Identification

Name
Fluvastatin
Accession Number
DB01095  (APRD00346)
Type
Small Molecule
Groups
Approved
Description

Fluvastatin is an antilipemic agent that competitively inhibits hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase. HMG-CoA reductase catalyzes the conversion of HMG-CoA to mevalonic acid, the rate-limiting step in cholesterol biosynthesis. Fluvastatin belongs to a class of medications called statins and is used to reduce plasma cholesterol levels and prevent cardiovascular disease. It is also the first entirely synthetic HMG-CoA reductase inhibitor and is structurally distinct from the fungal derivatives of this therapeutic class. Fluvastatin is a racemate comprising equimolar amounts of (3R,5S)- and (3S,5R)-fluvastatin.

Structure
Thumb
Synonyms
  • fluvastatina
  • fluvastatine
  • fluvastatinum
Product Ingredients
IngredientUNIICASInChI Key
Fluvastatin sodiumPYF7O1FV7F93957-55-2ZGGHKIMDNBDHJB-NRFPMOEYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LescolCapsule40 mg/1OralPhysicians Total Care, Inc.2002-03-08Not applicableUs
LescolCapsule20 mg/1OralNovartis1993-12-302017-07-10Us00078 0176 15 nlmimage10 b80edc36
LescolCapsule20 mg/1OralPhysicians Total Care, Inc.1994-06-10Not applicableUs
LescolCapsule40 mg/1OralNovartis1993-12-302017-07-10Us
Lescol 20mgCapsule20 mgOralNovartis1994-12-31Not applicableCanada
Lescol 40mgCapsule40 mgOralNovartis1994-12-31Not applicableCanada
Lescol XLTablet, extended release80 mg/1OralNovartis2000-10-06Not applicableUs00078 0354 05 nlmimage10 37091bf8
Lescol XLTablet, extended release80 mgOralNovartis2004-04-05Not applicableCanada
Lescol XLTablet, extended release80 mg/1OralCarilion Materials Management2000-10-06Not applicableUs
Lescol XLTablet, extended release80 mg/1OralPhysicians Total Care, Inc.2002-03-12Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FluvastatinCapsule20 mg/1OralTeva2012-07-05Not applicableUs00093 7442 56 nlmimage10 30271848
FluvastatinCapsule40 mg/1OralTeva2012-07-05Not applicableUs00093 7443 56 nlmimage10 052702b8
Fluvastatin SodiumCapsule20 mg/1OralMylan Pharmaceuticals2013-03-19Not applicableUs
Fluvastatin SodiumCapsule40 mg/1OralCarilion Materials Management2013-03-19Not applicableUs
Fluvastatin SodiumTablet, film coated, extended release80 mg/1OralTeva2016-06-02Not applicableUs
Fluvastatin SodiumTablet, film coated, extended release80 mg/1OralMylan Pharmaceuticals2015-09-11Not applicableUs
Fluvastatin SodiumCapsule40 mg/1OralMylan Pharmaceuticals2013-03-19Not applicableUs00378 8021 93 nlmimage10 043b0218
Fluvastatin SodiumCapsule20 mg/1OralCarilion Materials Management2013-03-19Not applicableUs00378 8020 77 nlmimage10 043b0248
Fluvastatin Sodium ERTablet, extended release80 mg/1OralSandoz2015-10-16Not applicableUs
Fluvastatin Sodium ERTablet, extended release80 mg/1OralSandoz2015-10-16Not applicableUs
International/Other Brands
Canef (AstraZeneca) / Cranoc (Astellas)
Categories
UNII
4L066368AS
CAS number
93957-54-1
Weight
Average: 411.4659
Monoisotopic: 411.18458653
Chemical Formula
C24H26FNO4
InChI Key
FJLGEFLZQAZZCD-JUFISIKESA-N
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-/m0/s1
IUPAC Name
(3S,5R,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
SMILES
CC(C)N1C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C12

Pharmacology

Indication

To be used as an adjunct to dietary therapy to prevent cardiovascular events. May be used as secondary prevention in patients with coronary heart disease (CHD) to reduce the risk of requiring coronary revascularization procedures, for reducing progression of coronary atherosclerosis in hypercholesterolemic patients with CHD, and for the treatment of primary hypercholesterolemia and mixed dyslidipidemia.

Associated Conditions
Pharmacodynamics

Fluvastatin, the first synthetically-derived HMG-CoA reductase inhibitor, is a hydrophilic, acidic, antilipemic agent used to lower cholesterol and triglyceride levels associated with primary hypercholesterolemia and mixed dyslipidemia (Fredrickson types IIa and IIb), to slow the progression of coronary atherosclerosis in patients with CHD and as secondary prevention therapy in patients with CHD to reduce the risk of requiring coronary revascularization procedures. Although similar to lovastatin, simvastatin, and pravastatin, fluvastatin has a shorter half-life, no active metabolites, extensive protein binding, and minimal CSF penetration. Fluvastatin acts primarily in the liver. It is prepared as a racemate of two erythro enantiomers of which the 3R,5S enantiomer exerts the pharmacologic effect.

Mechanism of action

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.

TargetActionsOrganism
A3-hydroxy-3-methylglutaryl-coenzyme A reductase
inhibitor
Human
Absorption

Rapidly and almost completely absorbed (> 90%), but undergoes extensive first pass metabolism. Bioavailability is 24% (range 9-50%) when a 10 mg dose is given. The mean relative bioavailability of the extended-release tablet is 29% (range: 9% to 66%) compared to an immediate-release capsule administered under fasting conditions. When given orally, fluvastatin reaches peak concentrations (Tmax) in less than one hour. Taking the extended release tablet with a high-fat meal will delay absorption (Tmax = 6 hours) and increase bioavailability by approximately 50%. However, the maximum concentration of fluvastatin sodium extended-release tablets seen after a high fat meal is less than the peak concentration following a single dose or twice daily dose of the 40 mg fluvastatin capsule.

Volume of distribution
  • 0.35 L/kg
Protein binding

98% bound to plasma proteins. At therapeutic concentrations, the protein binding of fluvastatin is not affected by warfarin, salicylic acid and glyburide.

