49562-28-9 Usage
Description
Fenofibrate, also known as Tricor, is a chlorobenzophenone derivative with structural features similar to clofibrate, but with a more potent hypocholesterolemic and triglyceride-lowering effect due to its greater lipophilic character. It is a crystalline solid and is used in the treatment of various conditions related to cardiovascular diseases and lipid metabolism.
Uses
Used in Cardiovascular Disease Treatment:
Fenofibrate is used as a lipid-lowering agent for the management of cardiovascular diseases. It helps in reducing the levels of low-density lipoprotein (LDL) cholesterol and triglycerides while increasing the levels of high-density lipoprotein (HDL) cholesterol, thus improving the overall lipid profile and reducing the risk of cardiovascular events.
Used in Research Studies:
Fenofibrate is used as a research tool to study its effect on plasma lipids, liver phenotype, and gene expression. This helps in understanding the underlying mechanisms of its action and its potential role in the treatment of various metabolic disorders.
Used in Endothelium-Dependent Vasodilation Studies:
Fenofibrate is used as a pharmacological agent to study its impact on endothelium-dependent vasodilatation of the thoracic aorta. This helps in understanding the role of fenofibrate in improving vascular function and its potential benefits in the treatment of cardiovascular diseases.
Used in Non-Alcoholic Steatohepatitis (NASH) Research:
Fenofibrate is used as a treatment agent in NASH knock-in mice along with a high-fat diet (HFD) to study its effect on the development and progression of the disease. This helps in evaluating the potential therapeutic role of fenofibrate in the management of NASH and related metabolic disorders.
Originator
Lipantyl,Fournier,France,1975
Manufacturing Process
(a) Preparation of p-(4-chlorobenzoyl)-phenoxyisobutyric acid: 1 mol of 4-
hydroxy-4'-chlorobenzophenone is dissolved in anhydrous acetone and then 5
mols of powdered sodium hydroxide is added. The corresponding sodium
phenoxide precipitates. Refluxing is effected, and then, 1.5 mols of CHCl3
diluted with anhydrous acetone is added and the resulting mixture is refluxed
for 10 hours. After cooling, water is added, the acetone is evaporated, the
aqueous phase is washed with ether and acidified and the organic phase is
redissolved in ether and extracted into a solution of bicarbonate. The
bicarbonate solution is than acidified to obtain the desired acid, having a
melting point of 185°C, with a yield of 75%.(b) Preparation of fenofibrate: 1 mol of the acid obtained is converted into its
acid chloride using thionyl chloride (2.5 mols). 1 mol of the acid chloride is
then condensed with 1.05 mol of isopropyl alcohol in the presence of 0.98 mol
of pyridine in an inert solvent such as benzene.Since traces of SO2 (which has a bad smell) may be obtained from the thionyl
chloride, it is preferable to avoid this disadvantage by carrying out the
esterification directly.
Biochem/physiol Actions
Fenofibrate increases high density lipoprotein levels by reducing cholesteryl ester transfer protein expression. It is used in treating the condition of increased cholesterol levels in the blood, abnormal lipid levels in the body and also hypertriglyceridaemia. Fenofibrate is a lipid regulating drug and proliferator-activated receptor-α (PPARα) mediates its action. It decreases the plasma levels of fibrinogen and C-reactive protein. By this fenofibrate allows better flow-mediated dilatation and reduces the risk of atherosclerosis. Fenofibrate is also known to reduce uric acid levels.
Clinical Use
#N/A
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 readjusted by monitoring
INR.
Antidiabetics: may improve glucose tolerance
and have an additive effect with insulin or
sulphonylureas.
Ciclosporin: ciclosporin levels appear to be
unaffected; however, it is recommended that
concomitant therapy should be avoided because of
the possibility of elevated serum creatinine levels.
Colchicine: possible increased risk of myopathy.
Lipid-regulating drugs: increased risk of myopathy
in combination with statins and ezetimibe
(maximum 20 mg of rosuvastatin); increased risk of
cholelithiasis and gallbladder disease with ezetimibe
- avoid with ezetimibe.
Metabolism
After oral administration, fenofibrate is rapidly
hydrolysed by esterases to the active metabolite fenofibric
acid.No unchanged fenofibrate can be detected in the plasma.
Fenofibric acid is excreted mainly in the urine, mainly as
the glucuronide conjugate, but also as a reduced form of
fenofibric acid and its glucuronide; practically all the drug
is eliminated from the body within 6 days
Check Digit Verification of cas no
The CAS Registry Mumber 49562-28-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,9,5,6 and 2 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 49562-28:
(7*4)+(6*9)+(5*5)+(4*6)+(3*2)+(2*2)+(1*8)=149
149 % 10 = 9
So 49562-28-9 is a valid CAS Registry Number.
InChI:InChI=1/C20H21ClO4/c1-13(2)24-19(23)20(3,4)25-17-11-7-15(8-12-17)18(22)14-5-9-16(21)10-6-14/h5-13H,1-4H3
49562-28-9Relevant articles and documents
Feeding Carbonylation with CO2via the Synergy of Single-Site/Nanocluster Catalysts in a Photosensitizing MOF
Fu, Shanshan,Guo, Guang-Chen,Guo, Song,Lu, Tong-Bu,Yao, Shuang,Yuan, Wenjuan,Zhang, Zhi-Ming
, p. 20792 - 20801 (2021/12/14)
Solar-driven carbonylation with CO2 replacing toxic CO as a C1 source is of considerable interest; however it remains a great challenge due to the inert CO2 molecule. Herein, we integrate cobalt single-site and ultrafine CuPd nanocluster catalysts into a
Selective oxidation of alkenes to carbonyls under mild conditions
Huo, Jie,Xiong, Daokai,Xu, Jun,Yue, Xiaoguang,Zhang, Pengfei,Zhang, Yilan
supporting information, p. 5549 - 5555 (2021/08/16)
Herein, a practical and sustainable method for the synthesis of aldehydes, ketones, and carboxylic acids from an inexpensive olefinic feedstock is described. This transformation features very sustainable and mild conditions and utilizes commercially available and inexpensive tetrahydrofuran as the additive, molecular oxygen as the sole oxidant and water as the solvent. A wide range of substituted alkenes were found to be compatible, providing the corresponding carbonyl compounds in moderate-to-good yields. The control experiments demonstrated that a radical mechanism is responsible for the oxidation reaction.
Palladium-Catalyzed Amide N-C Hiyama Cross-Coupling: Synthesis of Ketones
Idris, Muhammad Aliyu,Lee, Sunwoo
supporting information, p. 9190 - 9195 (2020/11/18)
N-Acylglutarimides and arylsiloxanes reacted in the presence of Pd(OAc)2/PCy3, Et3N·3HF, and LiOAc to provide the corresponding arylketones in good yields. Aryl-, vinyl-, and alkyl-substituted N-acylglutarimides showed good activity in the coupling reactions of arylsiloxanes. The reaction had a broad substrate scope and showed good functional group tolerance. N-Benzoylsuccinimide and N-protected N-phenylbenzamides showed good activities in coupling reactions with phenylsiloxane. The employment of CuF2 as an activor afforded the decarbonylative products at 160 °C.