Atorvastatin

Atorvastatin

Clinical data
Pronunciation	/əˌtɔːrvəˈstætən/
Trade names	Lipitor, Atorva
AHFS/Drugs.com	Monograph
MedlinePlus	a600045
License data	US DailyMed: 42465
Pregnancy category	AU: D US: X (Contraindicated)
Routes of administration	By mouth
ATC code	C10AA05 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	12%
Metabolism	Hepatic (CYP3A4)
Biological half-life	14 hours
Excretion	Bile
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 Y
PubChem (CID)	60823
IUPHAR/BPS	2949
DrugBank	APRD00055 N
ChemSpider	54810 Y
UNII	A0JWA85V8F N
KEGG	D07474 Y
ChEBI	CHEBI:39548 Y
ChEMBL	CHEMBL1487 Y
PDB ligand ID	117 (PDBe, RCSB PDB)
ECHA InfoCard	100.125.464
Chemical and physical data
Formula	C33H35FN2O5
Molar mass	558.64
3D model (Jmol)	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 Y Key:XUKUURHRXDUEBC-KAYWLYCHSA-N Y

Atorvastatin, marketed under the trade name Lipitor among others, is a member of the drug 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 by a team led by Bruce Roth. From 1996 to 2012 under the trade name Lipitor, atorvastatin became the world's best-selling drug to that point, with more than US$125 billion in sales over approximately 14.5 years. In the UK atorvastatin costs about 2 pounds per month as of 2016.

The primary uses of atorvastatin is for the treatment of dyslipidemia and the prevention of cardiovascular disease:

There have been recent studies suggesting that high-dose statin therapy plays a plaque-stabilizing role in patients 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 drug treatment with certain other cholesterol-lowering drugs, 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.