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Identification
NameFluvastatin
Accession NumberDB01095  (APRD00346)
TypeSmall Molecule
GroupsApproved
DescriptionFluvastatin 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.
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fluvastatin Sodium ERTablet, extended release80 mg/1OralSandoz Inc2015-10-16Not applicableUs
LescolCapsule20 mg/1OralNovartis Pharmaceuticals Corporation1993-12-30Not applicableUs
LescolCapsule20 mg/1OralPhysicians Total Care, Inc.1994-06-10Not applicableUs
LescolCapsule40 mg/1OralNovartis Pharmaceuticals Corporation1993-12-30Not applicableUs
LescolCapsule40 mg/1OralPhysicians Total Care, Inc.2002-03-08Not applicableUs
Lescol 20mgCapsule20 mgOralNovartis Pharmaceuticals Canada Inc1994-12-31Not applicableCanada
Lescol 40mgCapsule40 mgOralNovartis Pharmaceuticals Canada Inc1994-12-31Not applicableCanada
Lescol XLTablet, extended release80 mg/1OralCarilion Materials Management2000-10-06Not applicableUs
Lescol XLTablet, extended release80 mg/1OralNovartis Pharmaceuticals Corporation2000-10-06Not applicableUs
Lescol XLTablet, extended release80 mg/1OralPhysicians Total Care, Inc.2002-03-12Not applicableUs
Lescol XLTablet, extended release80 mgOralNovartis Pharmaceuticals Canada Inc2004-04-05Not applicableCanada
Sandoz FluvastatinCapsule20 mgOralSandoz Canada Incorporated2013-02-15Not applicableCanada
Sandoz FluvastatinCapsule40 mgOralSandoz Canada Incorporated2013-02-15Not applicableCanada
Teva-fluvastatinCapsule20 mgOralTeva Canada Limited2012-12-11Not applicableCanada
Teva-fluvastatinCapsule40 mgOralTeva Canada Limited2012-12-11Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FluvastatinCapsule20 mg/1OralTeva Pharmaceuticals USA Inc2012-07-05Not applicableUs
FluvastatinCapsule40 mg/1OralTeva Pharmaceuticals USA Inc2012-07-05Not applicableUs
Fluvastatin SodiumTablet, film coated, extended release80 mg/1OralTeva Pharmaceuticals Usa, Inc.2016-06-02Not applicableUs
Fluvastatin SodiumCapsule40 mg/1OralMylan Pharmaceuticals Inc.2013-03-19Not applicableUs
Fluvastatin SodiumCapsule20 mg/1OralCarilion Materials Management2013-03-19Not applicableUs
Fluvastatin SodiumTablet, film coated, extended release80 mg/1OralMylan Pharmaceuticals Inc.2015-09-11Not applicableUs
Fluvastatin SodiumCapsule40 mg/1OralCarilion Materials Management2013-03-19Not applicableUs
Fluvastatin SodiumCapsule20 mg/1OralMylan Pharmaceuticals Inc.2013-03-19Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CanefAstraZeneca
CranocAstellas
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Fluvastatin Sodium
Thumb
  • InChI Key: ZGGHKIMDNBDHJB-UHFFFAOYNA-M
  • Monoisotopic Mass: 433.166531173
  • Average Mass: 433.4478
DBSALT000088
Categories
UNII4L066368AS
CAS number93957-54-1
WeightAverage: 411.4659
Monoisotopic: 411.18458653
Chemical FormulaC24H26FNO4
InChI KeyFJLGEFLZQAZZCD-NDDZYTDBNA-N
InChI
InChI=1/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-/s2
IUPAC Name
(3R,5S,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=CC=C12)C1=CC=C(F)C=C1
Pharmacology
IndicationTo 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.
Structured Indications
PharmacodynamicsFluvastatin, 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 actionFluvastatin 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
3-hydroxy-3-methylglutaryl-coenzyme A reductaseProteinyes
inhibitor
HumanP04035 details
Related Articles
AbsorptionRapidly 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 binding98% 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.