Metabolism

Undergoes hepatic metabolism primarily via hydroxylation of the indole ring at the 5- and 6-positions to 5-hydroxy fluvastatin and 6-hydroxy fluvastatin, respectively. N-dealkylation to N-desisopropyl fluvastatin and beta-oxidation of the side chain also occurs. Metabolized primarily by the CYP2C9 isozyme system (75%), and to a lesser extent by CYP3A4 (~20%) and CYP2C8 (~5%). Hydroxylated metabolites retain some pharmcological activity, but are present as conjugates (glucuronides and sulfates) in the blood and are rapidly eliminated via bile into feces. Both enantiomers of fluvastatin are metabolized in a similar manner. Fluvastatin also undergoes glucuronidation via UGT enzymes.

Route of elimination

When orally administered, fluvastatin is primarily excreted in the faces ( ~90%) as metabolites, with less than 2% present as unchanged drug. Approximately 5% was recovered in the urine.

Half life

3 hours

Clearance
  • 0.8 L/h/kg
  • 107 ± 38.1 L/h [Hypercholesterolemia patients receiving a single dose of 20 mg]
  • 87.8 ± 45 L/h [Hypercholesterolemia patients receiving 20 mg twice daily]
  • 108 ± 44.7 L/h [Hypercholesterolemia patients receiving 40 mg single]
  • 64.2 ± 21.1 L/h [Hypercholesterolemia patients receiving 40 mg twice daily]
Toxicity

