fluvastatin   Click here for help

GtoPdb Ligand ID: 2951

Synonyms: Canef® | Lescol®
Approved drug PDB Ligand
fluvastatin is an approved drug (FDA (1993))
Compound class: Synthetic organic
Comment: Fluvastatin is a member of the cholesterol-lowering statin family of drugs. The approved drug is a racemic mixture of a 3R, 5S isomer and a 3S, 5R isomer, and this is supported by the INN document which also indicates a racemate. The 3R, 5S isomer (shown here, and in the PubChem link below) is more pharmacologically active [1,4]. The other isomer is represented by CID 1548972. Representations of the stereochemistry of fluvastatin shown on the resources linked to below may vary from the structure shown here. The majority of the references we cite for our biological activity data do not specify whether the racemate or a specific stereoisomer were used in their experiments.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: fluvastatin

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 82.69
Molecular weight 411.18
XLogP 4.51
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC(=O)CC(CC(C=Cc1c(c2ccc(cc2)F)c2c(n1C(C)C)cccc2)O)O
Isomeric SMILES OC(=O)C[C@@H](C[C@@H](/C=C/c1c(c2ccc(cc2)F)c2c(n1C(C)C)cccc2)O)O
InChI InChI=1S/C24H26FNO4/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30)/b12-11+/t18-,19-/m1/s1
InChI Key FJLGEFLZQAZZCD-MCBHFWOFSA-N
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
hydroxymethylglutaryl-CoA reductase Primary target of this compound Hs Inhibitor Competitive 6.6 – 7.6 pKi - 2,5
⤷ pKi 7.6 (Ki 2.8x10-8 M) [5]
pKi 6.6 (Ki 2.56x10-7 M) [2]
Description: In vitro inhibition of HMG-CoA reductase
Conditions: 100µM HMG-CoA and 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 – 8.6 pIC50 - 3,6,8-9
⤷ pIC50 8.6 (IC50 2.5x10-9 M) [3]
Description: In vitro inhibition of HMG-CoA reductase
Conditions: Substrate concentrations: 2.8mM NADPH, 0.1 mM HMG-CoA. Partially purified microsomal preparations
pIC50 8.6 (IC50 2.5x10-9 M) [8]
Description: In vitro inhibition of HMG-CoA reductase
Conditions: Crude rat liver (solubilized enzyme )
pIC50 8.5 (IC50 3x10-9 M) [6]
Description: in vitro inhibition of HMG-CoA reductase
Conditions: DL-[3-14C]3-hydroxy-3-methylglutaryl-CoA (0.37 MBq) and 10 mg protein of microsomal fraction incubated at 37°C for 30 min The reaction was terminated by addition of 2 M HCl aq and the metabolites were converted to mevalonolactone. The metabolite mixture was separated by means of thin layer chromatography (Merck 20 TLC plates Silica Gel 60 F254) with acetone/benzene (1:1 v/v). The radioactivity of each spot on the plate was measured with a bioimaging analyzer (FLA-7000, Fuji Film, Japan).
pIC50 8.4 (IC50 3.78x10-9 M) [9]
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 7.6 pIC50 - 7
⤷ pIC50 7.6 (IC50 2.8x10-8 M) [7]
Description: Inhibition of HMG-CoA reductase