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
No information available.
Summary of Clinical Use
Used in the treatment of hypercholesterolemia and reduction of the risk of cardiovascular disease.
Mechanism Of Action and Pharmacodynamic Effects
Competitive inhibitor of 3-hydroxy-3-methylglutaryl (HMG) coenzyme A reductase (HMG-CoA reductase), the enzyme catalysing the rate-limiting step of cholesterol synthesis. Acting primarily in the liver, simvastatin decreases hepatic cholesterol concentrations. For a complete overview of the mechanism of action of this drug, please see the entry on DrugBank linked to from this ligand page.
External links