Generally well-tolerated. May cause gastrointestinal upset (diarrhea, nausea, constipation, gas, abdominal pain), myotoxicity (mypothy, myositis, rhabdomyolysis), and hepatotoxicity.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Fluvastatin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Fluvastatin.Experimental
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Fluvastatin.Experimental, Investigational
4-hydroxycoumarinThe serum concentration of 4-hydroxycoumarin can be increased when it is combined with Fluvastatin.Experimental
AbirateroneThe metabolism of Fluvastatin can be decreased when combined with Abiraterone.Approved
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Fluvastatin.Approved, Investigational
AcetylcysteineThe excretion of Fluvastatin can be decreased when combined with Acetylcysteine.Approved, Investigational
AcipimoxAcipimox may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved, Investigational
Alendronic acidThe risk or severity of myopathy and rhabdomyolysis can be increased when Alendronic acid is combined with Fluvastatin.Approved
Aluminium clofibrateThe risk or severity of myopathy and rhabdomyolysis can be increased when Aluminium clofibrate is combined with Fluvastatin.Experimental
Aminohippuric acidThe excretion of Fluvastatin can be decreased when combined with Aminohippuric acid.Approved, Investigational
AmiodaroneThe risk or severity of myopathy and rhabdomyolysis can be increased when Amiodarone is combined with Fluvastatin.Approved, Investigational
Amphotericin BThe risk or severity of myopathy and rhabdomyolysis can be increased when Amphotericin B is combined with Fluvastatin.Approved, Investigational
AmprenavirThe metabolism of Fluvastatin can be decreased when combined with Amprenavir.Approved, Investigational
ApalutamideThe serum concentration of Fluvastatin can be decreased when it is combined with Apalutamide.Approved, Investigational
AprepitantThe serum concentration of Fluvastatin can be increased when it is combined with Aprepitant.Approved, Investigational
AsunaprevirThe excretion of Fluvastatin can be decreased when combined with Asunaprevir.Approved, Investigational, Withdrawn
AtazanavirThe metabolism of Fluvastatin can be decreased when combined with Atazanavir.Approved, Investigational
AtorvastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Fluvastatin is combined with Atorvastatin.Approved
AxitinibThe excretion of Fluvastatin can be decreased when combined with Axitinib.Approved, Investigational
BaclofenThe risk or severity of myopathy and rhabdomyolysis can be increased when Baclofen is combined with Fluvastatin.Approved
BenzbromaroneThe excretion of Fluvastatin can be decreased when combined with Benzbromarone.Investigational, Withdrawn
BetamethasoneThe risk or severity of myopathy and rhabdomyolysis can be increased when Betamethasone is combined with Fluvastatin.Approved, Vet Approved
BezafibrateBezafibrate may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved, Investigational
BicalutamideThe metabolism of Fluvastatin can be decreased when combined with Bicalutamide.Approved
BoceprevirThe metabolism of Fluvastatin can be decreased when combined with Boceprevir.Approved, Withdrawn
BosentanThe serum concentration of Fluvastatin can be decreased when it is combined with Bosentan.Approved, Investigational
BumetanideThe risk or severity of myopathy and rhabdomyolysis can be increased when Bumetanide is combined with Fluvastatin.Approved
CabazitaxelThe excretion of Fluvastatin can be decreased when combined with Cabazitaxel.Approved
CandesartanThe excretion of Fluvastatin can be decreased when combined with Candesartan.Experimental
CapecitabineThe metabolism of Fluvastatin can be decreased when combined with Capecitabine.Approved, Investigational
CaptoprilThe risk or severity of myopathy and rhabdomyolysis can be increased when Captopril is combined with Fluvastatin.Approved
CarbamazepineThe serum concentration of Fluvastatin can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarbimazoleThe risk or severity of myopathy and rhabdomyolysis can be increased when Carbimazole is combined with Fluvastatin.Approved, Investigational
CaspofunginThe excretion of Fluvastatin can be decreased when combined with Caspofungin.Approved
CeritinibThe serum concentration of Fluvastatin can be increased when it is combined with Ceritinib.Approved
CerivastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Fluvastatin is combined with Cerivastatin.Approved, Withdrawn
ChloroquineThe risk or severity of myopathy and rhabdomyolysis can be increased when Chloroquine is combined with Fluvastatin.Approved, Investigational, Vet Approved
CholecystokininThe excretion of Fluvastatin can be decreased when combined with Cholecystokinin.Approved, Investigational
CholestyramineThe serum concentration of Fluvastatin can be decreased when it is combined with Cholestyramine.Approved, Investigational
Cholic AcidThe excretion of Fluvastatin can be decreased when combined with Cholic Acid.Approved
CimetidineThe serum concentration of Fluvastatin can be increased when it is combined with Cimetidine.Approved, Investigational
CiprofibrateThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Ciprofibrate is combined with Fluvastatin.Approved, Investigational
CiprofloxacinThe risk or severity of myopathy and rhabdomyolysis can be increased when Ciprofloxacin is combined with Fluvastatin.Approved, Investigational
CladribineThe risk or severity of myopathy and rhabdomyolysis can be increased when Cladribine is combined with Fluvastatin.Approved, Investigational
ClarithromycinThe risk or severity of rhabdomyolysis can be increased when Clarithromycin is combined with Fluvastatin.Approved
ClofibrateThe risk or severity of myopathy and rhabdomyolysis can be increased when Clofibrate is combined with Fluvastatin.Approved, Investigational
ClofibrideThe risk or severity of myopathy and rhabdomyolysis can be increased when Clofibride is combined with Fluvastatin.Experimental
ClorindioneThe serum concentration of Clorindione can be increased when it is combined with Fluvastatin.Experimental
ClotrimazoleThe metabolism of Fluvastatin can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Fluvastatin can be decreased when combined with Cobicistat.Approved
ColchicineColchicine may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved
ColesevelamColesevelam can cause a decrease in the absorption of Fluvastatin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Fluvastatin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Fluvastatin.Approved, Investigational
Conjugated estrogensThe excretion of Fluvastatin can be decreased when combined with Conjugated estrogens.Approved
CrisaboroleThe metabolism of Fluvastatin can be decreased when combined with Crisaborole.Approved, Investigational
CrizotinibThe metabolism of Fluvastatin can be decreased when combined with Crizotinib.Approved
CurcuminThe metabolism of Fluvastatin can be decreased when combined with Curcumin.Approved, Investigational
CyclosporineThe serum concentration of Fluvastatin can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe metabolism of Fluvastatin can be decreased when combined with Cyproterone acetate.Approved, Investigational
CytarabineThe risk or severity of myopathy and rhabdomyolysis can be increased when Cytarabine is combined with Fluvastatin.Approved, Investigational
DabrafenibThe serum concentration of Fluvastatin can be decreased when it is combined with Dabrafenib.Approved, Investigational
DaclatasvirThe excretion of Fluvastatin can be decreased when combined with Daclatasvir.Approved, Investigational
DanazolThe serum concentration of Fluvastatin can be increased when it is combined with Danazol.Approved
DaptomycinThe risk or severity of myopathy can be increased when Fluvastatin is combined with Daptomycin.Approved, Investigational
DarunavirThe metabolism of Fluvastatin can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Fluvastatin can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Fluvastatin can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Fluvastatin can be decreased when combined with Delavirdine.Approved
DexamethasoneThe risk or severity of myopathy and rhabdomyolysis can be increased when Dexamethasone is combined with Fluvastatin.Approved, Investigational, Vet Approved
DiclofenacThe excretion of Fluvastatin can be decreased when combined with Diclofenac.Approved, Vet Approved
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Fluvastatin.Approved
