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Fenofibrate(CAS No. 49562-28-9)

Fenofibrate C20H21ClO4 (cas 49562-28-9) Molecular Structure

49562-28-9 Structure

Identification and Related Records

【Iupac name】
propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
【CAS Registry number】
Fenofibrate [BAN:INN]
propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoate
Propanoic acid,2-[4-(4-chlorobenzoyl)phenoxy]- 2-methyl-,1-methylethyl ester
Isopropyl 2-(p-(p-chlorobenzoyl)phenoxy)-2-methylpropionate
Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionate
Propanoic acid, 2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-, 1-methylethyl ester
Fenofibratum [INN-Latin]
Fenofibrate (JAN)
2-(4-(4-Chlorobenzoyl)phenoxy)-2-methylpropanoic acid 1-methylethyl ester
Isopropyl (4-(p-chlorobenzoyl)-2-phenoxy-2-methyl)propionate
Lipantil (TN)
【Molecular Formula】
C20H21ClO4 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

White or yellowish crystalline powder
1.177 g/cm3
【Melting Point】
【Boiling Point】
469.8 °C at 760 mmHg
【Flash Point】
165.4 °C
0.1 mg/L (37 C)
Stable at normal temperatures and pressures.
【Storage temp】
Keep tightly closed.
【Computed Properties】
Molecular Weight:360.83134 [g/mol]
Molecular Formula:C20H21ClO4
H-Bond Donor:0
H-Bond Acceptor:4
Rotatable Bond Count:7
Exact Mass:360.112837
MonoIsotopic Mass:360.112837
Topological Polar Surface Area:52.6
Heavy Atom Count:25
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:2
Effective Rotor Count:7
Conformer Sampling RMSD:0.8
CID Conformer Count:259

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】

Hazard Codes:?HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38
R22:Harmful if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 36-26
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: UA2453400

Fenofibrate Preparations Route Dosage Form Strength Brand or Generic Name (Manufacturer) Oral Tablets 48 mg TriCor (Abbott) Oral Tablets 50 mg Triglide (Sciele) Oral Tablets 54 mg Fenofibrate Tablets (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets 145 mg TriCor (Abbott) Oral Tablets 160 mg Fenofibrate Tablets (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets 160 mg Triglide (Sciele) Oral Tablets, film-coated 54 mg Lofibra (Gate) Oral Tablets, film-coated 160 mg Lofibra (Gate)
Fenofibrate (micronized) Preparations Route Dosage Form Strength Brand or Generic Name (Manufacturer) Oral Capsules 43 mg Antara (Reliant) Oral Capsules 67 mg Fenofibrate Micronized Capsules (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Capsules 67 mg Lofibra (Gate) Oral Capsules 130 mg Antara (Reliant) Oral Capsules 134 mg Fenofibrate Micronized Capsules (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Capsules 134 mg Lofibra (Gate) Oral Capsules 200 mg Fenofibrate Micronized Capsules (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Capsules 200 mg Lifibra (Gate)
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl fenofibrate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

? Fenofibrate , with CAS number of 49562-28-9, can be called 2-(4-(4-Chlorobenzoyl)phenoxy)-2-methylpropanoic acid 1-methylethyl ester ; Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionate ; Isopropyl (4'-(p-chlorobenzoyl)-2-phenoxy-2-methyl)propionate ; Sedufen .?Fenofibrate (CAS NO.49562-28-9) is a drug of the fibrate class.?It is mainly used to reduce Cholesterol levels in patients at risk of cardiovascular disease. Like other fibrates, it reduces both low-density lipoprotein (LDL) and very low density lipoprotein (VLDL) levels, as well as increasing high-density lipoprotein (HDL) levels and reducing tryglycerides level. It also appears to have a beneficial effect on the Insulin resistance featured by the metabolic syndrome. It is used alone or in conjunction with statins in the treatment of hyperCholesterolemia and hypertriglyceridemia.

【Octanol/Water Partition Coefficient】
log Kow = 5.19 (est)

The pharmaceutical form and the strength may change from one country to another, and from one brand to another. In the United States, Tricor was reformulated in 2005 and is available in tablets of 48 and 145 mg. This reformulation is controversial and is the subject of antitrust litigation by generic drug manufacturer Teva. Also available in the United States, Lofibra is available in 54 and 160 mg tablets, as well as 67, 134, and 200 mg micronized capsules. Generic equivalents of Lofibra capsules are currently available in all three strengths in the United States. In Europe, it is available in either coated tablet or capsule; the strength range includes 67, 145, 160 and 200 mg. The differences among strengths are a result of altered bioavailability (the fraction absorbed by the body) due to particle size. For example, 200 mg can be replaced by 160 mg micronized fenofibrate. The 145 mg strength is a new strength appeared in 2005-2006 which also replaces 200 or 160 mg as the fenofibrate is nanonised (ie the particle size is below 400 nm).

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Fenofibrate is prepared from 4-chloro-4-hydroxybenzophenone either in analogy to the synthesis of clofibric acid and in the final step converted into the isopropyl ester or by alkylation with preformed isopropyl alpha-bromoisobutyrate.

