lovastatin   

GtoPdb Ligand ID: 2739

Synonyms: (+)-mevinolin | 6α-methylcompactin | Mevacor®
lovastatin is an approved drug (FDA (1987))
Comment: Lovastatin is a 3-hydroxy-3-methylglutaryl-CoA reductase (HMG-CoA) inhibitor; a statin drug used for the prevention of cardiovascular diseases.
NB: there may be ambiguity in the chiral specification in the reported literature, compared to the structure represented here.
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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 404.26
XLogP 4.57
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
Isomeric SMILES CC[C@@H](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
InChI InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
InChI Key PCZOHLXUXFIOCF-BXMDZJJMSA-N
No information available.
Summary of Clinical Use
One of the statin group of drugs, used in the treatment of hypercholesterolemia and mixed dyslipidemia.
Mechanism Of Action and Pharmacodynamic Effects
Competitive inhibitor of HMG-CoA reductase, the enzyme catalysing the rate-limiting step of cholesterol synthesis. Acting primarily in the liver, lovastatin 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