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 above) 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 above 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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2D Structure
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Physico-chemical Properties
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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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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1993))
IUPAC Name Click here for help
(3R,5S)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoic acid
International Nonproprietary Names Click here for help
INN number INN
6547 fluvastatin
Synonyms Click here for help
Canef® | Lescol®
Database Links Click here for help
CAS Registry No. 93957-54-1 (source: Scifinder)
ChEBI CHEBI:38561
ChEMBL Ligand CHEMBL1078
DrugBank Ligand DB01095
GtoPdb PubChem SID 135650279
PubChem CID 446155
RCSB PDB Ligand 115
Search Google for chemical match using the InChIKey FJLGEFLZQAZZCD-MCBHFWOFSA-N
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Search PubMed clinical trials fluvastatin
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Search UniChem for chemical match using the InChIKey FJLGEFLZQAZZCD-MCBHFWOFSA-N
Search UniChem for chemicals with the same backbone FJLGEFLZQAZZCD
Wikipedia Fluvastatin