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Fenofibrate

CAS No.
49562-28-9
Chemical Name:
Fenofibrate
Synonyms
sedufen;Fenoglide;lf-178;lipsin;Lipirex;Liposit;Nolipax;Secalip;LIPYDIL;lipidax
CBNumber:
CB8266802
Molecular Formula:
C20H21ClO4
Molecular Weight:
360.83
MDL Number:
MFCD00133314
MOL File:
49562-28-9.mol
MSDS File:
SDS
Last updated:2024-03-16 07:03:48

Fenofibrate Properties

Melting point 80-810C
Boiling point 469.8±35.0 °C(Predicted)
Density 1.177±0.06 g/cm3(Predicted)
storage temp. room temp
solubility Practically insoluble in water, very soluble in methylene chloride, slightly soluble in ethanol (96 per cent)
form powder
color off-white
Water Solubility 0.8mg/L(25 ºC)
Merck 14,3978
BCS Class 2
InChI InChI=1S/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
InChIKey YMTINGFKWWXKFG-UHFFFAOYSA-N
SMILES C(OC(C)C)(=O)C(OC1=CC=C(C(=O)C2=CC=C(Cl)C=C2)C=C1)(C)C
EWG's Food Scores 1
NCI Dictionary of Cancer Terms fenofibrate
FDA UNII U202363UOS
NCI Drug Dictionary fenofibrate
ATC code C10AB05
EPA Substance Registry System Propanoic acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-, 1-methylethyl ester (49562-28-9)

Pharmacokinetic data

Protein binding 99%
Volume of distribution 0.89
Biological half-life 20 / 140-360

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H412
Precautionary statements  P273-P501
Hazard Codes  Xn,Xi
Risk Statements  22-36/37/38
Safety Statements  36-26-24/25
WGK Germany  3
RTECS  UA2453400
HS Code  29189900
Toxicity LD50 in mice: 1600 mg/kg orally (Sornay)
NFPA 704
0
3 0

Fenofibrate price More Price(44)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1269447 Fenofibrate United States Pharmacopeia (USP) Reference Standard 49562-28-9 200mg $436 2024-03-01 Buy
Sigma-Aldrich 55443 Fenofibrate analytical standard 49562-28-9 100mg $66.9 2021-12-16 Buy
TCI Chemical F0674 Fenofibrate >98.0%(GC) 49562-28-9 5g $30 2024-03-01 Buy
TCI Chemical F0674 Fenofibrate >98.0%(GC) 49562-28-9 25g $84 2024-03-01 Buy
Sigma-Aldrich F6020 Fenofibrate ≥99%, powder 49562-28-9 5g $60.3 2024-03-01 Buy
Product number Packaging Price Buy
1269447 200mg $436 Buy
55443 100mg $66.9 Buy
F0674 5g $30 Buy
F0674 25g $84 Buy
F6020 5g $60.3 Buy

Fenofibrate Chemical Properties,Uses,Production

Chemical Properties

Crystalline Solid

Originator

Lipantyl,Fournier,France,1975

Uses

Cardiovascular disease

Uses

antihyperlipidemic

Uses

Antilipemic. It is a lipid regulating drug. Increases high density lipoprotein levels by reducing cholesteryl ester transfer protein expresion.

Uses

Fenofibrate has been used:

  • to study its effect on plasma lipids, liver phenotype and gene expression
  • to study its impact on endothelium-dependent vasodilatation of thoracic aorta
  • to administer to NASH knock-in mice along with a high fat diet (HFD) to study its effect

Definition

ChEBI: A chlorobenzophenone that is (4-chlorophenyl)(phenyl)methanone substituted by a [2-methyl-1-oxo-1-(propan-2-yloxy)propan-2-yl]oxy group at position 1 on the phenyl ring.

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.

