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Details

Stereochemistry RACEMIC
Molecular Formula C24H26FNO4
Molecular Weight 411.4659
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FLUVASTATIN

SMILES

CC(C)N1C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)=C(C2=C1C=CC=C2)C3=CC=C(F)C=C3

InChI

InChIKey=FJLGEFLZQAZZCD-JUFISIKESA-N
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-/m0/s1

HIDE SMILES / InChI

Description

Fluvastatin is an antilipemic agent that competitively inhibits hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase. Fluvastatin is marketed under the trade names Lescol, Canef, Vastin. LESCOL/LESCOL XL is an HMG-CoA reductase inhibitor (statin) indicated as an adjunctive therapy to diet to: Reduce elevated TC, LDL-C, Apo B, and TG, and to increase HDL-C in adult patients with primary hypercholesterolemia and mixed dyslipidemia Reduce elevated TC, LDL-C, and Apo B levels in boys and post-menarchal girls, 10 to 16 years of age, with heterozygous familial hypercholesterolemia after failing an adequate trial of diet therapy Reduce the risk of undergoing revascularization procedures in patients with clinically evident CHD Slow the progression of atherosclerosis in patients with CHD. Fluvastatin selectively and competitively inhibits the hepatic enzyme hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase. HMG-CoA reductase is responsible for converting HMG-CoA to mevalonate, the rate-limiting step in cholesterol biosynthesis. Inhibition results in a decrease in hepatic cholesterol levels which stimulates the synthesis of LDL receptors and increases hepatic uptake of LDL cholesterol. The end result is decreased levels of plasma total and LDL cholesterol.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
HMG-CoA reductase inhibitors: design, synthesis, and biological activity of tetrahydroindazole-substituted 3,5-dihydroxy-6-heptenoic acid sodium salts.
1993 Nov 12
Treatment of primary hypercholesterolemia: fluvastatin versus bezafibrate.
1994 Jun 6
Efficacy and safety of a combination fluvastatin-bezafibrate treatment for familial hypercholesterolemia: comparative analysis with a fluvastatin-cholestyramine combination.
1994 May
Currently available hypolipidaemic drugs and future therapeutic developments.
1995 Oct
Fluvastatin in combination with other lipid-lowering agents.
1996 Jan
Effect of fluvastatin or bezafibrate on the distribution of high density lipoprotein subpopulations in patients with familial hypercholesterolemia.
1996 Sep
A head-to-head comparison of the cost effectiveness of HMG-CoA reductase inhibitors and fibrates in different types of primary hyperlipidemia.
1997 Jan
Troglitazone upregulates LDL receptor activity in HepG2 cells.
1998 Aug
Postural hypotension induced by paroxetine.
1998 Feb 21
[Cardiology in 1997].
1998 Oct 5
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Hyperlipidemia Immediate Release Capsules: -Low-density lipoprotein cholesterol (LDL-C) reduction to a goal of 25% or greater: Initial dose of 40 mg orally once a day in the evening or 40 mg orally twice a day -LDL-C reduction to a goal of less than 25%: Initial dose of 20 mg orally once a day -Maintenance dose: 20 mg to 80 mg per day Usual Adult Dose for Hyperlipoproteinemia Type IIa (Elevated LDL) Immediate Release Capsules: -Low-density lipoprotein cholesterol (LDL-C) reduction to a goal of 25% or greater: Initial dose of 40 mg orally once a day in the evening or 40 mg orally twice a day -LDL-C reduction to a goal of less than 25%: Initial dose of 20 mg orally once a day -Maintenance dose: 20 mg to 80 mg per day
Route of Administration: Oral
In Vitro Use Guide
Fluvastatin markedly inhibits the formation of thiobarbituric acid reactive substances in iron (II)-supported peroxidation of liposomes with IC50 of 12 uM. Fluvastatin ranging from 1 uM to 100 uM inhibits peroxyl radical-mediated peroxidation of liposomes induced by water-soluble and lipid-soluble radical generators, 2,2'-azobis (2-amidinopropane) dihydro-chloride and 2,2'-azobis (2,4-dimethylvaleronitrile), respectively.
Name Type Language
FLUVASTATIN
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
FLUVASTATIN [WHO-DD]
Common Name English
FLUVASTATIN [VANDF]
Common Name English
FLUVASTATIN [MI]
Common Name English
FLUVAS
Brand Name English
FLUVASTATIN [INN]
Common Name English
6-HEPTENOIC ACID, 7-(3-(4-FLUOROPHENYL)-1-(1-METHYLETHYL)-1H-INDOL-2-YL)-3,5-DIHYDROXY-, (3R,5S,6E)-REL-
Systematic Name English
Classification Tree Code System Code
WHO-VATC QC10AA04
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
NDF-RT N0000175589
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
LIVERTOX 430
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
NDF-RT N0000000121
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
WHO-ATC C10AA04
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
Code System Code Type Description
PUBCHEM
1548972
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY SWITZERF
NCI_THESAURUS
C61768
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
RXCUI
41127
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY RxNorm
ChEMBL
CHEMBL2220442
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
IUPHAR
2951
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
MESH
C065180
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
INN
6547
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
HSDB
93957-54-1
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
LactMed
93957-54-1
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
EVMPD
SUB07768MIG
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
DRUG BANK
DB01095
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
EPA CompTox
93957-54-1
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
CAS
93957-54-1
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY
MERCK INDEX
M5515
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY Merck Index
WIKIPEDIA
FLUVASTATIN
Created by admin on Tue Mar 06 11:20:02 UTC 2018 , Edited by admin on Tue Mar 06 11:20:02 UTC 2018
PRIMARY