simvastatin   

GtoPdb Ligand ID: 2955

Synonyms: MK-733 | Zocor®
simvastatin is an approved drug (FDA (1991), EMA (2013))
Compound class: Synthetic organic
Comment: Simvastatin is a statin class anti-dyslipidemia drug. It is synthetically derived from a fermantation product from Aspergillus terreus.
Simvastatin is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 72.83
Molecular weight 418.27
XLogP 4.78
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCC(C(=O)OC1CC(C)C=C2C1C(CCC1CC(O)CC(=O)O1)C(C=C2)C)(C)C
Isomeric SMILES CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)(C)C
InChI InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
InChI Key RYMZZMVNJRMUDD-HGQWONQESA-N
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 Hs Inhibitor Competitive 7.9 – 8.0 pIC50 - 1,3
pIC50 8.0 (IC50 1.1x10-8 M) [3]
pIC50 7.9 (IC50 1.21x10-8 M) [1]
Description: In vitro inhibition of HMG-CoA reductase
hydroxymethylglutaryl-CoA reductase Rn Inhibitor Competitive 6.8 – 9.1 pIC50 - 2,4-5
pIC50 9.1 (IC50 9x10-10 M) [2]
Description: Inhibition of HMG-CoA reductase
Conditions: Concentration of substrate:12.5 µM HMG-CoA. Inhibition of solubilized, purified rat liver HMG-CoA reductase.
pIC50 8.9 (IC50 1.3x10-9 M) [5]
Description: In vitro inhibition of cellular cholesterol synthesis
Conditions: Assay measuring sterol biosynthesis (cell assay) in rat hepatocytes at 37°C
pIC50 8.6 (IC50 2.74x10-9 M) [4]
Description: in vitro inhibition of cholesterol synthesis
Conditions: Inhibition IC50 values measured in primary rat hepatocytes
pIC50 7.3 (IC50 4.9x10-8 M) [5]
Description: In vitro inhibition of HMG-CoA reductase
Conditions: Assay using purified enzyme, 37oC
pIC50 6.8 (IC50 1.5x10-7 M) [5]
Description: In vitro inhibition of cellular cholesterol synthesis
Conditions: Assay measuring sterol biosynthesis (cell assay) in rat myocytes at 37°C