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Identification
NameBezafibrate
Accession NumberDB01393  (DB08380)
TypeSmall Molecule
GroupsApproved
DescriptionAntilipemic agent that lowers cholesterol and triglycerides. It decreases low density lipoproteins and increases high density lipoproteins. [PubChem]
Structure
Thumb
Synonyms
2-(P-(2-(P-Chlorobenzamido)ethyl)phenoxy)-2-methylpropionic acid
Befizal
Bezafibrat
Bezafibrato
Bezafibratum
Bezalip
Bezatol sr (tn)
Cedur
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act-bezafibrate SRTablet, extended release400 mgOralActavis Group Ptc EhfNot applicableNot applicableCanada
Bezalip SRTablet, extended release400 mgOralActavis Specialty Pharmaceuticals Co1994-12-21Not applicableCanada
Bezalip Tab 200mgTablet200 mgOralHoffmann La Roche Limited1994-12-312001-07-19Canada
Jamp-bezafibrate SRTablet, extended release400 mgOralJamp Pharma Corporation2016-04-06Not applicableCanada
PMS-bezafibrateTablet200 mgOralPharmascience Inc1999-09-01Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BefizalNot Available
BezalipNot Available
Bezalip retardNot Available
BezatolNot Available
Bezatol SRNot Available
CedurNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIY9449Q51XH
CAS number41859-67-0
WeightAverage: 361.819
Monoisotopic: 361.10808584
Chemical FormulaC19H20ClNO4
InChI KeyIIBYAHWJQTYFKB-UHFFFAOYSA-N
InChI
InChI=1S/C19H20ClNO4/c1-19(2,18(23)24)25-16-9-3-13(4-10-16)11-12-21-17(22)14-5-7-15(20)8-6-14/h3-10H,11-12H2,1-2H3,(H,21,22)(H,23,24)
IUPAC Name
2-(4-{2-[(4-chlorophenyl)formamido]ethyl}phenoxy)-2-methylpropanoic acid
SMILES
CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(O)=O
Pharmacology
IndicationFor the treatment of primary hyperlipidaemia types IIa, IIb, III, IV and V (Fredrickson classification) corresponding to groups I, II and III of the European Atherosclerosis Society guidelines - when diet alone or improvements in lifestyle such as increased exercise or weight reduction do not lead to an adequate response. Also for the treatment of secondary hyperlipidaemias, e.g. severe hypertriglyceridemias, when sufficient improvement does not occur after correction of the underlying disorder (e.g. diabetes mellitus).
Structured Indications
PharmacodynamicsBezafibrate is an antilipemic agent that lowers cholesterol and triglycerides. It decreases low density lipoproteins and increases high density lipoproteins. Bezafibrate lowers elevated blood lipids (triglycerides and cholesterol). Elevated VLDL and LDL are reduced by treatment with bezafibrate, whilst HDL-levels are increased. The activity of triglyceride lipases (lipoprotein lipase and hepatic lipoproteinlipase) involved in the catabolism of triglyceride-rich lipoproteins is increased by bezafibrate. In the course of the intensified degradation of triglyceride-rich lipoproteins (chylomicrons, VLDL) precursors for the formation of HDL are formed which explains an increase in HDL. Furthermore, cholesterol biosynthesis is reduced by bezafibrate, which is accompanied by a stimulation of the LDL-receptor-mediated lipoprotein catabolism. Elevated fibrinogen appears to be an important risk-factor, alongside the lipids, smoking and hypertension, in the development of atheroma. Fibrinogen plays an important role in viscosity, and therefore blood flow, and also appears to play an important role in thrombus development and lysability. Bezafibrate exerts an effect on thrombogenic factors. A significant decrease in elevated plasma fibrinogen levels can be achieved. This may lead, amongst other things, to a reduction in both blood and plasma viscosity. Inhibition of platelet aggregation has also been observed. A reduction in blood glucose concentration due to an increase in glucose tolerance has been reported in diabetic patients. In the same patients, the concentration of fasting and postprandial free fatty acids was reduced by bezafibrate.
