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Basic Information
CAS No.: 49562-28-9
Name: Fenofibrate
Article Data: 52
Molecular Structure:
Molecular Structure of 49562-28-9 (Fenofibrate)
Formula: C20H21ClO4
Molecular Weight: 360.837
Synonyms: Fenogal;Elasterin;Liposit;Fenofibrate [BAN:INN];Lipofene;Lipantil;Elasterate;propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoate;Prestwick_217;Propanoic acid,2-[4-(4-chlorobenzoyl)phenoxy]- 2-methyl-,1-methylethyl ester;Protolipan;Luxacor;Isopropyl 2-(p-(p-chlorobenzoyl)phenoxy)-2-methylpropionate;Procetofen;Secalip;Finofibrate;Lipifen;Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionate;Ankebin;Propanoic acid, 2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-, 1-methylethyl ester;Fenofibratum [INN-Latin];FNF;Fenobrate;Triglide;Lipidil;Fenofibrate (JAN);Nolipax;LF-178;2-(4-(4-Chlorobenzoyl)phenoxy)-2-methylpropanoic acid 1-methylethyl ester;Isopropyl (4-(p-chlorobenzoyl)-2-phenoxy-2-methyl)propionate;Antara;Lipirex;Lipantil (TN);Fenofibrat;
EINECS: 256-376-3
Density: 1.177 g/cm3
Melting Point: 80-81 °C
Boiling Point: 469.8 °C at 760 mmHg
Flash Point: 165.4 °C
Solubility: 0.8mg/L(25 oC)
Appearance: Crystalline solid
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38
Safety: 36-26
PSA: 52.60000
LogP: 4.68000
Synthetic route
42017-89-0

fenofibric acid

67-63-0

isopropyl alcohol

49562-28-9

fenofibrate

Conditions
ConditionsYield
With magneticnanosolidsuperacid In cyclohexane; water at 83 - 85℃; Reagent/catalyst; Temperature;97%
Stage #1: fenofibric acid; isopropyl alcohol With thionyl chloride for 7h; Reflux;
Stage #2: With potassium carbonate In water at 60 - 65℃;
96.6%
With macroporous strong acid cation exchange resin D001 In water; toluene at 110℃;92.4%
42017-89-0

fenofibric acid

75-26-3

isopropyl bromide

49562-28-9

fenofibrate

Conditions
ConditionsYield
Stage #1: fenofibric acid With potassium carbonate In Isopropyl acetate; dimethyl sulfoxide at 20 - 90℃; for 0.75h; Industry scale; Inert atmosphere;
Stage #2: isopropyl bromide In Isopropyl acetate; dimethyl sulfoxide at 80 - 95℃; for 5.83333h;
94.9%

isopropyl 2-(4-(1-(4-chlorophenyl)-2-methoxyvinyl)phenoxy)-2-methylpropanoate

49562-28-9

fenofibrate

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper (II) carbonate hydroxide; TPGS-750-M In water at 20℃; Green chemistry;91%
51368-55-9

isopropyl 2-bromo-2‑methylpropanoate

42019-78-3

4-chloro-4'-hydroxybenzophenone

49562-28-9

fenofibrate

Conditions
ConditionsYield
With potassium hydrogencarbonate In isopropyl alcohol for 48h; Reflux;90%
Stage #1: 4-chloro-4'-hydroxybenzophenone With sodium hydroxide In butanone for 1h; Reflux;
Stage #2: isopropyl 2-bromo-2‑methylpropanoate In butanone for 8h; Reflux;
90%
Stage #1: 4-chloro-4'-hydroxybenzophenone With potassium hydrogencarbonate In isopropyl alcohol at 25℃; for 0.166667h;
Stage #2: isopropyl 2-bromo-2‑methylpropanoate In isopropyl alcohol at 90℃; for 48h;
90%
1375008-18-6

isopropyl 2-(4-iodophenoxy)-2-methylpropanoate

1679-18-1

4-Chlorophenylboronic acid

13939-06-5, 199620-15-0

molybdenum hexacarbonyl

49562-28-9

fenofibrate

Conditions
ConditionsYield
With potassium phosphate; palladium(II) trifluoroacetate In water; acetonitrile at 50℃; for 6h; Suzuki Coupling; Inert atmosphere; Sealed tube;90%
201230-82-2

carbon monoxide

1375008-18-6

isopropyl 2-(4-iodophenoxy)-2-methylpropanoate

1679-18-1

4-Chlorophenylboronic acid

49562-28-9

fenofibrate

Conditions
ConditionsYield
With potassium carbonate; palladium dichloride at 80℃; for 16h; Sealed tube;89%
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; triethylamine In 1,4-dioxane at 80℃; for 20h; Inert atmosphere; Sealed tube; Cooling with ice;80%
With potassium carbonate; triphenylphosphine; palladium dichloride at 80℃; for 18h;65 %Chromat.
1375008-18-6