DiethylstilbestrolThe excretion of Fluvastatin can be decreased when combined with Diethylstilbestrol.Approved, Investigational
DigoxinThe excretion of Fluvastatin can be decreased when combined with Digoxin.Approved
DiltiazemThe metabolism of Fluvastatin can be decreased when combined with Diltiazem.Approved, Investigational
DiphenadioneThe serum concentration of Diphenadione can be increased when it is combined with Fluvastatin.Experimental
DipyridamoleThe excretion of Fluvastatin can be decreased when combined with Dipyridamole.Approved
DocetaxelThe risk or severity of myopathy and rhabdomyolysis can be increased when Docetaxel is combined with Fluvastatin.Approved, Investigational
DovitinibThe excretion of Fluvastatin can be decreased when combined with Dovitinib.Investigational
DoxycyclineThe metabolism of Fluvastatin can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
ElacridarThe excretion of Fluvastatin can be decreased when combined with Elacridar.Investigational
EltrombopagThe serum concentration of Fluvastatin can be increased when it is combined with Eltrombopag.Approved
EmetineThe risk or severity of myopathy and rhabdomyolysis can be increased when Emetine is combined with Fluvastatin.Experimental
EnalaprilThe risk or severity of myopathy and rhabdomyolysis can be increased when Enalapril is combined with Fluvastatin.Approved, Vet Approved
EnasidenibThe excretion of Fluvastatin can be decreased when combined with Enasidenib.Approved, Investigational
EnzalutamideThe serum concentration of Fluvastatin can be decreased when it is combined with Enzalutamide.Approved
EprosartanThe risk or severity of myopathy and rhabdomyolysis can be increased when Eprosartan is combined with Fluvastatin.Approved
ErlotinibThe metabolism of Fluvastatin can be decreased when combined with Erlotinib.Approved, Investigational
ErythromycinThe metabolism of Fluvastatin can be decreased when combined with Erythromycin.Approved, Investigational, Vet Approved
EstradiolThe excretion of Fluvastatin can be decreased when combined with Estradiol.Approved, Investigational, Vet Approved
Estradiol acetateThe excretion of Fluvastatin can be decreased when combined with Estradiol acetate.Approved, Investigational, Vet Approved
Estradiol benzoateThe excretion of Fluvastatin can be decreased when combined with Estradiol benzoate.Approved, Investigational, Vet Approved
Estradiol cypionateThe excretion of Fluvastatin can be decreased when combined with Estradiol cypionate.Approved, Investigational, Vet Approved
Estradiol dienanthateThe excretion of Fluvastatin can be decreased when combined with Estradiol dienanthate.Approved, Investigational, Vet Approved
Estradiol valerateThe excretion of Fluvastatin can be decreased when combined with Estradiol valerate.Approved, Investigational, Vet Approved
EstroneThe excretion of Fluvastatin can be decreased when combined with Estrone.Approved
EthanolThe risk or severity of myopathy and rhabdomyolysis can be increased when Ethanol is combined with Fluvastatin.Approved
Ethinyl EstradiolThe serum concentration of Fluvastatin can be decreased when it is combined with Ethinyl Estradiol.Approved
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Fluvastatin.Withdrawn
EtofibrateThe risk or severity of myopathy and rhabdomyolysis can be increased when Etofibrate is combined with Fluvastatin.Approved
EtravirineThe serum concentration of Fluvastatin can be increased when it is combined with Etravirine.Approved
EverolimusThe excretion of Fluvastatin can be decreased when combined with Everolimus.Approved
FelbamateThe metabolism of Fluvastatin can be decreased when combined with Felbamate.Approved
FenofibrateThe risk or severity of myopathy and rhabdomyolysis can be increased when Fenofibrate is combined with Fluvastatin.Approved
Fenofibric acidThe risk or severity of myopathy and rhabdomyolysis can be increased when Fenofibric acid is combined with Fluvastatin.Approved
FloxuridineThe metabolism of Fluvastatin can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Fluvastatin can be decreased when combined with Fluconazole.Approved, Investigational
FluindioneThe serum concentration of Fluindione can be increased when it is combined with Fluvastatin.Approved, Investigational
FluorouracilThe metabolism of Fluvastatin can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Fluvastatin can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluticasoneThe excretion of Fluvastatin can be decreased when combined with Fluticasone.Approved, Experimental, Investigational
Fluticasone furoateThe excretion of Fluvastatin can be decreased when combined with Fluticasone furoate.Approved
Fluticasone propionateThe excretion of Fluvastatin can be decreased when combined with Fluticasone propionate.Approved
FluvoxamineThe metabolism of Fluvastatin can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Fluvastatin can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Fluvastatin can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Fluvastatin can be decreased when it is combined with Fosphenytoin.Approved, Investigational
Fusidic AcidThe serum concentration of Fluvastatin can be increased when it is combined with Fusidic Acid.Approved, Investigational
GanciclovirThe risk or severity of myopathy and rhabdomyolysis can be increased when Ganciclovir is combined with Fluvastatin.Approved, Investigational
GemfibrozilThe risk or severity of rhabdomyolysis, myoglobinuria, and elevated creatine kinase (CPK) can be increased when Gemfibrozil is combined with Fluvastatin.Approved
GenisteinThe excretion of Fluvastatin can be decreased when combined with Genistein.Investigational
GlecaprevirThe excretion of Fluvastatin can be decreased when combined with Glecaprevir.Approved, Investigational
HyperforinThe excretion of Fluvastatin can be decreased when combined with Hyperforin.Nutraceutical
IbandronateThe risk or severity of myopathy and rhabdomyolysis can be increased when Ibandronate is combined with Fluvastatin.Approved, Investigational
IdelalisibThe metabolism of Fluvastatin can be decreased when combined with Idelalisib.Approved
IloprostThe risk or severity of myopathy and rhabdomyolysis can be increased when Iloprost is combined with Fluvastatin.Approved, Investigational
ImatinibThe metabolism of Fluvastatin can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Fluvastatin can be decreased when combined with Indinavir.Approved
IndomethacinThe excretion of Fluvastatin can be decreased when combined with Indomethacin.Approved, Investigational
InfliximabThe risk or severity of myopathy and rhabdomyolysis can be increased when Infliximab is combined with Fluvastatin.Approved
IpecacThe risk or severity of myopathy and rhabdomyolysis can be increased when Ipecac is combined with Fluvastatin.Approved, Withdrawn
IrinotecanThe excretion of Fluvastatin can be decreased when combined with Irinotecan.Approved, Investigational
IsavuconazoleThe serum concentration of Fluvastatin can be increased when it is combined with Isavuconazole.Approved, Investigational
IsavuconazoniumThe metabolism of Fluvastatin can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe risk or severity of myopathy and rhabdomyolysis can be increased when Isoniazid is combined with Fluvastatin.Approved, Investigational
IsotretinoinThe risk or severity of myopathy and rhabdomyolysis can be increased when Isotretinoin is combined with Fluvastatin.Approved
ItraconazoleThe metabolism of Fluvastatin can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Fluvastatin can be increased when it is combined with Ivacaftor.Approved
IvermectinThe risk or severity of myopathy and rhabdomyolysis can be increased when Ivermectin is combined with Fluvastatin.Approved, Investigational, Vet Approved
KetoconazoleThe metabolism of Fluvastatin can be decreased when combined with Ketoconazole.Approved, Investigational
L-CarnitineThe excretion of Fluvastatin can be decreased when combined with L-Carnitine.Approved, Investigational
LamivudineThe risk or severity of myopathy and rhabdomyolysis can be increased when Lamivudine is combined with Fluvastatin.Approved, Investigational
LamotrigineThe serum concentration of Fluvastatin can be decreased when it is combined with Lamotrigine.Approved, Investigational
Lanthanum carbonateThe absorption of Fluvastatin can be decreased when combined with Lanthanum carbonate.Approved
LeflunomideThe risk or severity of myopathy and rhabdomyolysis can be increased when Leflunomide is combined with Fluvastatin.Approved, Investigational