Therapeutic Function

Antihyperlipoproteinemic

General Description

Fenofibrate, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoic acid 1-methylethyl ester (Tricor),has structural features represented in clofibrate. The primarydifference involves the second aromatic ring. This imparts agreater lipophilic character than exists in clofibrate, resultingin a much more potent hypocholesterolemic and triglycerideloweringagent. Also, this structural modification results in alower dose requirement than with clofibrate or gemfibrozil.

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.

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

storage

Store at RT

Global( 696)Suppliers
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View Lastest Price from Fenofibrate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Fenofibrate pictures 2024-03-26 Fenofibrate
49562-28-9
US $120.00-65.00 / Kg/Bag 1Kg/Bag 99% up / USP/BP/EP 20 tons Sinoway Industrial co., ltd.
Fenofibrate pictures 2024-03-16 Fenofibrate
49562-28-9
US $35.00-25.00 / kg 1kg 99.8% 200tons/year Sigma Audley
Fenofibrate pictures 2024-03-08 Fenofibrate
49562-28-9
US $10.00 / kg 1kg 99% 1000kg Nantong Guangyuan Chemicl Co,Ltd
  • Fenofibrate pictures
  • Fenofibrate
    49562-28-9
  • US $120.00-65.00 / Kg/Bag
  • 99% up / USP/BP/EP
  • Sinoway Industrial co., ltd.
  • Fenofibrate pictures
  • Fenofibrate
    49562-28-9
  • US $35.00-25.00 / kg
  • 99.8%
  • Sigma Audley
  • Fenofibrate pictures
  • Fenofibrate
    49562-28-9
  • US $10.00 / kg
  • 99%
  • Nantong Guangyuan Chemicl Co,Ltd

Fenofibrate Spectrum

2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-propanoicaci1-methylethylester isopropyl(4’-(p-chlorobenzoyl)-2-phenoxy-2-methyl)propionate isopropyl2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionate lf-178 lipantil procetofen proctofene Fenofibrate, >=99% 2-[4-[(4-chlorophenyl)-oxomethyl]phenoxy]-2-methylpropanoic acid ethyl ester ethyl 2-[4-(4-chlorophenyl)carbonylphenoxy]-2-methyl-propanoate Propanoic acid, 2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-, ethyl ester 2-[4-(4-CHLOROBENZOYL)PHENOXYL-2-METHYLPROPANOIC ACID 1-METHYLETHYL ESTER 2-[4-(4-CHLOROBENZOYL)PHENOXY]-2-METHYL-PROPANOIC ACID, 1-METHYLETHYL ESTER 2-[4-(4-CHLOROBENZOYL)PHENOXY]-2-METHYLPROPANOIC ACID ISOPROPYL ESTER 2-[4-[p-Chlorobenzoyl]]-2-methylpropionic acid isopropyl ester Isopropyl 2-[p-[p-chlorobenzoyl] phenoxy]-2-methylpropionate Lipantyl Procetofene Lipidil Supra Lipirex Liposit MeltDose Nolipax NSC 281319 Fenofibrite propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoate Elasterin Secalip 2-[p-(p-Chlorobenzoyl)phenoxy]-2-methylpropionic acid isopropyl ester LIPYDIL LIPANTHYL LABOTEST-BB LT00771982 FENOFIBRATE 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propionic acid isopropyl ester propan-2-yl 2-[4-(4-chlorophenyl)carbonylphenoxy]-2-methyl-propanoate Fenofibrate,2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid isopropyl ester Fenofibrate (200 mg) Fenofibrate API Fenofibrate COS 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropionic Acid Isopropyl Ester Isopropyl 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropionate lipidax lipifen lipoclar lipofene lipsin Felodipine Solution, 100ppm Fenofibrate Solution, 1000ppm Fenobrate 2-[4-[(4-chlorophenyl)-oxomethyl]phenoxy]-2-methylpropanoic acid propan-2-yl ester Fenofibrate CRS Fenofibrate> Fenofibrate, 98%, reagent grade Lipanty Fenofibrate,>98% Propanoic acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-, 1-methylethyl ester Fenofibrate USP/EP/BP fat fenofibrat Lipofen