS Legal status Prescription Only S4AU POMUK ℞-onlyUS Routes oral Atorvastatin INN pronounced /əˌtɔrvəˈstætən/, marketed under the name Lipitor, Lipidra, Aztor, Torvatin, Sortis, Torvast, Torvacard, Totalip, Tulip, Xarator, Atorpic, Liprimar, Atorlip and other names, is a member of the drug class known as statins, used for lowering cholesterol. Atorvastatin inhibits the rate-determining enzyme located in hepatic tissue that produces mevalonate, a small molecule used in the synthesis of cholesterol and other mevalonate derivatives. This lowers the amount of cholesterol produced which in turn lowers the total amount of LDL cholesterol. With 2006 sales of US$12.9 billion under the brand name Lipitor, it is the largest selling drug in the world.1 Lipitor is not the only statin; there are several other statins on the market.23 Contents 1 Pharmacology 2 Clinical use 2.1 Indications 2.2 Available forms 2.3 Adverse effects 3 Patent challenge 4 Pfizer fight against simvastatin alternative 5 Withdrawal of advertisements featuring Dr. Robert Jarvik 6 References 7 External links 8 Further reading 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 LDL uptake by the hepatocytes, decreasing the amount of LDL-cholesterol in the blood. Like other statins, atorvastatin also reduces blood levels of triglycerides and slightly increases levels of HDL-cholesterol. In clinical trials, adding ezetimibe Zetia to Lipitor lowered cholesterol more effectively than Vytorin ezetimibe + simvastatin.citation needed. Clinical use Indications Atorvastatin is indicated as an adjunct to diet for the treatment of dyslipidemia, specifically hypercholesterolaemia. It has also been used in the treatment of combined hyperlipidemia.4 In 2005, the PROVE IT-TIMI 22 trial compared 40mg/day pravastatin with 80mg/day atorvastatin.5 Taken directly from the results of the trial: Standard treatment statin with a 3-hydroxy-3-methylglutaryl coenzyme A HMG-CoA reductase inhibitor pravastatin 40 mg/day resulted in a 22% reduction in LDL cholesterol levels at 30 days compared with a 51% reduction with intensive therapy atorvastatin 80 mg/day. At 2 years, a relative risk reduction of 16% 95% confidence interval, 5%-26%; P = 0.005 in the primary end point rate death, myocardial infarction, documented unstable angina requiring hospitalization, coronary revascularization, or stroke was seen in patients receiving intensive statin treatment compared with standard statin therapy. The benefit of intensive treatment was apparent as early as 30 days and was consistent over time. The PROVE IT-TIMI 22 data indicate that patients recently hospitalized for an ACS benefit from early and continued lowering of LDL cholesterol to levels substantially below current guideline recommendations. Available forms Pack and tablet of Atorvastatin Lipitor® 40mg Pack and tablet of Atorvastatin Lipitor® 40mg 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. Pfizer also packages the drug in combination with other drugs, such as is the case with its Caduet. Adverse effects For additional information see: Statins Common adverse drug reactions ≥1% of patients associated with atorvastatin therapy include: myalgia, mild transient gastrointestinal symptoms diarrhea, constipation, passing gas, elevated hepatic transaminase concentrations, headache, insomnia, joint pain, and/or dizziness.4 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 CYP3A4.4 Patent challenge The size of the market for atorvastatin has prompted the generic drug manufacturing company Ranbaxy to challenge the validity of some of Pfizer's patents in patent courts across the world. As of March 2007, courts had mostly upheld the validity of Pfizer's original patent for atorvastatin, which is due to expire in European territories in 2011 but 2007 in Canada. However a later patent for the specific enantiomer of the atorvastatin formula that is medically useful, which would have given Pfizer longer protection, has fared less well. Although upheld in the United States6, Spain, and Ecuador, the enantiomer patent has been declared invalid by courts in Austria, Australia, Canada, the Netherlands and the United Kingdom7. Pfizer