SubstrateEnzymesProduct
Fluvastatin
6-HydroxyfluvastatinDetails
Fluvastatin
N-Deisopropyl-fluvastatinDetails
Fluvastatin
5-HydroxyfluvastatinDetails
Route of eliminationWhen 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 life3 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]
ToxicityGenerally 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
PathwayCategorySMPDB ID
Fluvastatin Action PathwayDrug actionSMP00119
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Fluvastatin can be increased when it is combined with Abiraterone.Approved
AceclofenacThe metabolism of Aceclofenac can be decreased when combined with Fluvastatin.Approved
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Fluvastatin.Approved
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Fluvastatin.Approved
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Fluvastatin.Approved, Vet Approved
AcipimoxAcipimox may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved
AlosetronThe metabolism of Alosetron can be decreased when combined with Fluvastatin.Approved, Withdrawn
AlprazolamThe metabolism of Alprazolam can be decreased when combined with Fluvastatin.Approved, Illicit, Investigational
Aluminum hydroxideThe serum concentration of Fluvastatin can be decreased when it is combined with Aluminum hydroxide.Approved
Aluminum phosphateThe serum concentration of Fluvastatin can be decreased when it is combined with Aluminum phosphate.Approved
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Fluvastatin.Approved, Withdrawn
AmiodaroneThe metabolism of Fluvastatin can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Fluvastatin.Approved
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Fluvastatin.Approved
AmprenavirThe metabolism of Amprenavir can be decreased when combined with Fluvastatin.Approved
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Fluvastatin.Approved
ApixabanThe metabolism of Apixaban can be decreased when combined with Fluvastatin.Approved
AprepitantThe serum concentration of Fluvastatin can be increased when it is combined with Aprepitant.Approved, Investigational
Arachidonic AcidThe metabolism of Arachidonic Acid can be decreased when combined with Fluvastatin.Experimental
ArformoterolThe metabolism of Arformoterol can be decreased when combined with Fluvastatin.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Fluvastatin.Approved, Investigational
ArtemetherThe metabolism of Fluvastatin can be decreased when combined with Artemether.Approved
AtazanavirThe serum concentration of Fluvastatin can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Fluvastatin can be decreased when combined with Atomoxetine.Approved
AzelastineThe metabolism of Azelastine can be decreased when combined with Fluvastatin.Approved
BetaxololThe metabolism of Fluvastatin can be decreased when combined with Betaxolol.Approved
BexaroteneThe serum concentration of Fluvastatin can be decreased when it is combined with Bexarotene.Approved, Investigational
BezafibrateBezafibrate may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved
Bismuth SubcitrateThe serum concentration of Fluvastatin can be decreased when it is combined with Bismuth Subcitrate.Approved
BoceprevirThe serum concentration of Fluvastatin can be increased when it is combined with Boceprevir.Approved
BortezomibThe metabolism of Fluvastatin can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe metabolism of Fluvastatin can be increased when combined with Bosentan.Approved, Investigational
BrompheniramineThe metabolism of Brompheniramine can be decreased when combined with Fluvastatin.Approved
BuprenorphineThe metabolism of Buprenorphine can be decreased when combined with Fluvastatin.Approved, Illicit, Investigational, Vet Approved
BupropionThe metabolism of Fluvastatin can be decreased when combined with Bupropion.Approved
CabozantinibThe metabolism of Cabozantinib can be decreased when combined with Fluvastatin.Approved
CaffeineThe metabolism of Caffeine can be decreased when combined with Fluvastatin.Approved
Calcium carbonateThe serum concentration of Fluvastatin can be decreased when it is combined with Calcium carbonate.Approved
CandesartanThe metabolism of Candesartan can be decreased when combined with Fluvastatin.Approved
CapecitabineThe metabolism of Fluvastatin can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Fluvastatin can be increased when combined with Carbamazepine.Approved, Investigational
CarbinoxamineThe metabolism of Carbinoxamine can be decreased when combined with Fluvastatin.Approved
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Fluvastatin.Approved, Investigational
CelecoxibThe metabolism of Fluvastatin can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Fluvastatin can be increased when it is combined with Ceritinib.Approved
ChloroquineThe metabolism of Fluvastatin can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Fluvastatin can be decreased when combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe metabolism of Chlorpropamide can be decreased when combined with Fluvastatin.Approved