Mechanism of actionLike the other fibrates, bezafibrate is an agonist of PPARα; some studies suggest it may have some activity on PPARγ and PPARδ as well.
TargetKindPharmacological actionActionsOrganismUniProt ID
Peroxisome proliferator-activated receptor alphaProteinyes
agonist
HumanQ07869 details
Peroxisome proliferator-activated receptor deltaProteinyes
agonist
HumanQ03181 details
Peroxisome proliferator-activated receptor gammaProteinyes
agonist
HumanP37231 details
Related Articles
AbsorptionBezafibrate is almost completely absorbed after oral administration. The relative bioavailability of bezafibrate retard compared to the standard form is about 70%.
Volume of distributionNot Available
Protein binding94-96% of bezafibrate is bound to protein in human serum.
Metabolism

Hepatic.

Route of eliminationNot Available
Half life1-2 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe risk or severity of adverse effects can be increased when 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE is combined with Bezafibrate.Experimental
AcenocoumarolBezafibrate may increase the anticoagulant activities of Acenocoumarol.Approved
AcetohexamideBezafibrate may increase the hypoglycemic activities of Acetohexamide.Withdrawn
AcipimoxAcipimox may increase the myopathic rhabdomyolysis activities of Bezafibrate.Approved
AmiodaroneThe metabolism of Bezafibrate can be decreased when combined with Amiodarone.Approved, Investigational
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Bezafibrate.Approved
AprepitantThe serum concentration of Bezafibrate can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Bezafibrate can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Bezafibrate can be decreased when combined with Atomoxetine.Approved
AtorvastatinBezafibrate may increase the myopathic rhabdomyolysis activities of Atorvastatin.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Bezafibrate.Withdrawn
BexaroteneThe serum concentration of Bezafibrate can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Bezafibrate can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Bezafibrate can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Bezafibrate can be decreased when it is combined with Bosentan.Approved, Investigational
CarbamazepineThe metabolism of Bezafibrate can be increased when combined with Carbamazepine.Approved, Investigational
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Bezafibrate.Withdrawn
CeritinibThe serum concentration of Bezafibrate can be increased when it is combined with Ceritinib.Approved
CerivastatinBezafibrate may increase the myopathic rhabdomyolysis activities of Cerivastatin.Withdrawn
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Bezafibrate.Approved
ChlorpropamideBezafibrate may increase the hypoglycemic activities of Chlorpropamide.Approved
CholestyramineCholestyramine can cause a decrease in the absorption of Bezafibrate resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CiprofibrateThe risk or severity of adverse effects can be increased when Ciprofibrate is combined with Bezafibrate.Approved
ClarithromycinThe metabolism of Bezafibrate can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Bezafibrate can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Bezafibrate can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Bezafibrate can be decreased when combined with Cobicistat.Approved
Coenzyme Q10Bezafibrate may increase the myopathic rhabdomyolysis activities of Coenzyme Q10.Experimental
ColchicineBezafibrate may increase the myopathic rhabdomyolysis activities of Colchicine.Approved
ColesevelamColesevelam can cause a decrease in the absorption of Bezafibrate resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Bezafibrate resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ConivaptanThe serum concentration of Bezafibrate can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Bezafibrate can be decreased when combined with Crizotinib.Approved
CyclosporineCyclosporine may increase the nephrotoxic activities of Bezafibrate.Approved, Investigational, Vet Approved
CyclosporineThe metabolism of Bezafibrate can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Bezafibrate can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Bezafibrate can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Bezafibrate can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Bezafibrate can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Bezafibrate can be decreased when combined with Delavirdine.Approved
DexamethasoneThe serum concentration of Bezafibrate can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DicoumarolBezafibrate may increase the anticoagulant activities of Dicoumarol.Approved
DihydroergotamineThe metabolism of Bezafibrate can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Bezafibrate can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Bezafibrate can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Bezafibrate can be decreased when combined with Dronedarone.Approved
EfavirenzThe serum concentration of Bezafibrate can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Bezafibrate can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Bezafibrate can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Bezafibrate can be decreased when it is combined with Eslicarbazepine acetate.Approved
Ethyl biscoumacetateBezafibrate may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtravirineThe serum concentration of Bezafibrate can be decreased when it is combined with Etravirine.Approved
