cerivastatin   Click here for help

GtoPdb Ligand ID: 2950

Synonyms: Baycol® | Lipobay®
Approved drug
cerivastatin is an approved drug (FDA (1997))
Compound class: Synthetic organic
Comment: Cerivastatin is a cholesterol-lowering drug.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 99.88
Molecular weight 459.24
XLogP 3.42
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COCc1c(c2ccc(cc2)F)c(C=CC(CC(CC(=O)O)O)O)c(nc1C(C)C)C(C)C
Isomeric SMILES COCc1c(c2ccc(cc2)F)c(/C=C/[C@H](C[C@H](CC(=O)O)O)O)c(nc1C(C)C)C(C)C
InChI InChI=1S/C26H34FNO5/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32)/b11-10+/t19-,20-/m1/s1
InChI Key SEERZIQQUAZTOL-ANMDKAQQSA-N
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Summary of Clinical Use Click here for help
Cerivastatin was used to reduce circulating levels of LDL and total cholesterol, but was withdrawn from the US market as a result of severe/fatal adverse effects.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Cerivastatin reduces cholesterol and LDL levels by inhibiting the hepatic production of the sterol precursor mevalonate, via inhibition hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase, the enzyme responsible for conversion of HMG-CoA to mevalonate.