CholecalciferolThe metabolism of Fluvastatin can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CholestyramineThe serum concentration of Fluvastatin can be decreased when it is combined with Cholestyramine.Approved
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Fluvastatin.Approved
CimetidineThe metabolism of Fluvastatin can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Fluvastatin can be decreased when combined with Cinacalcet.Approved
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Fluvastatin.Approved
CiprofibrateThe risk or severity of adverse effects can be increased when Ciprofibrate is combined with Fluvastatin.Approved
CisaprideThe metabolism of Cisapride can be decreased when combined with Fluvastatin.Approved, Investigational, Withdrawn
CitalopramThe metabolism of Fluvastatin can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Fluvastatin can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Fluvastatin can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Fluvastatin can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Fluvastatin can be decreased when combined with Clomipramine.Approved, Vet Approved
ClopidogrelThe metabolism of Fluvastatin can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Fluvastatin can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Fluvastatin can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Fluvastatin can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Fluvastatin can be decreased when combined with Cocaine.Approved, Illicit
ColchicineColchicine may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved
ConivaptanThe serum concentration of Fluvastatin can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Fluvastatin can be decreased when combined with Crizotinib.Approved
CyclophosphamideThe metabolism of Cyclophosphamide can be decreased when combined with Fluvastatin.Approved, Investigational
CyclosporineThe serum concentration of Fluvastatin can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
CyclosporineThe metabolism of Fluvastatin can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Fluvastatin can be increased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Fluvastatin can be decreased when it is combined with Dabrafenib.Approved
DaclatasvirThe serum concentration of Fluvastatin can be increased when it is combined with Daclatasvir.Approved
DanazolThe serum concentration of Fluvastatin can be increased when it is combined with Danazol.Approved
DapagliflozinThe metabolism of Dapagliflozin can be decreased when combined with Fluvastatin.Approved
DapsoneThe metabolism of Dapsone can be decreased when combined with Fluvastatin.Approved, Investigational
DaptomycinThe risk or severity of adverse effects can be increased when Fluvastatin is combined with Daptomycin.Approved, Investigational
DarifenacinThe metabolism of Fluvastatin can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Fluvastatin can be increased when it is combined with Darunavir.Approved
DasabuvirThe serum concentration of Fluvastatin can be increased when it is combined with Dasabuvir.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
DesipramineThe metabolism of Fluvastatin can be decreased when combined with Desipramine.Approved
DexamethasoneThe serum concentration of Fluvastatin can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe metabolism of Dextromethorphan can be decreased when combined with Fluvastatin.Approved
DiazepamThe metabolism of Diazepam can be decreased when combined with Fluvastatin.Approved, Illicit, Vet Approved
DiclofenacThe metabolism of Diclofenac can be decreased when combined with Fluvastatin.Approved, Vet Approved
DicoumarolThe metabolism of Dicoumarol can be decreased when combined with Fluvastatin.Approved
DihydroergotamineThe metabolism of Fluvastatin can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Fluvastatin can be decreased when combined with Diltiazem.Approved
DiphenhydramineThe metabolism of Fluvastatin can be decreased when combined with Diphenhydramine.Approved
DolasetronThe metabolism of Dolasetron can be decreased when combined with Fluvastatin.Approved
DonepezilThe metabolism of Donepezil can be decreased when combined with Fluvastatin.Approved
DopamineThe metabolism of Dopamine can be decreased when combined with Fluvastatin.Approved
DorzolamideThe metabolism of Dorzolamide can be decreased when combined with Fluvastatin.Approved
DoxepinThe metabolism of Doxepin can be decreased when combined with Fluvastatin.Approved
DoxycyclineThe metabolism of Fluvastatin can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Fluvastatin.Approved, Illicit
DronedaroneThe metabolism of Fluvastatin can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Fluvastatin can be decreased when combined with Duloxetine.Approved
EfavirenzThe serum concentration of Fluvastatin can be decreased when it is combined with Efavirenz.Approved, Investigational
EletriptanThe metabolism of Eletriptan can be decreased when combined with Fluvastatin.Approved, Investigational
EliglustatThe metabolism of Fluvastatin can be decreased when combined with Eliglustat.Approved