EzetimibeThe risk or severity of adverse effects can be increased when Bezafibrate is combined with Ezetimibe.Approved
FluconazoleThe metabolism of Bezafibrate can be decreased when combined with Fluconazole.Approved
FluindioneBezafibrate may increase the anticoagulant activities of Fluindione.Investigational
FluvastatinBezafibrate may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved
FluvoxamineThe metabolism of Bezafibrate can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Bezafibrate can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Bezafibrate can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Bezafibrate can be increased when combined with Fosphenytoin.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Bezafibrate.Approved, Vet Approved
Fusidic AcidThe serum concentration of Bezafibrate can be increased when it is combined with Fusidic Acid.Approved
GlibornurideBezafibrate may increase the hypoglycemic activities of Glibornuride.Withdrawn
GliclazideBezafibrate may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideBezafibrate may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideBezafibrate may increase the hypoglycemic activities of Glipizide.Approved
GliquidoneBezafibrate may increase the hypoglycemic activities of Gliquidone.Approved
GlisoxepideBezafibrate may increase the hypoglycemic activities of Glisoxepide.Approved
GlyburideBezafibrate may increase the hypoglycemic activities of Glyburide.Approved
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Bezafibrate.Approved
IdelalisibThe serum concentration of Bezafibrate can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Bezafibrate can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Bezafibrate can be decreased when combined with Indinavir.Approved
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Bezafibrate.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Bezafibrate.Withdrawn
IsavuconazoniumThe metabolism of Bezafibrate can be decreased when combined with Isavuconazonium.Approved, Investigational
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Bezafibrate.Approved
IsradipineThe metabolism of Bezafibrate can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Bezafibrate can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Bezafibrate can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Bezafibrate can be decreased when combined with Ketoconazole.Approved, Investigational
LopinavirThe metabolism of Bezafibrate can be decreased when combined with Lopinavir.Approved
LovastatinBezafibrate may increase the myopathic rhabdomyolysis activities of Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Bezafibrate can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Bezafibrate can be increased when combined with Lumacaftor.Approved
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Bezafibrate.Withdrawn
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Bezafibrate.Investigational
MevastatinBezafibrate may increase the myopathic rhabdomyolysis activities of Mevastatin.Experimental
MifepristoneThe serum concentration of Bezafibrate can be increased when it is combined with Mifepristone.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Bezafibrate.Approved
MitotaneThe serum concentration of Bezafibrate can be decreased when it is combined with Mitotane.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Bezafibrate.Approved
ModafinilThe serum concentration of Bezafibrate can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Bezafibrate can be decreased when it is combined with Nafcillin.Approved
NefazodoneThe metabolism of Bezafibrate can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Bezafibrate can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Bezafibrate can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Bezafibrate can be increased when combined with Nevirapine.Approved
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Bezafibrate.Withdrawn
NilotinibThe metabolism of Bezafibrate can be decreased when combined with Nilotinib.Approved, Investigational
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Bezafibrate.Withdrawn
OlaparibThe metabolism of Bezafibrate can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Bezafibrate can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Bezafibrate can be increased when it is combined with Palbociclib.Approved
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Bezafibrate.Approved
PentobarbitalThe metabolism of Bezafibrate can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Bezafibrate.Approved
PhenindioneBezafibrate may increase the anticoagulant activities of Phenindione.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Bezafibrate.Withdrawn
PhenobarbitalThe metabolism of Bezafibrate can be increased when combined with Phenobarbital.Approved
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Bezafibrate.Withdrawn
PhenprocoumonBezafibrate may increase the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe metabolism of Bezafibrate can be increased when combined with Phenytoin.Approved, Vet Approved
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Bezafibrate.Approved
PitavastatinBezafibrate may increase the myopathic rhabdomyolysis activities of Pitavastatin.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Bezafibrate.Withdrawn
PosaconazoleThe metabolism of Bezafibrate can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinBezafibrate may increase the myopathic rhabdomyolysis activities of Pravastatin.Approved
PrimidoneThe metabolism of Bezafibrate can be increased when combined with Primidone.Approved, Vet Approved