LenvatinibThe excretion of Fluvastatin can be decreased when combined with Lenvatinib.Approved, Investigational
LercanidipineThe risk or severity of myopathy and rhabdomyolysis can be increased when Lercanidipine is combined with Fluvastatin.Approved, Investigational
LetrozoleThe risk or severity of myopathy and rhabdomyolysis can be increased when Letrozole is combined with Fluvastatin.Approved, Investigational
LeuprolideThe risk or severity of myopathy and rhabdomyolysis can be increased when Leuprolide is combined with Fluvastatin.Approved, Investigational
LevothyroxineThe excretion of Fluvastatin can be decreased when combined with Levothyroxine.Approved
LobeglitazoneThe excretion of Fluvastatin can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Fluvastatin can be decreased when combined with Lopinavir.Approved
LorpiprazoleThe serum concentration of Fluvastatin can be increased when it is combined with Lorpiprazole.Approved
LovastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Fluvastatin is combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Fluvastatin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Fluvastatin can be decreased when it is combined with Lumacaftor.Approved
MebeverineThe risk or severity of myopathy and rhabdomyolysis can be increased when Mebeverine is combined with Fluvastatin.Approved, Investigational
MefloquineThe risk or severity of myopathy and rhabdomyolysis can be increased when Mefloquine is combined with Fluvastatin.Approved, Investigational
MethotrexateThe risk or severity of myopathy and rhabdomyolysis can be increased when Methotrexate is combined with Fluvastatin.Approved
MethyldopaThe risk or severity of myopathy and rhabdomyolysis can be increased when Methyldopa is combined with Fluvastatin.Approved
MetoclopramideThe risk or severity of myopathy and rhabdomyolysis can be increased when Metoclopramide is combined with Fluvastatin.Approved, Investigational
MevastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Fluvastatin is combined with Mevastatin.Experimental
MibefradilThe metabolism of Fluvastatin can be decreased when combined with Mibefradil.Investigational, Withdrawn
MiconazoleThe metabolism of Fluvastatin can be decreased when combined with Miconazole.Approved, Investigational, Vet Approved
MidostaurinThe metabolism of Fluvastatin can be decreased when combined with Midostaurin.Approved, Investigational
MinocyclineThe risk or severity of myopathy and rhabdomyolysis can be increased when Minocycline is combined with Fluvastatin.Approved, Investigational
MitotaneThe serum concentration of Fluvastatin can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Fluvastatin can be decreased when it is combined with Modafinil.Approved, Investigational
MontelukastThe risk or severity of myopathy and rhabdomyolysis can be increased when Montelukast is combined with Fluvastatin.Approved
Mycophenolate mofetilThe risk or severity of myopathy and rhabdomyolysis can be increased when Mycophenolate mofetil is combined with Fluvastatin.Approved, Investigational
NabiloneThe metabolism of Fluvastatin can be decreased when combined with Nabilone.Approved, Investigational
NafarelinThe risk or severity of myopathy and rhabdomyolysis can be increased when Nafarelin is combined with Fluvastatin.Approved
NafcillinThe serum concentration of Fluvastatin can be decreased when it is combined with Nafcillin.Approved, Investigational
NaloxoneThe metabolism of Fluvastatin can be decreased when combined with Naloxone.Approved, Vet Approved
NaltrexoneThe risk or severity of myopathy and rhabdomyolysis can be increased when Naltrexone is combined with Fluvastatin.Approved, Investigational, Vet Approved
NefazodoneThe metabolism of Fluvastatin can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Fluvastatin can be decreased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Fluvastatin can be increased when it is combined with Netupitant.Approved, Investigational
NevirapineThe metabolism of Fluvastatin can be increased when combined with Nevirapine.Approved
NiacinThe risk or severity of myopathy and rhabdomyolysis can be increased when Niacin is combined with Fluvastatin.Approved, Investigational, Nutraceutical
NicardipineThe metabolism of Fluvastatin can be decreased when combined with Nicardipine.Approved, Investigational
NifedipineThe excretion of Fluvastatin can be decreased when combined with Nifedipine.Approved
NilotinibThe metabolism of Fluvastatin can be decreased when combined with Nilotinib.Approved, Investigational
NizatidineThe risk or severity of myopathy and rhabdomyolysis can be increased when Nizatidine is combined with Fluvastatin.Approved
NorfloxacinThe risk or severity of myopathy and rhabdomyolysis can be increased when Norfloxacin is combined with Fluvastatin.Approved
NovobiocinThe excretion of Fluvastatin can be decreased when combined with Novobiocin.Approved, Investigational, Vet Approved
NystatinThe excretion of Fluvastatin can be decreased when combined with Nystatin.Approved, Vet Approved
OfloxacinThe risk or severity of myopathy and rhabdomyolysis can be increased when Ofloxacin is combined with Fluvastatin.Approved
OlaparibThe metabolism of Fluvastatin can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Fluvastatin can be increased when it is combined with Osimertinib.Approved
OuabainThe excretion of Fluvastatin can be decreased when combined with Ouabain.Approved
OxcarbazepineThe serum concentration of Fluvastatin can be decreased when it is combined with Oxcarbazepine.Approved
PaclitaxelThe risk or severity of myopathy and rhabdomyolysis can be increased when Paclitaxel is combined with Fluvastatin.Approved, Vet Approved
PalbociclibThe serum concentration of Fluvastatin can be increased when it is combined with Palbociclib.Approved, Investigational
PamidronateThe risk or severity of myopathy and rhabdomyolysis can be increased when Pamidronate is combined with Fluvastatin.Approved
PantoprazoleThe risk or severity of myopathy and rhabdomyolysis can be increased when Pantoprazole is combined with Fluvastatin.Approved
ParitaprevirThe excretion of Fluvastatin can be decreased when combined with Paritaprevir.Approved, Investigational
PazopanibFluvastatin may increase the hepatotoxic activities of Pazopanib.Approved
PenicillamineThe risk or severity of myopathy and rhabdomyolysis can be increased when Penicillamine is combined with Fluvastatin.Approved
PentobarbitalThe metabolism of Fluvastatin can be increased when combined with Pentobarbital.Approved, Investigational, Vet Approved
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Fluvastatin.Approved, Investigational
PhenobarbitalThe serum concentration of Fluvastatin can be decreased when it is combined with Phenobarbital.Approved, Investigational
PhenprocoumonThe serum concentration of Phenprocoumon can be increased when it is combined with Fluvastatin.Approved, Investigational
PibrentasvirThe excretion of Fluvastatin can be decreased when combined with Pibrentasvir.Approved, Investigational
PioglitazoneThe excretion of Fluvastatin can be decreased when combined with Pioglitazone.Approved, Investigational
PiperineThe metabolism of Fluvastatin can be decreased when combined with Piperine.Investigational
PitavastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Fluvastatin is combined with Pitavastatin.Approved
PitolisantThe serum concentration of Fluvastatin can be decreased when it is combined with Pitolisant.Approved, Investigational
PosaconazoleThe metabolism of Fluvastatin can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PosizolidThe excretion of Fluvastatin can be decreased when combined with Posizolid.Investigational
PravastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Fluvastatin is combined with Pravastatin.Approved
PrimidoneThe serum concentration of Fluvastatin can be decreased when it is combined with Primidone.Approved, Vet Approved
ProcainamideThe risk or severity of myopathy and rhabdomyolysis can be increased when Procainamide is combined with Fluvastatin.Approved
ProcarbazineThe risk or severity of myopathy and rhabdomyolysis can be increased when Procarbazine is combined with Fluvastatin.Approved, Investigational
ProgesteroneThe excretion of Fluvastatin can be decreased when combined with Progesterone.Approved, Vet Approved
PropofolThe risk or severity of myopathy and rhabdomyolysis can be increased when Propofol is combined with Fluvastatin.Approved, Investigational, Vet Approved