EnzalutamideThe serum concentration of Fluvastatin can be decreased when it is combined with Enzalutamide.Approved
EpoprostenolThe metabolism of Epoprostenol can be decreased when combined with Fluvastatin.Approved
ErythromycinThe metabolism of Fluvastatin can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Fluvastatin can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstradiolThe metabolism of Estradiol can be decreased when combined with Fluvastatin.Approved, Investigational, Vet Approved
EstroneThe metabolism of Estrone can be decreased when combined with Fluvastatin.Approved
EszopicloneThe metabolism of Eszopiclone can be decreased when combined with Fluvastatin.Approved
Ethyl biscoumacetateFluvastatin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacThe metabolism of Etodolac can be decreased when combined with Fluvastatin.Approved, Investigational, Vet Approved
EtoricoxibThe metabolism of Etoricoxib can be decreased when combined with Fluvastatin.Approved, Investigational
EtravirineThe serum concentration of Fluvastatin can be decreased when it is combined with Etravirine.Approved
FelodipineThe metabolism of Fluvastatin can be decreased when combined with Felodipine.Approved, Investigational
FenofibrateThe risk or severity of adverse effects can be increased when Fenofibrate is combined with Fluvastatin.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Fluvastatin.Approved
FloxuridineThe metabolism of Fluvastatin can be decreased when combined with Floxuridine.Approved
FluconazoleThe serum concentration of Fluvastatin can be increased when it is combined with Fluconazole.Approved
FluindioneFluvastatin may increase the anticoagulant activities of Fluindione.Investigational
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Fluvastatin.Approved
FlunitrazepamThe metabolism of Flunitrazepam can be decreased when combined with Fluvastatin.Approved, Illicit
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
FlurbiprofenThe metabolism of Flurbiprofen can be decreased when combined with Fluvastatin.Approved, Investigational
FluvoxamineThe metabolism of Fluvastatin can be decreased when combined with Fluvoxamine.Approved, Investigational
FormoterolThe metabolism of Formoterol can be decreased when combined with Fluvastatin.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
Fusidic AcidThe serum concentration of Fluvastatin can be increased when it is combined with Fusidic Acid.Approved
GavestinelThe metabolism of Gavestinel can be decreased when combined with Fluvastatin.Investigational
GemfibrozilGemfibrozil may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved
GliclazideThe metabolism of Gliclazide can be decreased when combined with Fluvastatin.Approved
GlimepirideThe metabolism of Glimepiride can be decreased when combined with Fluvastatin.Approved
GlipizideThe metabolism of Glipizide can be decreased when combined with Fluvastatin.Approved
GlyburideThe metabolism of Glyburide can be decreased when combined with Fluvastatin.Approved
GuanfacineThe metabolism of Guanfacine can be decreased when combined with Fluvastatin.Approved, Investigational
HaloperidolThe metabolism of Fluvastatin can be decreased when combined with Haloperidol.Approved
HalothaneThe metabolism of Halothane can be decreased when combined with Fluvastatin.Approved, Vet Approved
HexobarbitalThe metabolism of Hexobarbital can be decreased when combined with Fluvastatin.Approved
Histamine PhosphateThe metabolism of Histamine Phosphate can be decreased when combined with Fluvastatin.Approved
HydromorphoneThe metabolism of Hydromorphone can be decreased when combined with Fluvastatin.Approved, Illicit
IbuprofenThe metabolism of Ibuprofen can be decreased when combined with Fluvastatin.Approved
IdarubicinThe metabolism of Idarubicin can be decreased when combined with Fluvastatin.Approved
IdelalisibThe serum concentration of Fluvastatin can be increased when it is combined with Idelalisib.Approved
IfosfamideThe metabolism of Ifosfamide can be decreased when combined with Fluvastatin.Approved
ImatinibThe metabolism of Fluvastatin can be decreased when combined with Imatinib.Approved
ImipramineThe metabolism of Fluvastatin can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Fluvastatin can be decreased when combined with Indinavir.Approved
indisulamThe metabolism of indisulam can be decreased when combined with Fluvastatin.Investigational
IndomethacinThe metabolism of Indomethacin can be decreased when combined with Fluvastatin.Approved, Investigational
IrbesartanThe metabolism of Fluvastatin can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Fluvastatin can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Fluvastatin can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Fluvastatin can be decreased when combined with Isradipine.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
IxazomibThe metabolism of Ixazomib can be decreased when combined with Fluvastatin.Approved
KetamineThe metabolism of Ketamine can be decreased when combined with Fluvastatin.Approved, Vet Approved
