propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate

• ChemBase ID: 911
• Molecular Formular: C20H21ClO4
• Molecular Mass: 360.83134
• Monoisotopic Mass: 360.11283683
• SMILES: Clc1ccc(C(=O)c2ccc(OC(C)(C)C(=O)OC(C)C)cc2)cc1
• Canonical SMILES: CC(OC(=O)C(Oc1ccc(cc1)C(=O)c1ccc(cc1)Cl)(C)C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
• IUPAC Traditional name: antara; isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
• Brand Name: Ankebin; Antara; Elasterate; Elasterin; Fenobrate; Fenogal; Fenotard; Lipanthyl; Lipantil; Lipidex; Lipidil; Lipidil Micro; Lipidil Supra; Lipifen; Lipirex; Lipoclar; Lipofene; Liposit; Lipsin; Lofibra; Luxacor; Nolipax; Procetofen; Proctofene; Protolipan; Secalip; Sedufen; Tricor; Triglide; Trilipix
• Synonyms: 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methyl-propanoic Acid 1-Methylethyl Ester; LF 178; Lipanthyl; Lipantil; Lipidil Supra; Lipirex; Lipoclar; Lipofene; Liposit; Lipsin; MeltDose; NSC 281319; Nolipax; Procetofen; Procetofene; 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid isopropyl ester; Fenofibrate; Fenofibrato [INN-Spanish]; Fenofibratum [INN-Latin]; FNF; Finofibrate; Fenofibric acid; Fenofibrate; Antara; Fenoglide; Fibricor; Lipofen; Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

Database IDs

• CAS Number: 49562-28-9
• EC Number: 256-376-3
• MDL Number: MFCD00133314
• PubChem SID: 160964374; 46507371; 24278015
• PubChem CID: 3339

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.277763
• LogD (pH = 7.4): 5.277763
• Log P: 5.277763
• Molar Refractivity: 97.1298 cm^3
• Polarizability: 38.178596 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.86
• LOG S: -5.71
• Solubility (Water): 7.07e-04 g/l

PROPERTIES

Physical Property

• Solubility: 0.25mg/ml at 25 oC; Acetone; Benzene; Chloroform; Ether
• Apperance: off-white powder; White Solid
• Melting Point: 80-81°C
• Hydrophobicity(logP): 5.3

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: UA2453400
• German water hazard class: 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... PPARA(5465)

Product Information

• Purity: ≥99%; 95+%; 97%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C20H21ClO4

DETAILS

DrugBank - DB01039

• Drug Groups: approved
• Description: An antilipemic agent which reduces both cholesterol and triglycerides in the blood. [PubChem]
• Indication: For use as adjunctive therapy to diet to reduce elevated LDL-C, Total-C,Triglycerides and Apo B, and to increase HDL-C in adult patients with primary hypercholesterolemia or mixed dyslipidemia (Fredrickson Types IIa and IIb)
• Pharmacology: Fenofibrate is a lipid regulating agent indicated as adjunctive therapy to diet to reduce elevated LDL-C, Total-C,Triglycerides and Apo B, and to increase HDL-C in adult patients with primary hypercholesterolemia or mixed dyslipidemia (Fredrickson Types IIa and IIb). Fenofibrate is also indicated as adjunctive therapy to diet for treatment of adult patients with hypertriglyceridemia (Fredrickson Types IV and V hyperlipidemia). Fenofibric acid, the active metabolite of Fenofibrate, produces reductions in total cholesterol, LDL cholesterol, apolipoprotein B, total triglycerides and triglyceride rich lipoprotein (VLDL) in treated patients. In addition, treatment with fenofibrate results in increases in high density lipoprotein (HDL) and apoproteins apoAI and apoAII.
• Toxicity: LD₅₀=1600 mg/kg (Oral, in mice); Investigated as a teratogen and reproductive hazard.
• Affected Organisms: Humans and other mammals
• Absorption: Fenofibrate is well absorbed from the gastrointestinal tract. After absorption, fenofibrate is mainly excreted in the urine in the form of metabolites, primarily fenofibric acid and fenofibric acid glucuronide
• Half Life: 20 hours
• Protein Binding: ~99% (Serum protein binding)
• Elimination: Fenofibric acid is primarily conjugated with glucuronic acid and then excreted in urine. 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.
• Distribution: * 95 L [moderate renal impairment (creatinine clearance of 50 to 90 mL/min)]; * 30 L [healthy adults]
• Clearance: * 1.2 L/h [Eldery]
• References: Wysocki J, Belowski D, Kalina M, Kochanski L, Okopien B, Kalina Z: Effects of micronized fenofibrate on insulin resistance in patients with metabolic syndrome. Int J Clin Pharmacol Ther. 2004 Apr;42(4):212-7. [Pubmed] ; Keech A, Simes RJ, Barter P, Best J, Scott R, Taskinen MR, Forder P, Pillai A, Davis T, Glasziou P, Drury P, Kesaniemi YA, Sullivan D, Hunt D, Colman P, d'Emden M, Whiting M, Ehnholm C, Laakso M: Effects of long-term fenofibrate therapy on cardiovascular events in 9795 people with type 2 diabetes mellitus (the FIELD study): randomised controlled trial. Lancet. 2005 Nov 26;366(9500):1849-61. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1794

Research Area: Cardiovascular Disease
Biological Activity:
Fenofibrate (Tricor, Trilipix) is a compound of the fibrate class and fibric acid derivative. Fenofibrate (Tricor, Trilipix) is mainly used to reduce cholesterol levels in patients at risk of cardiovascular disease. Like other fibrates, fenofibrate (Tricor, Trilipix) 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. Fenofibrate (Tricor, Trilipix) also appears to have a beneficial effect on the insulin resistance featured by the metabolic syndrome. Fenofibrate (Tricor, Trilipix) is used alone or in conjunction with statins in the treatment of hypercholesterolemia and hypertriglyceridemia. [1]

Sigma Aldrich - F6020

Biochem/physiol Actions
PPARα agonist; lipid regulating drug. Increases high density lipoprotein levels by reducing cholesteryl ester transfer protein expression.

Toronto Research Chemicals - F248640

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

REFERENCES

• Wysocki J, Belowski D, Kalina M, Kochanski L, Okopien B, Kalina Z: Effects of micronized fenofibrate on insulin resistance in patients with metabolic syndrome. Int J Clin Pharmacol Ther. 2004 Apr;42(4):212-7. Pubmed
• Keech A, Simes RJ, Barter P, Best J, Scott R, Taskinen MR, Forder P, Pillai A, Davis T, Glasziou P, Drury P, Kesaniemi YA, Sullivan D, Hunt D, Colman P, d'Emden M, Whiting M, Ehnholm C, Laakso M: Effects of long-term fenofibrate therapy on cardiovascular events in 9795 people with type 2 diabetes mellitus (the FIELD study): randomised controlled trial. Lancet. 2005 Nov 26;366(9500):1849-61. Pubmed
• http://en.wikipedia.org/wiki/Fenofibrate
• Sornay, R., et al.: Arzneim.-Forsch., 26, 885 (1976)
• Wulfert, W., et al.: Artery, 9, 120 (1976)
• Chaput, et al.: Lipids, 34, 497 (1976)