fluvastatin

Ligand id: 2951

Name: fluvastatin

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: fluvastatin

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 82.69
Molecular weight 411.18
XLogP 4.96
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1993))
IUPAC Name
(3R,5S)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoic acid
International Nonproprietary Names
INN number INN
6547 fluvastatin
Synonyms
Canef® | Lescol®
Database Links
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
Search Google for chemicals with the same backbone FJLGEFLZQAZZCD
Search PubMed clinical trials fluvastatin
Search PubMed titles fluvastatin
Search PubMed titles/abstracts fluvastatin
Search UniChem for chemical match using the InChIKey FJLGEFLZQAZZCD-MCBHFWOFSA-N
Search UniChem for chemicals with the same backbone FJLGEFLZQAZZCD
Wikipedia Fluvastatin
Comments
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.