KetobemidoneThe metabolism of Ketobemidone can be decreased when combined with Fluvastatin.Approved
KetoconazoleThe metabolism of Fluvastatin can be decreased when combined with Ketoconazole.Approved, Investigational
KetoprofenThe metabolism of Ketoprofen can be decreased when combined with Fluvastatin.Approved, Vet Approved
LansoprazoleThe metabolism of Lansoprazole can be decreased when combined with Fluvastatin.Approved, Investigational
Lanthanum carbonateThe serum concentration of Lanthanum carbonate can be decreased when it is combined with Fluvastatin.Approved
LapatinibThe metabolism of Fluvastatin can be decreased when combined with Lapatinib.Approved, Investigational
LeflunomideThe metabolism of Leflunomide can be decreased when combined with Fluvastatin.Approved, Investigational
LesinuradThe metabolism of Lesinurad can be decreased when combined with Fluvastatin.Approved
LicofeloneThe metabolism of Licofelone can be decreased when combined with Fluvastatin.Investigational
LidocaineThe metabolism of Lidocaine can be decreased when combined with Fluvastatin.Approved, Vet Approved
LopinavirThe metabolism of Fluvastatin can be decreased when combined with Lopinavir.Approved
LoratadineThe metabolism of Loratadine can be decreased when combined with Fluvastatin.Approved
LorcaserinThe metabolism of Fluvastatin can be decreased when combined with Lorcaserin.Approved
LornoxicamThe metabolism of Lornoxicam can be decreased when combined with Fluvastatin.Approved
LosartanThe metabolism of Fluvastatin can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Fluvastatin can be decreased when 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 increased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Fluvastatin can be decreased when combined with Lumefantrine.Approved
LumiracoxibThe metabolism of Lumiracoxib can be decreased when combined with Fluvastatin.Approved, Investigational
MagaldrateThe serum concentration of Fluvastatin can be decreased when it is combined with Magaldrate.Withdrawn
Magnesium carbonateThe serum concentration of Fluvastatin can be decreased when it is combined with Magnesium carbonate.Approved
Magnesium hydroxideThe serum concentration of Fluvastatin can be decreased when it is combined with Magnesium hydroxide.Approved
Magnesium oxideThe serum concentration of Fluvastatin can be decreased when it is combined with Magnesium oxide.Approved
Magnesium TrisilicateThe serum concentration of Fluvastatin can be decreased when it is combined with Magnesium Trisilicate.Approved
Mefenamic acidThe metabolism of Mefenamic acid can be decreased when combined with Fluvastatin.Approved
MelatoninThe metabolism of Melatonin can be decreased when combined with Fluvastatin.Approved, Nutraceutical, Vet Approved
MeloxicamThe metabolism of Meloxicam can be decreased when combined with Fluvastatin.Approved, Vet Approved
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Fluvastatin.Investigational, Withdrawn
MestranolThe metabolism of Mestranol can be decreased when combined with Fluvastatin.Approved
MethadoneThe metabolism of Fluvastatin can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Fluvastatin can be decreased when combined with Methotrimeprazine.Approved
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Fluvastatin.Approved, Vet Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Fluvastatin.Approved, Investigational
MetronidazoleThe metabolism of Metronidazole can be decreased when combined with Fluvastatin.Approved
MifepristoneThe serum concentration of Fluvastatin can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe metabolism of Fluvastatin can be decreased when combined with Mirabegron.Approved
MirtazapineThe metabolism of Mirtazapine can be decreased when combined with Fluvastatin.Approved
MitotaneThe serum concentration of Fluvastatin can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Moclobemide can be decreased when combined with Fluvastatin.Approved
ModafinilThe serum concentration of Fluvastatin can be decreased when it is combined with Modafinil.Approved, Investigational
MontelukastThe metabolism of Montelukast can be decreased when combined with Fluvastatin.Approved
NafcillinThe serum concentration of Fluvastatin can be decreased when it is combined with Nafcillin.Approved
NaproxenThe metabolism of Naproxen can be decreased when combined with Fluvastatin.Approved, Vet Approved
NateglinideThe metabolism of Nateglinide can be decreased when combined with Fluvastatin.Approved, Investigational
NefazodoneThe metabolism of Fluvastatin can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Fluvastatin can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Fluvastatin can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Fluvastatin can be increased when combined with Nevirapine.Approved
NiacinThe risk or severity of adverse effects can be increased when Niacin is combined with Fluvastatin.Approved, Investigational, Nutraceutical
NicardipineThe metabolism of Fluvastatin can be decreased when combined with Nicardipine.Approved
NiclosamideThe metabolism of Niclosamide can be decreased when combined with Fluvastatin.Approved, Vet Approved
