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

General Information

Structure

Molecular Formula

C₂₀H₂₁ClO₄

Molecular Mass

360.83134

Exact Mass

360.11283683

Charge

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

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

5.277763

LogD (pH = 7.4)

5.277763

Log P

5.277763

Molar Refractivity

97.1298

Polarizability

38.178596

Polar Surface Area

52.6

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

4.86

LOG S

-5.71

Solubility (Water)

7.07e-04 g/l

Data Source

Names and Identifiers

IUPAC name

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

Synonyms

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

Brand Name

LipofeneLipidexSedufenNolipaxElasterinElasterateAntaraLipanthylLipsinLofibraProcetofenSecalipLuxacorTriglideLipirexFenogalLipoclarAnkebinProctofeneTrilipixProtolipanFenobrateTricorLipifenLipidil SupraLipantilLipositFenotardLipidilLipidil Micro

IUPAC Traditional name

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

Names and Identifiers

Registration numbers

PubChem CID

3339

PubChem SID

2427801546507371160964374

CAS Number

49562-28-9

MDL Number

MFCD00133314

EC Number

256-376-3

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

-20°C Freezer

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

German water hazard class

MSDS Link

Download link

UA2453400

Pharmacology Properties

Gene Information

human ... PPARA(5465)

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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.

TRC

F248640

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

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

Synonyms

Brand Name

IUPAC Traditional name

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

Registration numbers

PubChem CID

3339

PubChem SID

2427801546507371160964374

CAS Number

MDL Number

EC Number

Molecule Details

DB01039

Drug Groups

approved

Description

An antilipemic agent which reduces both cholesterol and triglycerides in the blood. [PubChem]

Indication

Pharmacology

Toxicity

LD₅₀=1600 mg/kg (Oral, in mice); Investigated as a teratogen and reproductive hazard.

Affected Organisms

Humans and other mammals

Absorption

Half Life

20 hours

Protein Binding

~99% (Serum protein binding)

Elimination

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

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1794

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.

References

PubChem Literature

From Data Sources

• 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)

Bioactivity

PubChem BioAssay

Properties

Safety Information

Storage Condition

-20°C

-20°C Freezer

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

German water hazard class

MSDS Link

Download link

UA2453400

Pharmacology Properties

Gene Information

human ... PPARA(5465)

Molecule

ID:911