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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: fluvastatin

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
1. Boralli VB, Coelho EB, Sampaio SA, Marques MP, Lanchote VL. (2009)
Enantioselectivity in the pharmacokinetic interaction between fluvastatin and lercanidipine in healthy volunteers.
J Clin Pharmacol, 49 (2): 205-11. [PMID:19033449]
2. Carbonell T, Freire E. (2005)
Binding thermodynamics of statins to HMG-CoA reductase.
Biochemistry, 44 (35): 11741-8. [PMID:16128575]
3. Connolly PJ, Westin CD, Loughney DA, Minor LK. (1993)
HMG-CoA reductase inhibitors: design, synthesis, and biological activity of tetrahydroindazole-substituted 3,5-dihydroxy-6-heptenoic acid sodium salts.
J Med Chem, 36 (23): 3674-85. [PMID:8246237]
4. Di Pietro G, Coelho EB, Geleilete TM, Marques MP, Lanchote VL. (2006)
Chiral evaluation of fluvastatin in human plasma by high-performance liquid chromatography electrospray mass spectrometry.
J Chromatogr B Analyt Technol Biomed Life Sci, 832 (2): 256-61. [PMID:16480934]
5. Holdgate GA, Ward WH, McTaggart F. (2003)
Molecular mechanism for inhibition of 3-hydroxy-3-methylglutaryl CoA (HMG-CoA) reductase by rosuvastatin.
Biochem Soc Trans, 31 (Pt 3): 528-31. [PMID:12773150]
6. Hosoda S, Matsuda D, Tomoda H, Hashimoto M, Aoyama H, Hashimoto Y. (2009)
Application of a 3,3-diphenylpentane skeleton as a multi-template for creation of HMG-CoA reductase inhibitors.
Bioorg Med Chem Lett, 19 (15): 4228-31. [PMID:19502059]
7. Istvan ES, Deisenhofer J. (2001)
Structural mechanism for statin inhibition of HMG-CoA reductase.
Science, 292 (5519): 1160-4. [PMID:11349148]
8. Jendralla H, Granzer E, von Kerekjarto B, Krause R, Schacht U, Baader E, Bartmann W, Beck G, Bergmann A, Kesseler K. (1991)
Synthesis and biological activity of new HMG-CoA reductase inhibitors. 3. Lactones of 6-phenoxy-3,5-dihydroxyhexanoic acids.
J Med Chem, 34 (10): 2962-83. [PMID:1656041]
9. McTaggart F, Buckett L, Davidson R, Holdgate G, McCormick A, Schneck D, Smith G, Warwick M. (2001)
Preclinical and clinical pharmacology of Rosuvastatin, a new 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor.
Am J Cardiol, 87 (5A): 28B-32B. [PMID:11256847]