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Atorvastatin, marketed under the trade name Lipitor among others, is a member of the medication class known as statins, which are used primarily as a lipid-lowering agent and for prevention of events associated with cardiovascular disease. Like all statins, atorvastatin works by inhibiting HMG-CoA reductase, an enzyme found in liver tissue that plays a key role in production of cholesterol in the body.
Atorvastatin was first made in August 1985 at Warner-Lambert ‘s Parke-Davis research facility in Ann Arbor, Michigan
1 Medical uses
1.2 Cardiovascular disease
1.3 Other uses
2.1 Specific populations
4 Adverse effects
5 Mechanism of action
9 Chemical synthesis
12 Generic availability
13 Medication recalls
15 Further reading
16 External links
The primary uses of atorvastatin is for the treatment of dyslipidemia and the prevention of cardiovascular disease :
Hypercholesterolemia as well as increase HDL levels.
Heterozygous familial hypercholesterolemia in pediatric patients
Homozygous familial hypercholesterolemia
Hypertriglyceridemia ( Fredrickson Type IV )
Primary dysbetalipoproteinemia ( Fredrickson Type III )
Primary prevention of heart attack, stroke, and need for revascularization procedures in patients who have risk factors such as age, smoking, high blood pressure, low HDL-C, and a family history of early heart disease, but have not yet developed clinically evident coronary artery disease.
Secondary prevention of myocardial infarction, stroke, unstable angina,
Myocardial infarction and stroke prophylaxis in patients with type II diabetes
There have been recent studies suggesting that high-dose statin therapy plays a plaque-stabilizing role in people suffering from acute coronary syndrome and thrombotic stroke.
Atorvastatin may be used in combination with bile acid sequestrants and ezetimibe to increase the reduction in cholesterol levels. However, It is not recommended to combine statin medication treatment with certain other cholesterol-lowering medications, particularly fibrates, because this may increase the risk of myopathy-related adverse effects.
While many statin medications should be administered at bedtime for optimal effect, atorvastatin can be dosed at any time of day, as long as it is continually dosed once daily at the same time.
Geriatric : Plasma concentrations of atorvastatin in healthy elderly subjects are higher than those in young adults, and clinical data suggests a greater degree of LDL-lowering at any dose for patients in the population as compared to young adults.
Pediatric : Pharmacokinetic data is not available for this population.
Gender : Plasma concentrations are generally higher in women than in men, but there is no clinically significant difference in the extent of LDL reduction between men and women.
Renal impairment : Renal disease has no influence on plasma concentrations of atorvastatin and dosing need not be adjusted in these patients.
Hemodialysis : Hemodialysis will not significantly alter medication levels or change clinical effect of atorvastatin.
Hepatic impairment : In patients with chronic alcoholic liver disease, levels of atorvastatin may be significantly increased depending upon the extent of liver disease.
Active liver disease: cholestasis, hepatic encephalopathy, hepatitis, and jaundice
Unexplained elevations in AST or ALT levels
Pregnancy : Atorvastatin may cause fetal harm by affecting serum cholesterol and triglyceride levels, which are essential for fetal development.
Breastfeeding : Small amounts of other statin medications have been found to pass into breast milk, although atorvastatin has not been studied, specifically.
Markedly elevated CPK levels or if a myopathy is suspected or diagnosed after dosing of atorvastatin has begun. Very rarely, atorvastatin may cause rhabdomyolysis,
Type 2 diabetes mellitus, an uncommon class effect of all statins.
Myopathy with elevation of creatine kinase (CK, aka CPK) As mentioned previously, atorvastatin should be discontinued immediately if this occurs.
Persistent liver enzyme abnormalities occurred in 0.7% of patients who received atorvastatin in clinical trials. It is recommended that hepatic function be assessed with laboratory tests before beginning atorvastatin treatment and repeated as clinically indicated thereafter. If evidence of serious liver injury occurs while a patient is taking atorvastatin, it should be discontinued and not restarted until the etiology of the patient’s liver dysfunction is defined. If no other cause is found, atorvastatin should be discontinued permanently.
The following have been shown to occur in 1–10% of patients taking atorvastatin in clinical trials:
High-dose atorvastatin have also been associated with worsening blood sugar control.
In 2014, the Food and Drug Administration (FDA) reported memory loss, forgetfulness and confusion with all statin products including atorvastatin. The symptoms were not serious, and they were rare and reversible on cessation of treatment with the medication.
Interactions with clofibrate, fenofibrate, gemfibrozil, which are fibrates used in accessory therapy in many forms of hypercholesterolemia, usually in combination with statins, increase the risk of myopathy and rhabdomyolysis.
Co-administration of atorvastatin with one of CYP3A4 inhibitors such as itraconazole,
Antacids can rarely decrease the plasma concentrations of statin medications, but do not affect the LDL-C -lowering efficacy.
Niacin also is proved to increase the risk of myopathy or rhabdomyolysis.
Some statins may also alter the concentrations of other medications, such as warfarin or digoxin, leading to alterations in effect or a requirement for clinical monitoring.
Vitamin D supplementation lowers atorvastatin and active metabolite concentrations, yet synergistically reduces LDL and total cholesterol concentrations. Grapefruit juice components are known inhibitors of intestinal CYP3A4.
Co-administration of grapefruit juice with atorvastatin may cause an increase in C max and AUC, which can lead to adverse reactions or overdose toxicity.
A few cases of myopathy have been reported when atorvastatin is given with colchicine.
Mechanism of action
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.