isopropyl 2-(4-iodophenoxy)-2-methylpropanoate

1679-18-1

4-Chlorophenylboronic acid

82102-37-2

9-methyl-9H-fluorene-9-carbonyl chloride

49562-28-9

fenofibrate

Conditions
ConditionsYield
Stage #1: 9-methyl-9H-fluorene-9-carbonyl chloride With N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate at 80℃;
Stage #2: isopropyl 2-(4-iodophenoxy)-2-methylpropanoate; 4-Chlorophenylboronic acid With potassium carbonate; palladium dichloride at 80℃;
84%
1581307-35-8

isopropyl 2-(4-bromophenoxy)-2-methylpropanoate

5123-08-0

2-(4-chloro-phenyl)-[1,3,6,2]dioxazaborocane

82102-37-2

9-methyl-9H-fluorene-9-carbonyl chloride

49562-28-9

fenofibrate

Conditions
ConditionsYield
With palladium(II) acetylacetonate; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate; di(1-adamantyl)-N-butylphosphine hydroiodide In water; N,N-dimethyl-formamide; toluene at 80℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;83%
637-87-6

1-Chloro-4-iodobenzene

201230-82-2

carbon monoxide

C13H18O3

49562-28-9

fenofibrate

Conditions
ConditionsYield
With 2,6-di-tert-butyl-pyridine; bis(η3-allyl-μ-chloropalladium(II)); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; under 22801.5 Torr; for 24h; Reagent/catalyst; Inert atmosphere; Sealed tube; Glovebox; Schlenk technique;83%
61001-99-8

4-((4-chlorophenyl)(hydroxy)methyl)phenol

49562-28-9

fenofibrate

Conditions
ConditionsYield
With oxygen; Langlois reagent In acetonitrile at 25℃; under 760.051 Torr; for 12h; Irradiation;83%
Downstream Products
61001-99-8
42017-89-0
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History

 Fenofibrate (CAS NO.49562-28-9) was discovered by Groupe Fournier SA, before it was acquired in 2005 by Solvay Pharmaceutical, a business unit owned by the Belgian corporation, Solvay S.A. Fenofibrate is sold under the brand name Tricor and Trilipix by Abbott Labs, Lipofen by Kowa Pharmaceuticals America Inc, Lofibra by Teva, Lipanthyl and Lipidil by Solvay Pharmaceutical and Fenocor-67 by Ordain Health Care Pvt Ltd.

Consensus Reports

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).

Specification

Fenofibrate, with the IUPAC Name of propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate, is one kind of drug. This chemical belongs to the Product Categories which include Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals; Intracellular receptor. 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.

Physical properties about Fenofibrate are: (1)ACD/LogP: 5.801; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.80; (4)ACD/LogD (pH 7.4): 5.80; (5)ACD/BCF (pH 5.5): 15087.66; (6)ACD/BCF (pH 7.4): 15087.66; (7)ACD/KOC (pH 5.5): 34091.39; (8)ACD/KOC (pH 7.4): 34091.39; (9)#H bond acceptors: 4; (10)#Freely Rotating Bonds: 7; (11)Index of Refraction: 1.547; (12)Molar Refractivity: 97.116 cm3; (13)Molar Volume: 306.449 cm3; (14)Polarizability: 38.5 10-24cm3; (15)Surface Tension: 40.9819984436035 dyne/cm; (16)Density: 1.177 g/cm3; (17)Flash Point: 165.356 °C; (18)Enthalpy of Vaporization: 73.22 kJ/mol; (19)Boiling Point: 469.774 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C

When you are using Fenofibrate, please be cautious about it as the following:
1.Wear suitable protective clothing;
2. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You could convert the following datas into the molecular structure:
(1)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;
(2)InChIKey=YMTINGFKWWXKFG-UHFFFAOYSA-N;
(3)Smilesc1(C(c2ccc(Cl)cc2)=O)ccc(OC(C(OC(C)C)=O)(C)C)cc1

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 4gm/kg (4000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 23(Suppl,
hamster LD50 oral > 5gm/kg (5000mg/kg)   American Journal of Medicine. Vol. 83(Suppl,
mouse LD50 oral 1600mg/kg (1600mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 885, 1976.
rat LD50 oral > 2gm/kg (2000mg/kg) LIVER: OTHER CHANGES Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 23(Suppl,