NicotinamideThe risk or severity of adverse effects can be increased when Nicotinamide is combined with Fluvastatin.Approved
NicotineThe metabolism of Nicotine can be decreased when combined with Fluvastatin.Approved
NilotinibThe metabolism of Fluvastatin can be decreased when combined with Nilotinib.Approved, Investigational
NortriptylineThe metabolism of Nortriptyline can be decreased when combined with Fluvastatin.Approved
OlaparibThe metabolism of Fluvastatin can be decreased when combined with Olaparib.Approved
OlodaterolThe metabolism of Olodaterol can be decreased when combined with Fluvastatin.Approved
OmbitasvirThe serum concentration of Fluvastatin can be increased when it is combined with Ombitasvir.Approved
OmeprazoleThe metabolism of Fluvastatin can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronThe metabolism of Ondansetron can be decreased when combined with Fluvastatin.Approved
OsimertinibThe serum concentration of Fluvastatin can be increased when it is combined with Osimertinib.Approved
OspemifeneThe metabolism of Ospemifene can be decreased when combined with Fluvastatin.Approved
OxaprozinThe metabolism of Oxaprozin can be decreased when combined with Fluvastatin.Approved
PaclitaxelThe metabolism of Paclitaxel can be decreased when combined with Fluvastatin.Approved, Vet Approved
PalbociclibThe serum concentration of Fluvastatin can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Fluvastatin can be increased when it is combined with Panobinostat.Approved, Investigational
ParamethadioneThe metabolism of Paramethadione can be decreased when combined with Fluvastatin.Approved
ParecoxibThe metabolism of Parecoxib can be decreased when combined with Fluvastatin.Approved
ParitaprevirThe serum concentration of Fluvastatin can be increased when it is combined with Paritaprevir.Approved
ParoxetineThe metabolism of Fluvastatin can be decreased when combined with Paroxetine.Approved, Investigational
PazopanibFluvastatin may increase the hepatotoxic activities of Pazopanib.Approved
Peginterferon alfa-2bThe serum concentration of Fluvastatin can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Fluvastatin can be increased when combined with Pentobarbital.Approved, Vet Approved
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Fluvastatin.Approved
PhenacetinThe metabolism of Phenacetin can be decreased when combined with Fluvastatin.Withdrawn
PhenindioneFluvastatin may increase the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe metabolism of Fluvastatin can be increased when combined with Phenobarbital.Approved
PhenprocoumonThe metabolism of Phenprocoumon can be decreased when combined with Fluvastatin.Approved
PhenylbutazoneThe metabolism of Phenylbutazone can be decreased when combined with Fluvastatin.Approved, Vet Approved
PhenytoinThe serum concentration of Fluvastatin can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PioglitazoneThe metabolism of Pioglitazone can be decreased when combined with Fluvastatin.Approved, Investigational
PiroxicamThe metabolism of Piroxicam can be decreased when combined with Fluvastatin.Approved, Investigational
PitavastatinThe metabolism of Pitavastatin can be decreased when combined with Fluvastatin.Approved
PosaconazoleThe metabolism of Fluvastatin can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrasugrelThe metabolism of Prasugrel can be decreased when combined with Fluvastatin.Approved
PravastatinThe metabolism of Pravastatin can be decreased when combined with Fluvastatin.Approved
PrimidoneThe metabolism of Fluvastatin can be increased when combined with Primidone.Approved, Vet Approved
ProgesteroneThe metabolism of Progesterone can be decreased when combined with Fluvastatin.Approved, Vet Approved
ProguanilThe metabolism of Proguanil can be decreased when combined with Fluvastatin.Approved
PromazineThe metabolism of Fluvastatin can be decreased when combined with Promazine.Approved, Vet Approved
PropofolThe metabolism of Propofol can be decreased when combined with Fluvastatin.Approved, Investigational, Vet Approved
PyrimethamineThe metabolism of Fluvastatin can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuazepamThe metabolism of Quazepam can be decreased when combined with Fluvastatin.Approved, Illicit
QuinidineThe metabolism of Fluvastatin can be decreased when combined with Quinidine.Approved
QuinineThe serum concentration of Fluvastatin can be increased when it is combined with Quinine.Approved
RabeprazoleThe metabolism of Fluvastatin can be decreased when combined with Rabeprazole.Approved, Investigational
RaltegravirRaltegravir may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved
RanolazineThe metabolism of Fluvastatin can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Fluvastatin can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Fluvastatin can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Fluvastatin can be increased when combined with Rifapentine.Approved
RitonavirThe serum concentration of Fluvastatin can be increased when it is combined with Ritonavir.Approved, Investigational