fight against simvastatin alternative After doctors and patients began switching by the millions to a cheaper alternative within the same class of drugs called simvastatin, Pfizer launched a campaign including advertisements, lobbying efforts, and a paid speaking tour by Dr. Louis W. Sullivan, a former secretary of the federal Department of Health and Human Services, to discourage the trend.2 The main clinical advantage of Lipitor over Simvastatin is that it is not metabolised by certain liver enzymes, and thus its blood concentration is not increased when combined with grapefruit juice which inhibits these enzymes. Simvastatin patients should avoid drinking large amounts of grapefruit juice for this reason. An independent analysis showed that, at commonly prescribed doses, atorvastatin and simvastatin have no statistically significant differences in reducing cardiovascular morbidity and mortality.8 Withdrawal of advertisements featuring Dr. Robert Jarvik On February 25, 2008, Pfizer announced that it will voluntarily withdraw all advertisements for Lipitor featuring Dr. Robert Jarvik, and committing to ensuring greater clarity in the roles and responsibilities of its spokespeople in its consumer advertising and promotion. 9 References ^ Loftus, Peter 2007-08-16. Pfizer's Lipitor Patent Reissue Rejected, The Wall Street Journal Online. Retrieved on 2007-08-27. ^ a b Saul, Stephanie; Alex Berenson 2007-11-03. Maker of Lipitor Digs In to Fight Generic Rival. The New York Times. ^ Hawkes, Nigel 2007-10-11. Statins are the right prescription. The Times UK. Retrieved on 2007-11-03. ^ a b c Rossi S, or. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3 ^ Rouleau J 2005. Improved outcome after acute coronary syndromes with an intensive versus standard lipid-lowering regimen: results from the Pravastatin or Atorvastatin Evaluation and Infection Therapy-Thrombolysis in Myocardial Infarction 22 PROVE IT-TIMI 22 trial. Am. J. Med. 118 Suppl 12A: 28-35. doi:10.1016/j.amjmed.2005.09.014. PMID 16356805. ^ BBC News, Patent ruling hits Ranbaxy shares, 19 December 2005 ^ Duncan Bucknell, The global Lipitor patent scorecard, retrieved 2007-03-03 ^ Zhou Z, Rahme E, Pilote L 2006. Are statins created equal? Evidence from randomized trials of pravastatin, simvastatin, and atorvastatin for cardiovascular disease prevention. Am. Heart J. 151 2: 273-81. doi:10.1016/j.ahj.2005.04.003. PMID 16442888. ^ Drugs.com, Pfizer Voluntarily Withdraws Lipitor Advertising Featuring Dr. Robert Jarvik. Retrieved on 2008-03-08. External links Lipitor.com - manufacturer's site MedlinePlus Drug information: Atorvastatin Systemic - information from USP DI Advice for the Patient Further reading Maggon K 2005. Best-selling human medicines 2002-2004. Drug Discov. Today 10 11: 739-42. doi:10.1016/S1359-64460503468-9. PMID 15922927. Lipitor: Prescribing Information. 2004 Pfizer Ireland Pharmaceuticals. v d e Lipid modifying agents C10 Statins HMG-CoA reductase Atorvastatin Cerivastatin‡ Fluvastatin Lovastatin Mevastatin Pitavastatin Pravastatin Rosuvastatin Simvastatin Fibrates PPAR Clofibrate‡ Bezafibrate Aluminium clofibrate Gemfibrozil Fenofibrate Simfibrate Ronifibrate Ciprofibrate Etofibrate Clofibride Clinofibrate Bile acid sequestrants Colestyramine Colestipol Colestilan Colextran Colesevelam Niacin and derivatives Niceritrol Niacin Nicofuranose Aluminium nicotinate Nicotinyl alcohol Acipimox CETP inhibitors Anacetrapib† Torcetrapib§ Combinations Niacin/lovastatin Niacin/simvastatin Ezetimibe/simvastatin Other Dextrothyroxine Probucol Tiadenol Benfluorex Meglutol Omega-3-triglycerides Magnesium pyridoxal 5-phosphate glutamate Policosanol Ezetimibe Lapaquistat§ †Undergoing clinical trials. ‡Withdrawn from market. §Development terminated. Retrieved from http://en..org/wiki/Atorvastatin Categories: Statins | Pyrroles | PfizerHidden categories: All articles with statements | Articles with statements since August 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Bahasa Indonesia Italiano Magyar Nederlands Norsk bokmål Polski Suomi ไทย 中文 This page was last modified on 11 September 2008, at 11:50
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