PropylthiouracilThe risk or severity of myopathy and rhabdomyolysis can be increased when Propylthiouracil is combined with Fluvastatin.Approved, Investigational
QuercetinThe excretion of Fluvastatin can be decreased when combined with Quercetin.Experimental, Investigational
QuinidineThe excretion of Fluvastatin can be decreased when combined with Quinidine.Approved, Investigational
QuinineThe metabolism of Fluvastatin can be increased when combined with Quinine.Approved
RanitidineThe risk or severity of myopathy and rhabdomyolysis can be increased when Ranitidine is combined with Fluvastatin.Approved
ReserpineThe excretion of Fluvastatin can be decreased when combined with Reserpine.Approved, Investigational
RifampicinThe serum concentration of Fluvastatin can be decreased when it is combined with Rifampicin.Approved
RifamycinThe metabolism of Fluvastatin can be increased when combined with Rifamycin.Investigational
RifapentineThe metabolism of Fluvastatin can be increased when combined with Rifapentine.Approved, Investigational
RifaximinThe metabolism of Fluvastatin can be increased when combined with Rifaximin.Approved, Investigational
RilpivirineThe excretion of Fluvastatin can be decreased when combined with Rilpivirine.Approved
RimexoloneThe metabolism of Fluvastatin can be increased when combined with Rimexolone.Approved
RisedronateThe risk or severity of myopathy and rhabdomyolysis can be increased when Risedronate is combined with Fluvastatin.Approved, Investigational
RisperidoneThe metabolism of Fluvastatin can be decreased when combined with Risperidone.Approved, Investigational
RitonavirThe serum concentration of Fluvastatin can be decreased when it is combined with Ritonavir.Approved, Investigational
RonifibrateThe risk or severity of myopathy and rhabdomyolysis can be increased when Ronifibrate is combined with Fluvastatin.Experimental
RosiglitazoneThe excretion of Fluvastatin can be decreased when combined with Rosiglitazone.Approved, Investigational
RosuvastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Fluvastatin is combined with Rosuvastatin.Approved
SacubitrilThe excretion of Fluvastatin can be decreased when combined with Sacubitril.Approved
SalmeterolThe risk or severity of myopathy and rhabdomyolysis can be increased when Salmeterol is combined with Fluvastatin.Approved
SaquinavirThe metabolism of Fluvastatin can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Fluvastatin can be decreased when used in combination with Sarilumab.Approved, Investigational
SecobarbitalThe metabolism of Fluvastatin can be increased when combined with Secobarbital.Approved, Vet Approved
SildenafilThe risk or severity of myopathy and rhabdomyolysis can be increased when Sildenafil is combined with Fluvastatin.Approved, Investigational
Silibinin AThe excretion of Fluvastatin can be decreased when combined with Silibinin A.Experimental, Investigational
SiltuximabThe serum concentration of Fluvastatin can be decreased when it is combined with Siltuximab.Approved, Investigational
SimeprevirThe serum concentration of Fluvastatin can be increased when it is combined with Simeprevir.Approved
SimfibrateThe risk or severity of myopathy and rhabdomyolysis can be increased when Simfibrate is combined with Fluvastatin.Experimental
SimvastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Fluvastatin is combined with Simvastatin.Approved
SirolimusThe excretion of Fluvastatin can be decreased when combined with Sirolimus.Approved, Investigational
SomatotropinThe risk or severity of myopathy and rhabdomyolysis can be increased when Somatotropin is combined with Fluvastatin.Approved, Investigational
SorafenibThe excretion of Fluvastatin can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe serum concentration of Fluvastatin can be decreased when it is combined with St. John's Wort.Approved, Investigational, Nutraceutical
StavudineThe risk or severity of myopathy and rhabdomyolysis can be increased when Stavudine is combined with Fluvastatin.Approved, Investigational
StiripentolThe serum concentration of Fluvastatin can be increased when it is combined with Stiripentol.Approved
SulfamethoxazoleThe risk or severity of myopathy and rhabdomyolysis can be increased when Sulfamethoxazole is combined with Fluvastatin.Approved
SulfasalazineThe excretion of Fluvastatin can be decreased when combined with Sulfasalazine.Approved
TacrineThe risk or severity of myopathy and rhabdomyolysis can be increased when Tacrine is combined with Fluvastatin.Investigational, Withdrawn
TacrolimusThe risk or severity of myopathy and rhabdomyolysis can be increased when Tacrolimus is combined with Fluvastatin.Approved, Investigational
Taurocholic AcidThe excretion of Fluvastatin can be decreased when combined with Taurocholic Acid.Experimental
TelaprevirThe metabolism of Fluvastatin can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe serum concentration of Fluvastatin can be increased when it is combined with Telithromycin.Approved
TerbinafineThe risk or severity of myopathy and rhabdomyolysis can be increased when Terbinafine is combined with Fluvastatin.Approved, Investigational, Vet Approved
TeriflunomideThe serum concentration of Fluvastatin can be increased when it is combined with Teriflunomide.Approved
Testosterone propionateThe serum concentration of Fluvastatin can be decreased when it is combined with Testosterone propionate.Approved, Investigational, Vet Approved, Withdrawn
TianeptineThe risk or severity of myopathy and rhabdomyolysis can be increased when Tianeptine is combined with Fluvastatin.Approved, Investigational
TioclomarolThe serum concentration of Tioclomarol can be increased when it is combined with Fluvastatin.Experimental
TipranavirThe serum concentration of Fluvastatin can be decreased when it is combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Fluvastatin can be decreased when it is combined with Tocilizumab.Approved
TrabectedinThe risk or severity of myopathy and rhabdomyolysis can be increased when Fluvastatin is combined with Trabectedin.Approved, Investigational
TriamcinoloneThe risk or severity of myopathy and rhabdomyolysis can be increased when Triamcinolone is combined with Fluvastatin.Approved, Vet Approved
TriazolamThe risk or severity of myopathy and rhabdomyolysis can be increased when Triazolam is combined with Fluvastatin.Approved, Investigational
TrimethoprimThe risk or severity of myopathy and rhabdomyolysis can be increased when Trimethoprim is combined with Fluvastatin.Approved, Vet Approved
TroglitazoneThe excretion of Fluvastatin can be decreased when combined with Troglitazone.Investigational, Withdrawn
TroleandomycinThe metabolism of Fluvastatin can be decreased when combined with Troleandomycin.Approved
UbidecarenoneThe risk or severity of myopathy and rhabdomyolysis can be decreased when Ubidecarenone is combined with Fluvastatin.Approved, Investigational, Nutraceutical
Valproic AcidThe metabolism of Fluvastatin can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe excretion of Fluvastatin can be decreased when combined with Valsartan.Approved, Investigational
ValspodarThe excretion of Fluvastatin can be decreased when combined with Valspodar.Investigational
VelpatasvirThe excretion of Fluvastatin can be decreased when combined with Velpatasvir.Approved, Investigational
VemurafenibThe serum concentration of Fluvastatin can be decreased when it is combined with Vemurafenib.Approved
VerapamilThe metabolism of Fluvastatin can be decreased when combined with Verapamil.Approved
VinblastineThe excretion of Fluvastatin can be decreased when combined with Vinblastine.Approved
VincristineThe risk or severity of myopathy and rhabdomyolysis can be increased when Vincristine is combined with Fluvastatin.Approved, Investigational
VoriconazoleThe serum concentration of Fluvastatin can be increased when it is combined with Voriconazole.Approved, Investigational
VoxilaprevirThe excretion of Fluvastatin can be decreased when combined with Voxilaprevir.Approved, Investigational
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Fluvastatin.Approved
ZidovudineThe serum concentration of Fluvastatin can be decreased when it is combined with Zidovudine.Approved
ZiprasidoneThe metabolism of Fluvastatin can be decreased when combined with Ziprasidone.Approved
ZosuquidarThe excretion of Fluvastatin can be decreased when combined with Zosuquidar.Investigational
Food Interactions
  • May be taken with or without food, but should be taken consistently.
  • When given with an evening meal, Cmax and AUC decreased while Tmax increased 2-fold

