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Compound Detail

CHEMBL2220442

FLUVASTATIN
💊 Approved Drug
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💊 Approved Drug
CC(C)n1c(/C=C/C(O)CC(O)CC(=O)O)c(-c2ccc(F)cc2)c2ccccc21

Basic Information

ChEMBL ID CHEMBL2220442
Name FLUVASTATIN
Phase Approved
Structure Type MOL
InChI Key FJLGEFLZQAZZCD-VAWYXSNFSA-N
Therapeutic ✓ Yes

Known Names

Fluvas Fluvastatin Fluvastatina Fluvastatine NSC-758896
11
Targets
16
Activities
3
Assay Types
23
PK Parameters
20
Publications
5
Known Names
12
Indications

Molecular Properties

411.5
MW (Da)
4.63
ALogP
4
HBA
3
HBD
82.7
PSA (Ų)
0.50
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1993
Availability Prescription
Chirality Racemic

Routes of Administration

Oral
USAN Stem -stat-
USAN Year 1989

Extended Properties

Molecular Formula C24H26FNO4
MW 411.47
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness 0.03

Indications

Cardiovascular Diseases Erectile Dysfunction Hypercholesterolemia Lipid Metabolism Disorders Aortic Valve Stenosis Hepatitis C Hepatitis C, Chronic Nephritis, Hereditary Polyendocrinopathies, Autoimmune Prostatic Neoplasms, Castration-Resistant Paraganglioma Melanoma

ATC Classification

C10AA04
fluvastatin
Level 1: CARDIOVASCULAR SYSTEM
Level 2: LIPID MODIFYING AGENTS

Activity Summary

IC50 10 meas. best 9.45
EC50 5 meas. best 5.74
Kd 1 meas. best 4.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3-hydroxy-3-methylglutaryl-coenzyme A reductase
CHEMBL402
IC50 9.45 8.5 0.4 2
3-hydroxy-3-methylglutaryl-coenzyme A reductase
CHEMBL3247
IC50 8.52 8.52 3.0 1
HepG2
CHEMBL395
IC50 7.55 7.55 28.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 6.4 6.4 400.0 1
dengue virus type 2
CHEMBL613966
EC50 5.74 5.74 1820.0 1
Nuclear receptor subfamily 4 group A member 2
CHEMBL5002
EC50 5.72 5.72 1900.0 3
NAD-dependent protein deacylase sirtuin-6
CHEMBL2163182
EC50 5.15 5.15 7100.0 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
Kd 4.96 4.96 11040.0 1
Bile salt export pump
CHEMBL6020
IC50 4.44 4.44 36100.0 3
Hepatic sodium/bile acid cotransporter
CHEMBL5287
IC50 4.4 4.4 40000.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
IC50 4.24 4.24 57000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 614.74 ng.hr.mL-1 Homo sapiens
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Canis lupus familiaris
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 32.0 mL.min-1.kg-1 Rattus norvegicus
CL 35.0 mL.min-1.kg-1 Macaca
CL 8.33 mL.min-1.g-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 4.3 mL.min-1.kg-1 Rattus norvegicus
CL 7.3 mL.min-1.kg-1 Homo sapiens
Cmax 663.0 nM Homo sapiens
F 49.0 % Homo sapiens
F 24.0 % Homo sapiens
F 95.0 % Homo sapiens
Fu 0.0079 - Homo sapiens
Fu 0.0079 - Homo sapiens
Fu 9e-05 - Rattus norvegicus
Fu 9.22e-05 - Homo sapiens
MRT 0.44 hr Homo sapiens
T1/2 0.7 hr Homo sapiens
Vd 0.35 L.kg-1 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 = 0.353 nM 9.45 DRUGMATRIX: HMG-CoA Reductase enzyme inhibition (substrate: [14C]HMG-CoA) -
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 3.0 nM 8.52 Inhibition of rat HMG-CoA reductase using 0.37 MBq DL-[3-14C]HMG-CoA 19502059
HepG2 IC50 = 28.0 nM 7.55 In vitro inhibitory activity was evaluated on cholesterol biosynthesis in HepG2 ... 14741258
3-hydroxy-3-methylglutaryl-coenzyme A reductase IC50 = 28.0 nM 7.55 Inhibitory concentration against 3-hydroxy-3-methylglutaryl-CoA reductase 15686906
Cytochrome P450 2C9 IC50 = 400.0 nM 6.4 DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
dengue virus type 2 EC50 = 1820.0 nM 5.74 Antiviral activity against Dengue virus 2 NGC infected in human A549 cells asses... 26771861
Nuclear receptor subfamily 4 group A member 2 EC50 = 1900.0 nM 5.72 Agonist activity at human Nurr1 measured by Gal4-Nurr1 hybrid reporter gene assa... 35797147
Nuclear receptor subfamily 4 group A member 2 EC50 = 1900.0 nM 5.72 Agonist activity at human Nurr1 transfected in HEK293T cells co-transfected with... 37256819
Nuclear receptor subfamily 4 group A member 2 EC50 = 1900.0 nM 5.72 Agonist activity at Gal4-fused human full length Nurr1 transfected in human HEK2... 37751901
NAD-dependent protein deacylase sirtuin-6 EC50 = 7100.0 nM 5.15 Activation of recombinant SIRT6 (unknown origin) using fluoro substrate peptide ... 33214841
Retinoic acid receptor RXR-alpha Kd = 11040.0 nM 4.96 Binding affinity to RXRalpha-LBD (unknown origin) measured up to 120 sec by surf... 28089347
Bile salt export pump IC50 = 36100.0 nM 4.44 Inhibition of human BSEP expressed in fall armyworm sf9 cell plasma membrane ves... 20829430
Bile salt export pump IC50 = 36100.0 nM 4.44 Inhibition of recombinant human BSEP expressed in baculovirus infected sf9 cell ... 24799086
Bile salt export pump IC50 = 36100.0 nM 4.44 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Hepatic sodium/bile acid cotransporter IC50 = 40000.0 nM 4.4 Inhibition of human recombinant NTCP expressed in CHO cells assessed as reductio... 31439379
ATP-binding cassette sub-family C member 3 IC50 = 57000.0 nM 4.24 Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles asse... 23956101

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 638
21051535 10.1124/dmd.110.034629 ADMET 21
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15920768 10.1002/jps.20373 ADMET 8
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
33214841 10.1021/acsmedchemlett.0c00407 NAD-dependent protein deacylase sirtuin-6 7
32985885 10.1021/acs.jmedchem.0c01033 ADMET 7
20081855 10.1038/nchembio.301 RD 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 5
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL3301361 ADMET 4
18779350 10.1128/aac.00513-08 Plasmodium falciparum 4
16019946 10.1080/00498250400028197 ADMET 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 4
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4

Data from ChEMBL 36 via Core Engine