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Basic information

  • Name:
  • Fenofibrate

  • CAS No.:
  • 49562-28-9

  • Formula:
  • C20H21ClO4
  • 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;
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Chemistry

Molecular Structure of Fenofibrate (CAS NO.49562-28-9):

IUPAC Name: propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
Empirical Formula: C20H21ClO4
Molecular Weight: 360.8313
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 7
Polar Surface Area: 52.6Å2
Index of Refraction: 1.546
Molar Refractivity: 97.11 cm3
Molar Volume: 306.4 cm3 
Surface Tension: 40.9 dyne/cm
Density: 1.177 g/cm3
Flash Point: 165.4 °C
Melting point: 80-81°C
Enthalpy of Vaporization: 73.22 kJ/mol
Boiling Point: 469.8 °C at 760 mmHg
Vapour Pressure: 5.35E-09 mmHg at 25°C
EINECS: 256-376-3
Product Categories: Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals; Intracellular receptor
InChI
InChI=1/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
Smiles
c1(C(c2ccc(Cl)cc2)=O)ccc(OC(C(OC(C)C)=O)(C)C)cc1

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.

Production

 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.[2] 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[3]. 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).

Toxicity Data With Reference

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,

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).

Safety Profile

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

Specification

  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.

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