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Compound Detail

CHEMBL1477

CERIVASTATIN
💊 Approved Drug
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💊 Approved Drug
COCc1c(C(C)C)nc(C(C)C)c(/C=C/[C@@H](O)C[C@@H](O)CC(=O)O)c1-c1ccc(F)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1477
Name CERIVASTATIN
Phase Approved
Structure Type MOL
InChI Key SEERZIQQUAZTOL-ANMDKAQQSA-N
Therapeutic ✓ Yes

Known Names

Cerivastatin Cerivastatina Cerivastatine Lipobay
5
Targets
18
Activities
1
Assay Types
20
PK Parameters
20
Publications
4
Known Names
1
Indications

Molecular Properties

459.6
MW (Da)
4.88
ALogP
5
HBA
3
HBD
99.9
PSA (Ų)
0.44
QED
0
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Withdrawn
USAN Stem -stat-
USAN Year 1996

Extended Properties

Molecular Formula C26H34FNO5
MW 459.56
Aromatic Rings 2
Heavy Atoms 33
NP-Likeness 0.33

Indications

Cardiovascular Diseases

ATC Classification

C10AA06
cerivastatin
Level 1: CARDIOVASCULAR SYSTEM
Level 2: LIPID MODIFYING AGENTS

Drug Warnings

Withdrawn
musculoskeletal toxicity
Increased reporting rate of rhabdomyolysis with Baycol relative to other statins, especially when gemfibrozil is co-prescribed
Country: Worldwide   Year: 2001
Withdrawn
General Warning
Increased reporting rate of rhabdomyolysis with Baycol relative to other statins, especially when gemfibrozil is co-prescribed
Country: Worldwide   Year: 2001
Withdrawn
General Warning
Severe muscle damage. Combination of cerivastatin and another cholesterol lowering drug, gemfibrozil, has caused severe damage to muscle in some patients. The damage can be in the form of rhabdomyolys...
Country: Worldwide   Year: 2001
Withdrawn
nephrotoxicity
Severe muscle damage. Combination of cerivastatin and another cholesterol lowering drug, gemfibrozil, has caused severe damage to muscle in some patients. The damage can be in the form of rhabdomyolys...
Country: Worldwide   Year: 2001
Withdrawn
musculoskeletal toxicity
Severe muscle damage. Combination of cerivastatin and another cholesterol lowering drug, gemfibrozil, has caused severe damage to muscle in some patients. The damage can be in the form of rhabdomyolys...
Country: Worldwide   Year: 2001

Activity Summary

IC50 18 meas. best 10.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3-hydroxy-3-methylglutaryl-coenzyme A reductase
CHEMBL402
 IC50 10.07 9.035 0.1 2
Hepatocyte
CHEMBL613362
 IC50 8.77 8.7375 1.7 4
L6
CHEMBL614793
 IC50 8.77 8.3975 1.7 4
3-hydroxy-3-methylglutaryl-coenzyme A reductase
CHEMBL3247
 IC50 8.55 8.37 2.8 3
HepG2
CHEMBL395
 IC50 6.89 6.34 130.0 5