RaltegravirRaltegravir may increase the myopathic rhabdomyolysis activities of Bezafibrate.Approved
RanolazineThe metabolism of Bezafibrate can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Bezafibrate.Approved
RifabutinThe metabolism of Bezafibrate can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Bezafibrate can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Bezafibrate can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Bezafibrate can be decreased when combined with Ritonavir.Approved, Investigational
RosuvastatinBezafibrate may increase the myopathic rhabdomyolysis activities of Rosuvastatin.Approved
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Bezafibrate.Withdrawn
SaquinavirThe metabolism of Bezafibrate can be decreased when combined with Saquinavir.Approved, Investigational
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Bezafibrate.Approved, Investigational, Vet Approved
SildenafilThe metabolism of Bezafibrate can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Bezafibrate can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Bezafibrate can be increased when it is combined with Simeprevir.Approved
SimvastatinBezafibrate may increase the myopathic rhabdomyolysis activities of Simvastatin.Approved
St. John's WortThe serum concentration of Bezafibrate can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Bezafibrate can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Bezafibrate can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulpirideThe risk or severity of adverse effects can be increased when Bezafibrate is combined with Sulpiride.Approved
TelaprevirThe metabolism of Bezafibrate can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Bezafibrate can be decreased when combined with Telithromycin.Approved
TiclopidineThe metabolism of Bezafibrate can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Bezafibrate can be decreased when it is combined with Tocilizumab.Approved
TolazamideBezafibrate may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideBezafibrate may increase the hypoglycemic activities of Tolbutamide.Approved
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Bezafibrate.Approved
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Bezafibrate.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Bezafibrate.Approved
Ursodeoxycholic acidThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Bezafibrate.Approved, Investigational
VenlafaxineThe metabolism of Bezafibrate can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Bezafibrate can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Bezafibrate can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinBezafibrate may increase the anticoagulant activities of Warfarin.Approved
ZiprasidoneThe metabolism of Bezafibrate can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Authors unspecified: Secondary prevention by raising HDL cholesterol and reducing triglycerides in patients with coronary artery disease. Circulation. 2000 Jul 4;102(1):21-7. [PubMed:10880410 ]
  2. Tenenbaum A, Motro M, Fisman EZ, Tanne D, Boyko V, Behar S: Bezafibrate for the secondary prevention of myocardial infarction in patients with metabolic syndrome. Arch Intern Med. 2005 May 23;165(10):1154-60. [PubMed:15911729 ]
  3. Tenenbaum A, Motro M, Fisman EZ, Schwammenthal E, Adler Y, Goldenberg I, Leor J, Boyko V, Mandelzweig L, Behar S: Peroxisome proliferator-activated receptor ligand bezafibrate for prevention of type 2 diabetes mellitus in patients with coronary artery disease. Circulation. 2004 May 11;109(18):2197-202. Epub 2004 May 3. [PubMed:15123532 ]
  4. Tenenbaum A, Fisman EZ, Boyko V, Benderly M, Tanne D, Haim M, Matas Z, Motro M, Behar S: Attenuation of progression of insulin resistance in patients with coronary artery disease by bezafibrate. Arch Intern Med. 2006 Apr 10;166(7):737-41. [PubMed:16606809 ]
External Links
ATC CodesC10AB02
AHFS Codes
  • 24:06.06
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9246
Blood Brain Barrier+0.8773
Caco-2 permeable-0.5564
P-glycoprotein substrateSubstrate0.6325
P-glycoprotein inhibitor INon-inhibitor0.8387
P-glycoprotein inhibitor IINon-inhibitor0.7329
Renal organic cation transporterNon-inhibitor0.8161
CYP450 2C9 substrateNon-substrate0.7725
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7261
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.883
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5096
Ames testNon AMES toxic0.7749
CarcinogenicityNon-carcinogens0.7815
BiodegradationNot ready biodegradable0.9902
Rat acute toxicity2.4927 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9928
hERG inhibition (predictor II)Non-inhibitor0.6481
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tablet, extended releaseOral400 mg
TabletOral200 mg
Prices
Unit descriptionCostUnit
Bezalip 400 mg Sustained-Release Tablet1.96USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point186 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00155 mg/mLALOGPS
logP3.97ALOGPS
logP3.99ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.83ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.63 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity95.96 m3·mol-1ChemAxon
Polarizability37.53 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentPhenoxyacetic acid derivatives
Alternative Parents
Substituents
  • Phenoxyacetate
  • 4-halobenzoic acid or derivatives
  • Phenethylamine
  • Benzoic acid or derivatives
  • Benzamide
  • Phenol ether
  • Benzoyl
  • Halobenzene
  • Chlorobenzene
  • Alkyl aryl ether
  • Aryl halide
  • Aryl chloride
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fa...
