Bezafibrate

Base Information

• Chemical Name: Bezafibrate
• CAS No.: 41859-67-0
• Molecular Formula: C19H20ClNO4
• Molecular Weight: 361.825
• Hs Code.: 2924299090
• European Community (EC) Number: 255-567-9,941-659-2
• NSC Number: 758174
• UNII: Y9449Q51XH
• DSSTox Substance ID: DTXSID3029869
• Nikkaji Number: J16.626J
• Wikipedia: Bezafibrate
• Wikidata: Q577387
• NCI Thesaurus Code: C87449
• RXCUI: 1525
• Pharos Ligand ID: 97VM8CG9FWFW
• Metabolomics Workbench ID: 43530
• ChEMBL ID: CHEMBL264374
• Mol file: 41859-67-0.mol

Synonyms:Azufibrat;Béfizal;Befibrat;Beza Lande;Beza Puren;Beza-Lande;Beza-Puren;Bezabeta;Bezacur;Bezafibrat PB;Bezafibrate;Bezafisal;Bezalip;Bezamerck;BM 15.075;BM-15.075;BM15.075;Cedur;Difaterol;durabezur;Eulitop;Lipox;Reducterol;Regadrin B;Sklerofibrat;Solibay

Chemical Property of Bezafibrate

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 6.29E-14mmHg at 25°C
• Melting Point: 184 °C
• Refractive Index: 1.583
• Boiling Point: 572.1 °C at 760 mmHg
• PKA: 3.29±0.10(Predicted)
• Flash Point: 299.8 °C
• PSA: 75.63000
• Density: 1.26 g/cm³
• LogP: 3.94540
• Storage Temp.: Refrigerator
• Solubility.: DMF: soluble
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 361.1080858
• Heavy Atom Count: 25
• Complexity: 452

Purity/Quality:

99% ^*data from raw suppliers

Bezafibrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C(=O)O)OC1=CC=C(C=C1)CCNC(=O)C2=CC=C(C=C2)Cl
• Recent ClinicalTrials: Study of OCA in Combination With BZF Evaluating Efficacy, Safety, and Tolerability in Participants With PBC
• Recent EU Clinical Trials: Double blind, multicentric, randomized, placebo-controlled trial, evaluating the efficacy of 24-month of bezafibrate in primary sclerosing cholangitis with persistent cholestasis despite ursodeoxycholic acid therapy
• Recent NIPH Clinical Trials: bezafibrate for post operated bilirary atresia
• Description: Bezafibrate 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.
• Uses: Antilipemic antihyperlipidemic Bezafibrate has been used:a supplement in the standard diet (SD)?for mice to study its effect on diabetesto evaluate its effect on hepatitis C virus (HCV) assembly and secretionto evaluate its effect on gonadal steroidogenesis and?spermatogenesis?of zebrafish and also used as standard for HPLC
• Therapeutic Function: Antihyperlipidemic
• Clinical Use: Hyperlipidaemia
• Drug interactions: Potentially 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.

Technology Process of Bezafibrate

There total 10 articles about Bezafibrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

isopropyl 2-(4-(2-(4-chlorobenzamido)ethyl)phenoxy)-2-methylpropanoate (153758-85-1) → bezafibrate (41859-67-0)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 70 ℃;

DOI:10.1021/acs.orglett.1c03993

Reference yield: 80.0%

→ bezafibrate (41859-67-0)

Guidance literature:

Reference yield:

chloroform (67-66-3,8013-54-5) + 4-chloro-N-(4-hydroxyphenethyl)benzamide (41859-57-8) + acetone (67-64-1) → bezafibrate (41859-67-0)

Guidance literature:

With sodium hydroxide; In water; at 50 - 60 ℃; for 1.5h;

upstream raw materials:

2-Ethylhexyl alcohol

tyramine hydrochloride

4-chloro-benzoyl chloride

4-methyl-2-pentanone

Downstream raw materials:

C₂₅H₃₀ClNO₇

C₂₄H₂₄ClNO₇

C₂₅H₃₁ClN₂O₅

C₂₃H₂₆ClNO₆

Refernces

• 1、 Delcaillau, Tristan,Falk, Eric,Gürtler, Laura,Makai, Szabolcs,Morandi, Bill. "Design and Scalable Synthesis of N-Alkylhydroxylamine Reagents for the Direct Iron-Catalyzed Installation of Medicinally Relevant Amines**". . p. 21064 - 21071. Retrieved 2020/09/21.
• 2、 -. "Pharmaceutically acceprable salts of aporphine compounds of carboxyl group-containing agents and methods for preparing the same". . . Retrieved 2009/12/28.