Recent studies have shown that in patients suffering from acute coronary syndrome, high-dose statin treatment may play a plaque-stabilizing role. At high doses, statins have anti-inflammatory effects, incite reduction of the necrotic plaque core, and improve endothelial function, leading to plaque stabilization and, sometimes, plaque regression. However, there is an increased risk of statin-associated adverse effects with such high-dose statin treatment.
The liver is the primary site of action of atorvastatin, as this is the principal site of both cholesterol synthesis and LDL clearance. It is the dosage of atorvastatin, rather than systemic medication concentration, which correlates with extent of LDL-C reduction.
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Atorvastatin undergoes rapid absorption when taken orally, with an approximate time to maximum plasma concentration ( T max ) of 1–2 h. The absolute bioavailability of the medication is about 14%, but the systemic availability for HMG-CoA reductase activity is approximately 30%. Atorvastatin undergoes high intestinal clearance and first-pass metabolism, which is the main cause for the low systemic availability. Administration of atorvastatin with food produces a 25% reduction in C max (rate of absorption) and a 9% reduction in AUC (extent of absorption), although food does not affect the plasma LDL-C -lowering efficacy of atorvastatin. Evening dose administration is known to reduce the C max and AUC by 30% each. However, time of administration does not affect the plasma LDL-C-lowering efficacy of atorvastatin.
The mean volume of distribution of atorvastatin is approximately 381 L. It is highly protein bound (≥98%), and studies have shown it is likely secreted into human breastmilk.
Atorvastatin metabolism is primarily through cytochrome P450 3A4 hydroxylation to form active ortho- and parahydroxylated metabolites, as well as various beta-oxidation metabolites. The ortho- and parahydroxylated metabolites are responsible for 70% of systemic HMG-CoA reductase activity. The ortho-hydroxy metabolite undergoes further metabolism via glucuronidation. As a substrate for the CYP3A4 isozyme, it has shown susceptibility to inhibitors and inducers of CYP3A4 to produce increased or decreased plasma concentrations, respectively. This interaction was tested in vitro with concurrent administration of erythromycin, a known CYP3A4 isozyme inhibitor, which resulted in increased plasma concentrations of atorvastatin. It is also an inhibitor of cytochrome 3A4.
Atorvastatin is primarily eliminated via hepatic biliary excretion, with less than 2% recovered in the urine. Bile elimination follows hepatic and/or extrahepatic metabolism. There does not appear to be any entero-hepatic recirculation. Atorvastatin has an approximate elimination half-life of 14 hours. Noteworthy, the HMG-CoA reductase inhibitory activity appears to have a half-life of 20–30 hours, which is thought to be due to the active metabolites. Atorvastatin is also a substrate of the intestinal P-glycoprotein efflux transporter, which pumps the medication back into the intestinal lumen during medication absorption.
In hepatic insufficiency, plasma concentrations of atorvastatin are significantly affected by concurrent liver disease. Patients with Child-Pugh Stage A liver disease show a four-fold increase in both C max and AUC. People with Child Pugh stage B liver disease show a 16-fold increase in C max and an 11-fold increase in AUC.
Geriatric patients (>65 years old) exhibit altered pharmacokinetics of atorvastatin compared to young adults, with mean AUC and C max values that are 40% and 30% higher, respectively. Additionally, healthy elderly patients show a greater pharmacodynamic response to atorvastatin at any dose; therefore, this population may have lower effective doses.
Several genetic polymorphisms have been found to be associated with a higher incidence of undesirable side effects of atorvastatin. This phenomenon is suspected to be related to increased plasma levels of pharmacologically active metabolites, such as atorvastatin lactone and p-hydroxyatorvastatin. Atorvastatin and its active metabolites may be monitored in potentially susceptible patients using specific chromatographic techniques.
Atorvastatin synthesis in commercial production (process) chemistry. The key step of establishing this medication’s stereocenters, through initial use of an inexpensive natural product ( chiral pool approach).
Atorvastatin synthesis during discovery chemistry. The key step of establishing stereocenters, using of a chiral ester auxiliary approach.
The first synthesis of atorvastatin at Parke-Davis that occurred during drug discovery was racemic followed by chiral chromatographic separation of the enantiomers. An early enantioselective route to atorvastatin made use of an ester chiral auxiliary to set the stereochemistry of the first of the two alcohol functional groups via a diastereoselective aldol reaction.
Once the compound entered pre-clinical development, process chemistry developed a cost-effective and scalable synthesis.
Bruce Roth, who was hired by Warner-Lambert as a chemist in 1982, had synthesized an “experimental compound” codenamed CI 981 – later called atorvastatin.
In 1994 the findings of a Merck-funded study were published in The Lancet concluding the efficacy of statins in lowering cholesterol in 4444 Scandinavian patients proving for the first time not only that a “statin reduced ‘bad’ LDL cholesterol but also that it led to a sharp drop in fatal heart attacks among patients with heart disease.”
In 1996 Warner-Lambert entered into a co-marketing agreement with Pfizer to sell Lipitor, and in 2000 Pfizer acquired Warner-Lambert for $90.2 billion.
Pfizer’s patent on atorvastatin expired in November 2011.
Pack and tablet of atorvastatin (Lipitor) 40mg
Atorvastatin calcium tablets are marketed by Pfizer under the trade name Lipitor
Pfizer’s US patent on Lipitor expired on 30 November 2011.
In other countries, atorvastatin calcium is made in tablet form by generic medication makers under various brand names including Stator, Atorvastatin Teva, Litorva, Torid, Atoris, Atorlip, Mactor, Lipvas, Sortis, Torvast, Torvacard, Totalip, and Tulip.
On 9 November 2012, Indian drugmaker Ranbaxy Laboratories Ltd. voluntarily recalled 10-, 20- and 40-mg doses of its generic version of atorvastatin in the United States.
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