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Basic information

  • Name:
  • Fenofibric acid

  • CAS No.:
  • 42017-89-0

  • Molecular Structure:
  • Formula:
  • C17H15ClO4
  • Molecular Weight:
  • 318.75
  • Synonyms:
  • 2-[4'-(p-Chlorobenzoyl)phenoxy]-2-methylpropionic acid;2-[p-(p-Chlorobenzoyl)phenoxy]-2-methylpropionic acid;FNF acid;LF 153;LF 178 acid;NSC 281318;Procetofenic acid;a-1081;2-(4-(4-Chlorobenzoyl)phenoxy)-2-methylpropanoic acid;Propanoic acid,2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-;
  • EINECS:
  • 255-626-9
  • Density:
  • 1.287 g/cm3
  • Melting Point:
  • 177-179 °C
  • Boiling Point:
  • 486.457 °C at 760 mmHg
  • Flash Point:
  • 248.001 °C
  • Appearance:
  • white to off-white solid
  • Risk Codes:
  • 36/37/38
  • Safety Description:
  • 26-36/37/39 Details

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History

From the Department of Biochemistry, Cell Biology, and Metabolism (R.A., S.Y.), Nagoya City University Graduate School of Medical Sciences, Japan; Research and Development Institute (R.A.), Grelan Pharmaceutical Co., Tokyo, Japan; Division of Biosignaling (N.T., T.N.-M.), National Institute of Health Sciences, Tokyo, Japan; and Division of Applied Life Sciences (K.U.), Graduate School of Agriculture, Kyoto University, Japan.

Consensus Reports

 Fenofibric acid increased transcription of ABCA1 gene in a liver X receptor–dependent manner. Fibrates are widely used drugs to reduce plasma triglyceride and increase high-density lipoprotein. Their active forms, fibric acids, are peroxisome proliferator-activated receptor- activators, but no direct evidence has been demonstrated for their activation of ATP-binding cassette transporter A1 (ABCA1) in relation to clinically used fibrates. We investigated the reaction of fenofibric acid in this regard, finding that fenofibric acid increased transcription of ABCA1 gene in n liver X receptor–dependent manner.

Analytical Methods

Fenofibric acid was examined for the effect of increase of ABCA1 activity. It enhanced ABCA1 gene transcription and its protein level in macrophage cell line cells and fibroblasts and increased apolipoprotein A-I–mediated cellular lipid release, all in a dose-dependent manner. Enhancement of the gene transcription was examined by using a reporter assay system for liver X receptor responsive element (LXRE) and its inactive mutant. The results demonstrated that the effect of fenofibric acid is dependent on active LXRE.

Specification

The Fenofibric acid, with the CAS registry number 42017-89-0, is also known as 2-[4'-(p-Chlorobenzoyl)phenoxy]-2-methylpropionic acid. It belongs to the product categories of Pharmacetical; Various Metabolites and Impurities; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals; Aromatics. Its EINECS number is 255-626-9. This chemical's molecular formula is C17H15ClO4 and molecular weight is 318.75. What's more, its systematic name is 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid. Its classification codes are: (1)Anticholesteremic Agents; (2)Antilipemic agents; (3)Antimetabolites; (4)Drug / Therapeutic Agent. This chemical is used as pharmaceutical intermediates and intermediate of fenofibrate. It is the active metabolite of fenofibrate.

Physical properties of Fenofibric acid are: (1)ACD/LogP: 3.992; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.60; (4)ACD/LogD (pH 7.4): 0.35; (5)ACD/BCF (pH 5.5): 2.55; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 14.17; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 63.6 Å2; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 83.048 cm3; (15)Molar Volume: 247.696 cm3; (16)Polarizability: 32.923×10-24cm3; (17)Surface Tension: 49.10 dyne/cm; (18)Density: 1.287 g/cm3; (19)Flash Point: 248.001 °C; (20)Enthalpy of Vaporization: 79.223 kJ/mol; (21)Boiling Point: 486.457 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c1ccc(Cl)cc1)c2ccc(OC(C(=O)O)(C)C)cc2
(2)Std. InChI: InChI=1S/C17H15ClO4/c1-17(2,16(20)21)22-14-9-5-12(6-10-14)15(19)11-3-7-13(18)8-4-11/h3-10H,1-2H3,(H,20,21)
(3)Std. InChIKey: MQOBSOSZFYZQOK-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 885, 1976.
mouse LD50 oral 1200mg/kg (1200mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 885, 1976.
rat LD50 intravenous 313mg/kg (313mg/kg) LUNGS, THORAX, OR RESPIRATION: PLEURAL THICKENING

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 23.
rat LD50 oral 1242mg/kg (1242mg/kg)   Drugs of the Future. Vol. 7, Pg. 229, 1982.

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