CAS 49562-28-9|propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate|Fenofibratum [INN-Latin]|Lipofene|Lipidex|FNF|Sedufen|Nolipax|Elasterin|Elasterate|Antara|Lipanthyl|Lipsin|Lofibra|Procet...

基本信息

化学结构

分子式

C₂₀H₂₁ClO₄

分子量

360.83134

精确质量

360.11283683

电荷

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

Canonic Smiles

CC(OC(=O)C(Oc1ccc(cc1)C(=O)c1ccc(cc1)Cl)(C)C)C

Isomeric Smiles

Clc1ccc(C(=O)c2ccc(OC(C)(C)C(=O)OC(C)C)cc2)cc1

计算属性

JChem

质子受体

质子供体

LogD (pH = 5.5)

5.277763

LogD (pH = 7.4)

5.277763

Log P

5.277763

摩尔折射率

97.1298

极化性

38.178596

极化表面积

52.6

可自由旋转的化学键

里宾斯基五规则

false

ALOGPS 2.1

Log P

4.86

LOG S

-5.71

溶解度

7.07e-04 g/l

数据来源

名称和标识

IUPAC标准名

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

别名

Fenofibratum [INN-Latin]FNFFenofibric acidFenofibrateFinofibrateFenofibrato [INN-Spanish]AntaraLipofenFibricorFenoglideFenofibrate2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid isopropyl esterIsopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate2-[4-(4-Chlorobenzoyl)phenoxy]-2-methyl-propanoic Acid 1-Methylethyl EsterLipositLipantilLipoclarLipsinNSC 281319LipofeneLipanthylMeltDoseProcetofenLF 178NolipaxLipirexLipidil SupraProcetofene

商标名

LipofeneLipidexSedufenNolipaxElasterinElasterateAntaraLipanthylLipsinLofibraProcetofenSecalipLuxacorTriglideLipirexFenogalLipoclarAnkebinProctofeneTrilipixProtolipanFenobrateTricorLipifenLipidil SupraLipantilLipositFenotardLipidilLipidil Micro

IUPAC传统名

isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate antara

名称和标识

数据登录号

PubChem CID

3339

PubChem SID

2427801546507371160964374

CAS号

49562-28-9

MDL号

MFCD00133314

EC号

256-376-3

数据登录号

化合物性质

安全信息

药理学性质

相关基因信息

human ... PPARA(5465)

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

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.

TRC

F248640

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

描述信息

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Fenofibrate

• Chaput, et al.: Lipids, 34, 497 (1976)

• Sornay, R., et al.: Arzneim.-Forsch., 26, 885 (1976)

• Wulfert, W., et al.: Artery, 9, 120 (1976)

参考文献