Gene Name:
PPARA
Uniprot ID:
Q07869
Molecular Weight:
52224.595 Da
References
  1. Pedraza N, Solanes G, Carmona MC, Iglesias R, Vinas O, Mampel T, Vazquez M, Giralt M, Villarroya F: Impaired expression of the uncoupling protein-3 gene in skeletal muscle during lactation: fibrates and troglitazone reverse lactation-induced downregulation of the uncoupling protein-3 gene. Diabetes. 2000 Jul;49(7):1224-30. [PubMed:10909982 ]
  2. Cabrero A, Alegret M, Sanchez R, Adzet T, Laguna JC, Vazquez M: Peroxisome proliferator-activated receptor alpha (PPARalpha) activators, bezafibrate and Wy-14,643, increase uncoupling protein-3 mRNA levels without modifying the mitochondrial membrane potential in primary culture of rat preadipocytes. Arch Biochem Biophys. 2000 Aug 15;380(2):353-9. [PubMed:10933891 ]
  3. Inoue I, Goto S, Matsunaga T, Nakajima T, Awata T, Hokari S, Komoda T, Katayama S: The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells. Metabolism. 2001 Jan;50(1):3-11. [PubMed:11172467 ]
  4. Guan Y, Breyer MD: Peroxisome proliferator-activated receptors (PPARs): novel therapeutic targets in renal disease. Kidney Int. 2001 Jul;60(1):14-30. [PubMed:11422732 ]
  5. Bonilla S, Redonnet A, Noel-Suberville C, Groubet R, Pallet V, Higueret P: Effect of a pharmacological activation of PPAR on the expression of RAR and TR in rat liver. J Physiol Biochem. 2001 Mar;57(1):1-8. [PubMed:11519881 ]
  6. Goldenberg I, Benderly M, Goldbourt U: Update on the use of fibrates: focus on bezafibrate. Vasc Health Risk Manag. 2008;4(1):131-41. [PubMed:18629356 ]
  7. Fruchart JC, Duriez P: Mode of action of fibrates in the regulation of triglyceride and HDL-cholesterol metabolism. Drugs Today (Barc). 2006 Jan;42(1):39-64. [PubMed:16511610 ]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as ...
Gene Name:
PPARD
Uniprot ID:
Q03181
Molecular Weight:
49902.99 Da
References
  1. Tenenbaum A, Motro M, Fisman EZ: Dual and pan-peroxisome proliferator-activated receptors (PPAR) co-agonism: the bezafibrate lessons. Cardiovasc Diabetol. 2005 Sep 16;4:14. [PubMed:16168052 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation...
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
References
  1. Tenenbaum A, Motro M, Fisman EZ: Dual and pan-peroxisome proliferator-activated receptors (PPAR) co-agonism: the bezafibrate lessons. Cardiovasc Diabetol. 2005 Sep 16;4:14. [PubMed:16168052 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
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. 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:
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. 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:
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. 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 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
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, 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. Sharma P, Holmes VE, Elsby R, Lambert C, Surry D: Validation of cell-based OATP1B1 assays to assess drug transport and the potential for drug-drug interaction to support regulatory submissions. Xenobiotica. 2010 Jan;40(1):24-37. doi: 10.3109/00498250903351013. [PubMed:19919292 ]
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Drug created on July 08, 2007 11:01 / Updated on August 17, 2016 12:23