RofecoxibThe metabolism of Rofecoxib can be decreased when combined with Fluvastatin.Investigational, Withdrawn
RolapitantThe metabolism of Fluvastatin can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Fluvastatin can be decreased when combined with Ropinirole.Approved, Investigational
RosiglitazoneThe metabolism of Rosiglitazone can be decreased when combined with Fluvastatin.Approved, Investigational
RosuvastatinThe metabolism of Rosuvastatin can be decreased when combined with Fluvastatin.Approved
Salicylic acidThe metabolism of Salicylic acid can be decreased when combined with Fluvastatin.Approved, Vet Approved
SaquinavirThe metabolism of Fluvastatin can be decreased when combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Fluvastatin.Approved
SecobarbitalThe metabolism of Fluvastatin can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe metabolism of Selegiline can be decreased when combined with Fluvastatin.Approved, Investigational, Vet Approved
SeratrodastThe metabolism of Seratrodast can be decreased when combined with Fluvastatin.Approved, Investigational
SertralineThe metabolism of Fluvastatin can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Fluvastatin can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Fluvastatin can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Fluvastatin can be increased when it is combined with Simeprevir.Approved
SitaxentanThe metabolism of Sitaxentan can be decreased when combined with Fluvastatin.Approved, Investigational, Withdrawn
SorafenibThe metabolism of Fluvastatin can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe metabolism of Fluvastatin can be increased when combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Fluvastatin can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Fluvastatin can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Fluvastatin can be decreased when combined with Sulfamethoxazole.Approved
SulfamoxoleThe metabolism of Sulfamoxole can be decreased when combined with Fluvastatin.Approved
SulfinpyrazoneThe metabolism of Sulfinpyrazone can be decreased when combined with Fluvastatin.Approved
SulfisoxazoleThe metabolism of Fluvastatin can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SuprofenThe metabolism of Suprofen can be decreased when combined with Fluvastatin.Approved, Withdrawn
TamoxifenThe metabolism of Tamoxifen can be decreased when combined with Fluvastatin.Approved
TapentadolThe metabolism of Tapentadol can be decreased when combined with Fluvastatin.Approved
TelaprevirThe serum concentration of Fluvastatin can be increased when it is combined with Telaprevir.Approved
TelithromycinThe metabolism of Fluvastatin can be decreased when combined with Telithromycin.Approved
TemazepamThe metabolism of Temazepam can be decreased when combined with Fluvastatin.Approved
TenoxicamThe metabolism of Tenoxicam can be decreased when combined with Fluvastatin.Approved
TerbinafineThe metabolism of Fluvastatin can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TerfenadineThe metabolism of Terfenadine can be decreased when combined with Fluvastatin.Withdrawn
TeriflunomideThe metabolism of Fluvastatin can be decreased when combined with Teriflunomide.Approved
TestosteroneThe metabolism of Testosterone can be decreased when combined with Fluvastatin.Approved, Investigational
ThalidomideThe metabolism of Thalidomide can be decreased when combined with Fluvastatin.Approved, Investigational, Withdrawn
TheophyllineThe metabolism of Theophylline can be decreased when combined with Fluvastatin.Approved
ThiamylalThe metabolism of Thiamylal can be decreased when combined with Fluvastatin.Approved, Vet Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Fluvastatin.Approved
TicagrelorThe metabolism of Fluvastatin can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Fluvastatin can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Fluvastatin can be decreased when combined with Tipranavir.Approved, Investigational
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Fluvastatin.Approved
TocilizumabThe serum concentration of Fluvastatin can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Fluvastatin can be decreased when combined with Tolbutamide.Approved
TolterodineThe metabolism of Tolterodine can be decreased when combined with Fluvastatin.Approved, Investigational
TorasemideThe metabolism of Torasemide can be decreased when combined with Fluvastatin.Approved
TrabectedinFluvastatin may increase the myopathic rhabdomyolysis activities of Trabectedin.Approved, Investigational
TranylcypromineThe metabolism of Fluvastatin can be decreased when combined with Tranylcypromine.Approved
TreprostinilThe metabolism of Treprostinil can be decreased when combined with Fluvastatin.Approved, Investigational
TretinoinThe metabolism of Tretinoin can be decreased when combined with Fluvastatin.Approved, Investigational, Nutraceutical
TrimethadioneThe metabolism of Trimethadione can be decreased when combined with Fluvastatin.Approved