References

Synthesis Reference

Gustavo Frenkel, Eyal Gilboa, "Process for the preparation of fluvastatin sodium crystal form XIV." U.S. Patent US20050119342, issued June 02, 2005.

US20050119342
General References
  1. Toda T, Eliasson E, Ask B, Inotsume N, Rane A: Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes. Basic Clin Pharmacol Toxicol. 2009 Nov;105(5):327-32. doi: 10.1111/j.1742-7843.2009.00453.x. Epub 2009 Aug 6. [PubMed:19663817]
External Links
Human Metabolome Database
HMDB0015227
KEGG Drug
D07983
KEGG Compound
C07014
PubChem Compound
1548972
PubChem Substance
46505668
ChemSpider
1265982
ChEBI
5136
ChEMBL
CHEMBL350239
Therapeutic Targets Database
DAP000554
PharmGKB
PA449688
HET
115
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fluvastatin
ATC Codes
C10AA04 — Fluvastatin
AHFS Codes
  • 24:06.08 — Hmg-coa Reductase Inhibitors
FDA label
Download (84.5 KB)
MSDS
Download (101 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers1
1RecruitingTreatmentGliomas1
2CompletedBasic ScienceAntiphospholipid Syndrome1
2CompletedTreatmentAlport Syndrome1
2CompletedTreatmentCancer, Breast1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2CompletedTreatmentProstate Cancer1
2TerminatedPreventionAging / Inflammatory Reaction1
2Unknown StatusTreatmentAortic Valve Stenosis1
2WithdrawnTreatmentHepatitis C Viral Infection / Hepatitis C Virus (HCV)1
2, 3TerminatedPreventionTransplantation, Renal1
3CompletedTreatmentAtherosclerosis / Cardiovascular Disease (CVD)1
3CompletedTreatmentChronic Nephropathy / High Blood Pressure (Hypertension) / Proteinuria1
3CompletedTreatmentDyslipidemias1
3CompletedTreatmentHeterozygous Familial Hypercholesterolemia / Mixed hypercholesterolemia1
3CompletedTreatmentHigh Blood Cholesterol Level1
3CompletedTreatmentHigh Blood Cholesterol Level / Mixed hypercholesterolemia1
3Not Yet RecruitingTreatmentHigh Blood Cholesterol Level1
3RecruitingTreatmentHigh Blood Cholesterol Level1
3TerminatedTreatmentHigh Blood Cholesterol Level1
4CompletedNot AvailableDrug-Interactions1
4CompletedPreventionGraft Vasculopathy1
4CompletedTreatmentChronic Stable Angina Pectoris / Non ST Segment Elevation Myocardial Infarction (NSTEMI) / Unstable Angina Pectoris1
4CompletedTreatmentCoronary Heart Disease (CHD) / High Blood Cholesterol Level1
4CompletedTreatmentCoronary Heart Disease (CHD) / Myocardial Infarction1
4CompletedTreatmentDyslipidemias3
4CompletedTreatmentDyslipidemias / High Blood Pressure (Hypertension)1
4CompletedTreatmentHigh Blood Cholesterol Level1
4CompletedTreatmentHypertension, Dyslypidaemia1
4CompletedTreatmentLipid Metabolism Disorders1
4CompletedTreatmentMetabolic Syndromes2
4CompletedTreatmentBone destruction1
4RecruitingBasic ScienceAdipose Tissue, Brown / Clinical Trial / Insulin Resistance1
4RecruitingPreventionHigh Blood Pressure (Hypertension) / Strokes / Transient Ischaemic Attack (TIA)1
4RecruitingTreatmentCoronary Artery Disease1
4SuspendedPreventionAortic Valve Stenosis1
4Unknown StatusPreventionHeart Transplantation / High Blood Cholesterol Level1
4Unknown StatusTreatmentAtherosclerosis / Coronary Heart Disease (CHD)1
Not AvailableCompletedNot AvailableCardiovascular Disease (CVD) / Type 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableHigh Blood Cholesterol Level1
Not AvailableCompletedPreventionAtherosclerosis1
Not AvailableCompletedTreatmentHepatitis C Viral Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Advanced Pharmaceutical Services Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Direct Dispensing Inc.
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
Dosage forms
FormRouteStrength
Tablet, film coated, extended releaseOral80 mg/1
CapsuleOral20 mg/1
CapsuleOral40 mg/1
CapsuleOral20 mg
CapsuleOral40 mg
Tablet, extended releaseOral80 mg/1
Tablet, extended releaseOral80 mg
Prices
Unit descriptionCostUnit
Lescol XL 80 mg 24 Hour tablet4.25USD tablet
Lescol xl 80 mg tablet4.24USD tablet
Lescol xl 80 mg tablet sa3.66USD tablet
Lescol 20 mg capsule3.38USD capsule
Lescol 40 mg capsule3.37USD capsule
Lescol Xl 80 mg Extended-Release Tablet1.62USD tablet
Lescol 40 mg Capsule1.35USD capsule
Lescol 20 mg Capsule0.96USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5354772No1994-10-112011-10-11Us
CA2346868No2008-09-092019-10-12Canada
CA2085037No2000-11-282012-12-10Canada
US6242003Yes2000-10-132020-10-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)194-197 °CHojjati, Mohammad; Journal of Supercritical Fluids 2007, V41(2), P187-194 CAPLUS
water solubility0.46 mg/LNot Available
logP4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00441 mg/mLALOGPS
logP3.69ALOGPS
logP3.83ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.69 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity114.86 m3·mol-1ChemAxon
Polarizability44.31 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9943
Blood Brain Barrier+0.9382
Caco-2 permeable-0.5053
P-glycoprotein substrateNon-substrate0.5176
P-glycoprotein inhibitor INon-inhibitor0.7395
P-glycoprotein inhibitor IINon-inhibitor0.8381
Renal organic cation transporterNon-inhibitor0.8823
CYP450 2C9 substrateNon-substrate0.7305
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.6111
CYP450 1A2 substrateNon-inhibitor0.6003
CYP450 2C9 inhibitorNon-inhibitor0.675
CYP450 2D6 inhibitorNon-inhibitor0.8983
CYP450 2C19 inhibitorNon-inhibitor0.6314
CYP450 3A4 inhibitorNon-inhibitor0.8811
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.809
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7909
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9472 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9899
hERG inhibition (predictor II)Non-inhibitor0.848
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrroles
Sub Class
Substituted pyrroles
Direct Parent
Phenylpyrroles
Alternative Parents
