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®.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: atorvastatin

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
CYP3A4 2
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
hydroxymethylglutaryl-CoA reductase Primary target of this compound Hs Inhibitor Competitive 7.8 pKi - 1
pKi 7.8 (Ki 1.4x10-8 M) [1]
Description: In vitro inhibition of HMG-CoA reductase
Conditions: pH 6.8, 37°C concentrations of substrates: 100µM HMG-CoA, 270µM NADPH. Human HMG-COA reductase catalytic domain was expressed in Escherichia coli BL(DE3) cells and purified using a GST affinity column.
hydroxymethylglutaryl-CoA reductase Rn Inhibitor Competitive 8.9 pIC50 - 5
pIC50 8.9 (IC50 1.16x10-9 M) [5]
Description: in vitro inhibition of cholesterol synthesis
Conditions: Inhibition IC50 values measured in primary rat hepatocytes
hydroxymethylglutaryl-CoA reductase Primary target of this compound Hs Inhibitor Competitive 8.1 pIC50 - 3
pIC50 8.1 (IC50 8x10-9 M) [3]
Targets where the ligand is described in the comment field
Target Comment