TrimethoprimThe metabolism of Fluvastatin can be decreased when combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe metabolism of Trimipramine can be decreased when combined with Fluvastatin.Approved
TroglitazoneThe metabolism of Troglitazone can be decreased when combined with Fluvastatin.Withdrawn
ValdecoxibThe metabolism of Valdecoxib can be decreased when combined with Fluvastatin.Investigational, Withdrawn
Valproic AcidThe metabolism of Fluvastatin can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Fluvastatin can be decreased when combined with Valsartan.Approved, Investigational
VenlafaxineThe metabolism of Fluvastatin can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Fluvastatin can be decreased when combined with Verapamil.Approved
VicrivirocThe metabolism of Vicriviroc can be decreased when combined with Fluvastatin.Investigational
VismodegibThe metabolism of Vismodegib can be decreased when combined with Fluvastatin.Approved
VoriconazoleThe metabolism of Fluvastatin can be decreased when combined with Voriconazole.Approved, Investigational
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Fluvastatin.Approved
WarfarinThe metabolism of Warfarin can be decreased when combined with Fluvastatin.Approved
XimelagatranThe metabolism of Ximelagatran can be decreased when combined with Fluvastatin.Approved, Investigational, Withdrawn
ZafirlukastThe metabolism of Fluvastatin can be decreased when combined with Zafirlukast.Approved, Investigational
ZalcitabineThe metabolism of Zalcitabine can be decreased when combined with Fluvastatin.Approved
ZaltoprofenThe metabolism of Zaltoprofen can be decreased when combined with Fluvastatin.Approved
ZidovudineThe metabolism of Zidovudine can be decreased when combined with Fluvastatin.Approved
ZileutonThe metabolism of Zileuton can be decreased when combined with Fluvastatin.Approved, Investigational, Withdrawn
ZiprasidoneThe metabolism of Fluvastatin can be decreased when combined with Ziprasidone.Approved
ZolpidemThe metabolism of Zolpidem can be decreased when combined with Fluvastatin.Approved
ZopicloneThe metabolism of Zopiclone can be decreased when combined with Fluvastatin.Approved
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
ATC CodesC10AA04
AHFS Codes
  • 24:06.08
PDB EntriesNot Available
FDA labelDownload (84.5 KB)
MSDSDownload (101 KB)
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tablet, film coated, extended releaseOral80 mg/1
CapsuleOral20 mg/1
CapsuleOral40 mg/1
CapsuleOral20 mg
CapsuleOral40 mg
Tablet, extended releaseOral80 mg
Tablet, extended releaseOral80 mg/1
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)
CA2085037 No2000-11-282012-12-10Canada
CA2346868 No2008-09-092019-10-12Canada
US5354772 No1994-10-112011-10-11Us
US6242003 Yes2000-10-132020-10-13Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point194-197 °CNot Available
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
Polarizability43.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentPhenylpyrroles
Alternative Parents
Substituents
  • 3-phenylpyrrole
  • Medium-chain hydroxy acid
  • Indole or derivatives
  • Indole
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Halogenated fatty acid
  • Halobenzene
  • Fluorobenzene
  • Beta-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Secondary alcohol
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (CHEBI:38565 )

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 ubiquinone and geranylgeranyl proteins.
Gene Name:
HMGCR
Uniprot ID:
P04035
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 ]

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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
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
substrateinhibitorinducer
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
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
substrateinhibitor
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
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
substrateinhibitorinducer
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
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
substrateinhibitor
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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 IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naph...
Gene Name:
UGT1A1
Uniprot ID:
P22309
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 regulator of isoform 1.
Gene Name:
UGT1A3
Uniprot ID:
P35503
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 suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular Weight:
60694.12 Da

Transporters

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 pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
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 ]
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), methotrexate and sulfobromophthalein (BSP). Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
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
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
substrateinhibitor
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on December 07, 2016 03:54