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
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
hydroxymethylglutaryl-CoA reductase Primary target of this compound Hs Inhibitor Competitive 8.2 pKi - 1
pKi 8.2 (Ki 5.7x10-9 M) [1]
Description: In vitro inhibition of HMG-CoA reductase
Conditions: pH 6.8, 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 8.4 pIC50 - 2
pIC50 8.4 (IC50 3.54x10-9 M) [2]
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 8.0 pIC50 - 3
pIC50 8.0 (IC50 1x10-8 M) [3]
Description: Inhibition of HMG-CoA reductase
Conditions: Inhibitory concentration against 3-hydroxy-3-methylglutaryl-CoA reductase (check paper for primary source )