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Fenofibrate

CAS No.49562-28-9
Chemical Name:Fenofibrate
CBNumber:CB8266802
Molecular Formula:C20H21ClO4
Formula Weight:360.83
MOL File:49562-28-9.mol

Fenofibrate Property

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)
UNSPSC Code 41116107
NACRES NA.77

Safety

Hazard Codes :Xn,Xi
Risk Statements :22-36/37/38
Safety Statements :36-26-24/25
WGK Germany :3
RTECS :UA2453400
HS Code :29189900
Hazardous Substances Data :49562-28-9(Hazardous Substances Data)
Toxicity :LD50 in mice: 1600 mg/kg orally (Sornay)

NFPA 704:

	0
3		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H412
Precautionary statements P273-P501

Fenofibrate Price More Price(8)

Brand: Sigma-Aldrich(India)
Product number: F6020
Product name : Fenofibrate
Purity: ≥99%, powder
Packaging: 5G
Price: ₹5975.4
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: PHR1246
Product name : Fenofibrate
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 500MG
Price: ₹10695.1
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: F6020
Product name : Fenofibrate
Purity: ≥99%, powder
Packaging: 25G
Price: ₹18142.7
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: F6020
Product name : Fenofibrate
Purity: ≥99%, powder
Packaging: 100G
Price: ₹54601.3
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 55443
Product name : Fenofibrate
Purity: analytical standard
Packaging: 100MG
Price: ₹6354.28
Updated: 2022/06/14
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Fenofibrate Chemical Properties,Usage,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