Bezafibrate

Bezafibrate Basic information
Product Name:Bezafibrate
Synonyms:Bezafibrate D6 (dimethyl D6);Bezabrate D6 (DiMethyl D6);2-(4-{2-[(4-chlorophenyl)forMaMido]ethyl}phenoxy)-2-Methylpropanoic acid;Bezafibrate-d6;BEZAFIBRATE EPB(CRM STANDARD);BEZAFIBRATE MM(CRM STANDARD);bezafibrat;bezafibrato
CAS:41859-67-0
MF:C19H20ClNO4
MW:361.82
EINECS:255-567-9
Product Categories:Intracellular receptor;Intermediates & Fine Chemicals;Active Pharmaceutical Ingredients;Pharmaceuticals;Pharmaceutical intermediates;Cardiovascular Drugs
Mol File:41859-67-0.mol
Bezafibrate Structure
Bezafibrate Chemical Properties
Melting point 184 °C
Boiling point 572.1±45.0 °C(Predicted)
density 1.260±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMF: soluble
pka3.29±0.10(Predicted)
form solid
color White to Off-White
Merck 14,1195
Stability:Hygroscopic
LogP2.504 (est)
CAS DataBase Reference41859-67-0(CAS DataBase Reference)
EPA Substance Registry SystemPropanoic acid, 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methyl- (41859-67-0)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 36
WGK Germany 1
RTECS UE8755000
HS Code 29242990
ToxicityLD50 oral in rat: 1082mg/kg
MSDS Information
Bezafibrate Usage And Synthesis
DescriptionBezafibrate is a non-selective agonist of peroxisome proliferator-activated receptors (PPARs; EC50s = 50, 60, and 20 μM for human PPARα, PPARγ, and PPARδ, respectively). It reduces triglyceride levels and the size of lipid droplets in an oleic acid-induced HepaRG hepatocyte model of steatosis when used at a concentration of 25 μM. Bezafibrate (10 mg/kg per day) reduces plasma VLDL and LDL mass and triglyceride and free fatty acid levels in a high-fructose plus lard diet-induced rat model of insulin resistance.
Chemical PropertiesOff-White Solid
OriginatorBezafibrate,Eipico Co.
UsesAntilipemic
Usesantihyperlipidemic
Usesanti-hyperlipoproteinemic
UsesBezafibrate has been used:
  • a supplement in the standard diet (SD)?for mice to study its effect on diabetes
  • to evaluate its effect on hepatitis C virus (HCV) assembly and secretion
  • to evaluate its effect on gonadal steroidogenesis and?spermatogenesis?of zebrafish and also used as standard for HPLC

DefinitionChEBI: Bezafibrate is a monocarboxylic acid amide obtained by the formal condensation of the carboxy group of 4-chlorobenzoic acid with the amino group of 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoic acid. Benafibrate is used for the treatment of hyperlipidaemia. It has a role as a xenobiotic, an environmental contaminant, a geroprotector and an antilipemic drug. It is a monocarboxylic acid, an aromatic ether, a member of monochlorobenzenes and a monocarboxylic acid amide. It is functionally related to a propionic acid.
Manufacturing Process0.292 moles p-chlorobenzoyl chloride and 50 ml dry pyridine were added dropwise to 0.146 moles tyramine in 60 ml dry pyridine for 10 minutes. Then the mixture was poured in about 500 g of ice with water. The fallen-out crystals was filtered off, washed with diluted HCl, water and NaHCO3 solution and dried. It was recrystallized from acetone to give di(4-chlorobenzoyl) tyramine; yield 98 %; MP: 203°-205°C.
0.11 moles above product in 400 ml methanol was mixed with 130 ml 2 N KOH and heated at 40°-45°C for 1 hour. On cooling 130 ml 2 N HCl was added. The fallen-out precipitate was filtered off, filtrate was distilled off to dryness. The residue was washed with water, NaHCO3 solution and recrystallized from ethanol to give N-(4-chlorobenzoyl)tyramine; yield 91%; MP: 174°-176°C.
2.14 g sodium was dissolved in 50 ml of absolute methanol and mixed with 0.93 mole N-(4-chlorobenzoyl)tyramine. Methanol was removed in vacuum to dryness. The residue was slurried in 100 ml absolute toluene and 0.137 moles 2-bromo-2-methylpropionic acid ethyl ester was added. The suspension was heated for 25 hours at 80°C. Then it was distilled in vacuum to dryness and the residue was dissolved in CH2Cl2, washed with diluted HCl, NaOH and water, and dried over CaCl2. On removing of the solvent, the crude 2-{4-[2- (4-chlorobenzoylamino)ethyl]phenoxy}-2-methylpropionic acid ethyl ester was obtained. After recrystallization from ether/ ligroin and acetone it had MP: 96°-97°C; yield 67 %.
0.1 mole above ester in 1.5 L of dioxane was slowly mixed with 200 ml 1 N KOH at ambient temperature and stood for 2 hours, then it was heated at 40°C for 1 hour. The substance was dissolved completely. On cooling the mixture was neutralized with 200 ml 1 N HCl. The solvents were removed in vacuum. The residue was washed with water and recrystallized from acetone to give 2-{4-[2-(4-chlorobenzoylamino)ethyl]phenoxy}-2-methylpropionic acid; yield 84%; MP: 186°C.