Pharmacokinetic Data

Parameter Value Units Species
CL 2.9 mL.min-1.kg-1 Homo sapiens
CL 2.9 mL.min-1.kg-1 Homo sapiens
CL 2.9 mL.min-1.kg-1 Homo sapiens
CL 2.9 mL.min-1.kg-1 Homo sapiens
CL 10.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 10.72 uL.min-1.(10^6cells)-1 Homo sapiens
CL 43.0 mL.min-1.kg-1 Homo sapiens
CL 8.7 mL.min-1.kg-1 Rattus norvegicus
CL 19.7 mL.min-1.kg-1 Macaca fascicularis
CL 2.7 mL.min-1.kg-1 Homo sapiens
Cmax 25.0 nM Homo sapiens
F 60.0 % Homo sapiens
Fu 0.01 - Homo sapiens
Fu 0.01 - Homo sapiens
Fu 0.55 - Homo sapiens
Fu 0.000179 - Rattus norvegicus
Fu 0.000153 - Macaca fascicularis
Fu 0.000176 - Homo sapiens
MRT 1.8 hr Homo sapiens
T1/2 1.8 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 0.085 nM 10.07 DRUGMATRIX: HMG-CoA Reductase enzyme inhibition (substrate: [14C]HMG-CoA) -
Hepatocyte IC50 = 1.7 nM 8.77 Inhibition of cholesterol synthesis in rat liver hepatocytes after 4 hrs 17560788
Hepatocyte IC50 = 1.7 nM 8.77 Inhibition of cholesterol synthesis in rat hepatocytes 18072721
Hepatocyte IC50 = 1.7 nM 8.77 Inhibition of cholesterol synthesis in rat hepatocyte 18155906
L6 IC50 = 1.7 nM 8.77 Inhibition of cholesterol synthesis in rat L6 cells assessed as incorporation of... 18412317
Hepatocyte IC50 = 2.3 nM 8.64 Inhibition of cholesterol synthesis in rat hepatocytes assessed as incorporation... 18412317
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 2.8 nM 8.55 Inhibition of rat microsomal HMG-CoA reductase assessed as inhibition of cholest... 17560788
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 2.8 nM 8.55 Inhibition of HMG-CoA reductase in Sprague-Dawley rat liver microsomes 18072721
L6 IC50 = 3.0 nM 8.52 Inhibition of cholesterol synthesis in rat L6 cells 18072721
L6 IC50 = 7.0 nM 8.15 Inhibition of cholesterol synthesis in rat L6 cells after 3 hrs 17560788
L6 IC50 = 7.0 nM 8.15 Inhibition of cholesterol synthesis in rat L6 myocyte 18155906
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 9.8 nM 8.01 Inhibition of HMGR in rat hepatic microsomes assessed as conversion of [14C]HMG-... 18412317
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 10.0 nM 8.0 Inhibitory concentration against 3-hydroxy-3-methylglutaryl-CoA reductase 15686906
HepG2 IC50 = 130.0 nM 6.89 Cytotoxicity against human HepG2 cells assessed as reduction in nuclear size aft... 27105029
HepG2 IC50 = 340.0 nM 6.47 Cytotoxicity against human HepG2 cells assessed as increase in intracellular fre... 27105029
HepG2 IC50 = 600.0 nM 6.22 Cytotoxicity against human HepG2 cells assessed as reduction in mitochondrial me... 27105029
HepG2 IC50 = 800.0 nM 6.1 Cytotoxicity against human HepG2 cells assessed as increase in membrane permeabi... 27105029
HepG2 IC50 = 960.0 nM 6.02 Cytotoxicity against human HepG2 cells assessed as reduction in cell number afte... 27105029

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 617
27105029 10.1016/j.ejmech.2016.03.083 HepG2 20
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
32985885 10.1021/acs.jmedchem.0c01033 ADMET 11
21051535 10.1124/dmd.110.034629 ADMET 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
18412317 10.1021/jm800001n Cavia porcellus 7
- 10.6019/CHEMBL3301361 ADMET 4
18426954 10.1124/dmd.108.020479 ADMET 4
20014752 10.1021/tx900326k Hepatotoxicity 3
32985885 10.1021/acs.jmedchem.0c01033 No relevant target 3
18412317 10.1021/jm800001n Rattus norvegicus 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
18155906 10.1016/j.bmcl.2007.11.124 Hepatocyte 2
21601448 10.1016/j.bmcl.2011.04.133 No relevant target 2
17560788 10.1016/j.bmc.2007.05.031 L6 2
18412317 10.1021/jm800001n L6 2
18412317 10.1021/jm800001n No relevant target 2

Data from ChEMBL 36 via Core Engine