atorvastatin   Click here for help

GtoPdb Ligand ID: 2949

Synonyms: Lipitor®
Approved drug PDB Ligand
atorvastatin is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: The 3S, 5S-Atorvastatin enantiomer is inactive [4]. Atorvastatin is metabolised to form active metabolites atorvastatin lactone (CID 6483036), o-hydroxyatorvastatin (CID 9808225) and p-hydroxyatorvastatin (CID 9851106).

Atorvastatin calcium is found in combination with amlodipine besylate in the drug Caduet®.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 13
Topological polar surface area 111.79
Molecular weight 558.25
XLogP 5.68
No. Lipinski's rules broken 2
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Canonical SMILES OC(CC(CC(=O)O)O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1
Isomeric SMILES O[C@@H](C[C@H](CC(=O)O)O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1
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
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Summary of Clinical Use Click here for help
Cholesterol-lowering drug used to treat hypercholesterolaemia and mixed lipidemia, and as a primary preventative medication for patients with multiple risk factors for coronary heart disease. Atorvastatin is a component of the fixed-ratio drug Caduet® (marketed as Envacar® in some countries) which also contains the calcium channel blocker amlodipine. Caduet® was first approved by the US FDA in 2004.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Atorvastatin is a competitive inhibitor of hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase, the rate-determining enzyme in cholesterol biosynthesis via the mevalonate pathway.