Therapeutic FunctionAntihyperlipidemic
Biochem/physiol ActionsThe peroxisome proliferator-activated receptor (PPAR) is a member of the steroid nuclear receptor superfamily. Bezafibrate is a peroxisome proliferator-activated receptor agonist for PPARα, PPARδ, and PPARγ. Lipoprotein lipase (LPL) activator.PPARgamma agonists, including Bezafibrate, have beneficial effects in the suppression of the inflammatory response during RSV infection and therefore might have clinical efficacy in the course of severe RSV-infection.
Clinical UseHyperlipidaemia
Drug interactionsPotentially hazardous interactions with other drugs
Antibacterials: increased risk of myopathy with daptomycin - try to avoid concomitant use.
Anticoagulants: enhances effect of coumarins and phenindione; dose of anticoagulant should be reduced by up to 50% and adjusted by monitoring INR.
Antidiabetics: may improve glucose tolerance and have an additive effect with insulin or sulphonylureas.
Ciclosporin: may increase nephrotoxicity and reduce ciclosporin levels.
Colchicine: possible increased risk of myopathy.
Lipid-regulating drugs: increased risk of myopathy in combination with statins and ezetimibe - avoid with ezetimibe; do not exceed 10 mg of simvastatin and 20 mg of rosuvastatin.





Metabolism50% of the administered bezafibrate dose is recovered in the urine as unchanged drug and 20% in the form of glucuronides. Elimination is rapid, with excretion almost exclusively renal. 95% of the activity of the [14C]-labelled drug is recovered in the urine and 3% in the faeces within 48 hours.
Bezafibrate Preparation Products And Raw materials
Raw materials4-Chlorobenzoyl chloride-->Tyramine-->Ethyl 2-bromoisobutyrate-->Sodium
Chlorantraniliprole BENZYL-[2-(4-METHOXY-PHENYL)-ETHYL]-AMINE Bezafibrate (R)-(+)-2-PHENOXYPROPIONIC ACID Ethanol 2-(4-ETHYLPHENOXY)PROPANOIC ACID Methyl 2-hydroxyethyl cellulose 4-ETHYLPHENOXYACETIC ACID AKOS B013930 2-methyl-2-(4-methylphenoxy)propanoic acid 2-(4-(2-AMINOETHYL)PHENOXY)ACETIC ACID HYDROCHLORIDE 2-METHYL-2-PHENOXY-PROPIONIC ACID (S)-(-)-2-PHENOXYPROPIONIC ACID Benzamide CHEMBRDG-BB 5940492 Methyltrimethoxysilane 2-(4-isopropoxyphenyl)ethanamine N-(4-chlorobenzyl)-N-propylamine

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