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

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
【Therapeutic Uses】
Fenofibrate is used as an adjunct to dietary therapy to decrease elevated serum total and LDL-cholesterol, triglyceride, and apo B concentrations, and to increase HDL-cholesterol concentrations in the management of primary hypercholesterolemia and mixed dyslipidemia, including heterozygous familial hypercholesterolemia and other causes of hypercholesterolemia.
Fenofibrate also is used as an adjunct to dietary therapy in the management of patients with elevated serum triglyceride concentrations. Efficacy of the drug in reducing the risk of pancreatitis in patients with marked elevations in triglyceride concentrations (i.e., greater than 2000 mg/dL) has not been established. Fenofibrate is not indicated for use in patients with type I hyperlipoproteinemia who have elevated triglyceride and chylomicron concentrations but normal VLDL-cholesterol concentrations.
/EXPL THER/ Inflammation is implicated in chronic heart failure. In this study, the potential inhibitory effect of peroxisome proliferator-activated receptor-alpha (PPARalpha) activator fenofibrate on monocyte adhesion in chronic heart failure patients was investigated in vitro. ... Isolated peripheral blood mononuclear cells were collected from 36 patients (aged 65 +/- 8 years) with symptomatic chronic heart failure and from 12 healthy control subjects. The cultured human aortic endothelial cells were stimulated with or without 2 ng mL(-1) tumor necrosis factor-alpha (TNF-alpha) and the inhibitory effects of fenofibrate at 25, 50, 100 and 200 uM on endothelial mononuclear cell adhesion were tested. Furthermore, the human aortic endothelial cells were stimulated with 70% sera obtained from chronic heart failure patients and control individuals, respectively, with or without pretreatments with fenofibrate. The endothelial expression of vascular cell adhesion molecule-1 (VCAM-1) and intercellular adhesion molecule-1 (ICAM-1) was then confirmed by mRNA expression and Western blot. ... The increased adhesion of peripheral blood mononuclear cells to TNF-alpha-stimulated human aortic endothelial cells in chronic heart failure patients was reduced when the human aortic endothelial cells were pretreated with fenofibrate (31% inhibition, P = 0.0121). However, pretreatment of the isolated peripheral blood mononuclear cells collected from chronic heart failure patients with fenofibrate failed to suppress their adherence to TNF-alpha-stimulated human aortic endothelial cells. Furthermore, stimulation of cultured human aortic endothelial cells with chronic heart failure patient sera significantly increased VCAM-1 and ICAM-1 expression, which could also be inhibited by fenofibrate. The fenofibrate directly inhibits monocyte binding by TNF-alpha-activated human aortic endothelial cells, probably through preventing up-regulation of cell adhesion molecules by endothelial cells in response to inflammatory stimuli. This PPARalpha activator may have the potential to ameliorate vascular inflammation in patients with chronic heart failure. [Huang WP et al; Eur J Clin Invest. 2009 Jun 15. [Epub ahead of print]]
【Biomedical Effects and Toxicity】
Upon multiple dosing of fenofibrate, fenofibric acid steady state is achieved within 9 days. Plasma concentrations of fenofibric acid at steady state are approximately double those following a single dose. Serum protein binding was approximately 99% in normal and hyperlipidemic subjects.
The absolute bioavailability of fenofibrate cannot be determined as the compound is virtually insoluble in aqueous media suitable for injection. However, fenofibrate is well absorbed from the gastrointestinal tract. Following oral administration in healthy volunteers, approximately 60% of a single dose of radiolabelled fenofibrate appeared in urine, primarily as fenofibric acid and its glucuronate conjugate, and 25% was excreted in the feces. Peak plasma levels of fenofibric acid occur within 6 to 8 hours after administration.
After absorption, fenofibrate is mainly excreted in the urine in the form of metabolites, primarily fenofibric acid and fenofibric acid glucuronide. After administration of radiolabelled fenofibrate, approximately 60% of the dose appeared in the urine and 25% was excreted in the feces.
The metabolism and disposition of orally administered single doses of (14)C fenofibrate (isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2- methylpropionate) have been studied in rat, guinea pig, and dog. In rats, the urinary excretion of (14)C in 5 days varied from 11 to 51% of the dose and was markedly dependent upon the dose form given. The interpretation of these data in terms of factors affecting the absorption of fenofibrate from the gut is complicated by the enterohepatic recirculation of metabolites. The tissue distribution of (14)C after oral administration of an ethanolic solution of fenofibrate has been studied in the rat. The only tissues in which the concentration of (14)C exceeded that in the blood were the organs of absorption and elimination, the gut, liver, and kidneys. Guinea pigs excreted 53% of the dose in the urine in 5 days, with a further 34% in the feces, while in dogs the corresponding figures were 9% and 81%, respectively. In all three species, all the urinary metabolites were products of ester hydrolysis, and the principal excretion product was "reduced fenofibric acid" which arose by subsequent carbonyl reduction. Glucuronidation of fenofibric acid and "reduced fenofibric acid" was a very minor reaction in the rat and guinea pig and was not detected in the dog. In addition, polar unknown metabolite(s) were detected in all three species, but were not investigated further. The results are discussed in terms of the comparative disposition of fenofibrate and other hypolipidemic agents and the contribution of these findings to the safety assessment of such drugs. [Weil A et al; Drug Metab Dispos 16 (2): 302-9 (1988). Available from, as of June 1, 2009:] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
The rate constant for the vapor-phase reaction of fenofibrate with photochemically-produced hydroxyl radicals has been estimated as 2.5X10-11 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 15 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 4.4X10-3 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 50 and 5 years at pH values of 7 and 8, respectively(2). Fenofibrate contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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