N-alkylindoles / Indoles / Medium-chain hydroxy acids and derivatives / Medium-chain fatty acids / Beta hydroxy acids and derivatives / Fluorobenzenes / Halogenated fatty acids / Heterocyclic fatty acids / Hydroxy fatty acids / Unsaturated fatty acids
show 12 more
Substituents
3-phenylpyrrole / N-alkylindole / Indole / Indole or derivatives / Medium-chain hydroxy acid / Medium-chain fatty acid / Beta-hydroxy acid / Fluorobenzene / Halobenzene / Halogenated fatty acid
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
statin (synthetic), (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (CHEBI:5136)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Nadph binding
Specific Function
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including...
Gene Name
HMGCR
Uniprot ID
P04035
Uniprot Name
3-hydroxy-3-methylglutaryl-coenzyme A reductase
Molecular Weight
97475.155 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Podar K, Tai YT, Hideshima T, Vallet S, Richardson PG, Anderson KC: Emerging therapies for multiple myeloma. Expert Opin Emerg Drugs. 2009 Mar;14(1):99-127. doi: 10.1517/14728210802676278 . [PubMed:19249983]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Fischer V, Johanson L, Heitz F, Tullman R, Graham E, Baldeck JP, Robinson WT: The 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor fluvastatin: effect on human cytochrome P-450 and implications for metabolic drug interactions. Drug Metab Dispos. 1999 Mar;27(3):410-6. [PubMed:10064574]
  2. Toda T, Eliasson E, Ask B, Inotsume N, Rane A: Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes. Basic Clin Pharmacol Toxicol. 2009 Nov;105(5):327-32. doi: 10.1111/j.1742-7843.2009.00453.x. Epub 2009 Aug 6. [PubMed:19663817]
  3. Scripture CD, Pieper JA: Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40(4):263-81. [PubMed:11368292]
  4. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Kivisto KT, Niemi M, Schaeffeler E, Pitkala K, Tilvis R, Fromm MF, Schwab M, Eichelbaum M, Strandberg T: Lipid-lowering response to statins is affected by CYP3A5 polymorphism. Pharmacogenetics. 2004 Aug;14(8):523-5. [PubMed:15284534]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Fischer V, Johanson L, Heitz F, Tullman R, Graham E, Baldeck JP, Robinson WT: The 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor fluvastatin: effect on human cytochrome P-450 and implications for metabolic drug interactions. Drug Metab Dispos. 1999 Mar;27(3):410-6. [PubMed:10064574]
  2. Toda T, Eliasson E, Ask B, Inotsume N, Rane A: Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes. Basic Clin Pharmacol Toxicol. 2009 Nov;105(5):327-32. doi: 10.1111/j.1742-7843.2009.00453.x. Epub 2009 Aug 6. [PubMed:19663817]
  3. Scripture CD, Pieper JA: Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40(4):263-81. [PubMed:11368292]
  4. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Fischer V, Johanson L, Heitz F, Tullman R, Graham E, Baldeck JP, Robinson WT: The 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor fluvastatin: effect on human cytochrome P-450 and implications for metabolic drug interactions. Drug Metab Dispos. 1999 Mar;27(3):410-6. [PubMed:10064574]
  2. Toda T, Eliasson E, Ask B, Inotsume N, Rane A: Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes. Basic Clin Pharmacol Toxicol. 2009 Nov;105(5):327-32. doi: 10.1111/j.1742-7843.2009.00453.x. Epub 2009 Aug 6. [PubMed:19663817]
  3. Scripture CD, Pieper JA: Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40(4):263-81. [PubMed:11368292]
  4. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Cohen LH, van Leeuwen RE, van Thiel GC, van Pelt JF, Yap SH: Equally potent inhibitors of cholesterol synthesis in human hepatocytes have distinguishable effects on different cytochrome P450 enzymes. Biopharm Drug Dispos. 2000 Dec;21(9):353-64. [PubMed:11523064]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Cohen LH, van Leeuwen RE, van Thiel GC, van Pelt JF, Yap SH: Equally potent inhibitors of cholesterol synthesis in human hepatocytes have distinguishable effects on different cytochrome P450 enzymes. Biopharm Drug Dispos. 2000 Dec;21(9):353-64. [PubMed:11523064]
  2. Scripture CD, Pieper JA: Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40(4):263-81. [PubMed:11368292]
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Kopplow K, Letschert K, Konig J, Walter B, Keppler D: Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells. Mol Pharmacol. 2005 Oct;68(4):1031-8. Epub 2005 Jul 26. [PubMed:16046661]
  2. Karlgren M, Ahlin G, Bergstrom CA, Svensson R, Palm J, Artursson P: In vitro and in silico strategies to identify OATP1B1 inhibitors and predict clinical drug-drug interactions. Pharm Res. 2012 Feb;29(2):411-26. doi: 10.1007/s11095-011-0564-9. Epub 2011 Aug 23. [PubMed:21861202]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Kopplow K, Letschert K, Konig J, Walter B, Keppler D: Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells. Mol Pharmacol. 2005 Oct;68(4):1031-8. Epub 2005 Jul 26. [PubMed:16046661]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Kopplow K, Letschert K, Konig J, Walter B, Keppler D: Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells. Mol Pharmacol. 2005 Oct;68(4):1031-8. Epub 2005 Jul 26. [PubMed:16046661]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Ekins S, Johnston JS, Bahadduri P, D'Souza VM, Ray A, Chang C, Swaan PW: In vitro and pharmacophore-based discovery of novel hPEPT1 inhibitors. Pharm Res. 2005 Apr;22(4):512-7. Epub 2005 Apr 7. [PubMed:15846457]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Ellis LC, Hawksworth GM, Weaver RJ: ATP-dependent transport of statins by human and rat MRP2/Mrp2. Toxicol Appl Pharmacol. 2013 Jun 1;269(2):187-94. doi: 10.1016/j.taap.2013.03.019. Epub 2013 Apr 2. [PubMed:23562342]

Drug created on June 13, 2005 07:24 / Updated on August 15, 2018 09:48