Fenofibric acid
[CAS# 42017-89-0]

Identification

• Classification: Analytical chemistry >> Analytical reagent >> Ion chromatography reagent
• Name: Fenofibric acid
• Synonyms: 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid; 2-[4'-(p-Chlorobenzoyl)phenoxy]-2-methylpropionic acid
• Molecular Formula: C₁₇H₁₅ClO₄
• Molecular Weight: 318.76
• CAS Registry Number: 42017-89-0
• EC Number: 255-626-9
• SMILES: CC(C)(C(=O)O)OC1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)Cl

Properties

• Solubility: 60 mM (DMSO), <1 mg/mL (water) (Expl.)
• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.585, Calc.^*
• Boiling Point: 486.5±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 248.0±25.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H302-H400-H413
• Precautionary Statements: P264-P270-P273-P301+P317-P330-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Reproductive toxicity	Repr.	2	H361
Carcinogenicity	Carc.	2	H351

Discovory and Applicatios

Fenofibric acid is the active metabolite of fenofibrate, a drug used primarily to lower lipid levels in the blood, particularly in patients with hyperlipidemia (elevated lipid levels) or dyslipidemia (abnormal lipid levels). It belongs to a class of drugs known as fibrates, which are primarily used to reduce triglyceride levels and increase high-density lipoprotein (HDL) cholesterol.

Fenofibric acid works by activating peroxisome proliferator-activated receptor alpha (PPAR-α), a type of nuclear receptor found in cells. Upon activation, PPAR-α influences the expression of genes that control lipid metabolism, resulting in increased fatty acid oxidation, reduced triglyceride synthesis, and increased clearance of triglyceride-rich lipoproteins. This leads to a reduction in blood triglyceride levels and an increase in HDL cholesterol, which is considered the "good" cholesterol. Additionally, fenofibric acid may lower low-density lipoprotein (LDL) cholesterol, the "bad" cholesterol, although its effect on LDL is less pronounced compared to its effects on triglycerides and HDL.

Fenofibric acid is typically used in the treatment of hypertriglyceridemia, hyperlipidemia, and mixed dyslipidemia. It is especially useful in patients with elevated triglyceride levels, which can increase the risk of cardiovascular diseases, including atherosclerosis. The drug may also be prescribed for patients with low HDL cholesterol levels, as higher HDL cholesterol is associated with a reduced risk of heart disease. Fenofibric acid is used either alone or in combination with statins, which are medications that lower LDL cholesterol, for comprehensive management of lipid disorders.

The medication is usually taken orally, typically as a capsule or tablet, with dosing depending on the severity of the lipid abnormalities and the patient's response to treatment. Fenofibric acid is typically well tolerated, although it can cause side effects in some individuals. Common side effects include gastrointestinal symptoms such as abdominal pain, nausea, and diarrhea. Less commonly, more serious side effects such as muscle pain or weakness (myopathy), liver dysfunction, and kidney impairment may occur, particularly in patients with pre-existing liver or kidney conditions. As a result, regular monitoring of liver enzymes and kidney function is recommended during treatment.

Fenofibric acid should be used with caution in individuals with a history of liver disease, kidney disease, or gallbladder disease, as it can exacerbate these conditions. Additionally, the drug may interact with other medications, including statins, increasing the risk of muscle-related side effects such as rhabdomyolysis. Patients should inform their healthcare provider about all the medications they are taking to prevent potential drug interactions.

Fenofibric acid is generally considered safe when used as prescribed, and it plays an important role in managing lipid disorders and reducing the risk of cardiovascular diseases. However, as with any medication, it is important for patients to follow their healthcare provider's recommendations and undergo regular monitoring to ensure the drug's effectiveness and safety.

References

2022. Functional and Structural Insights into Human PPARα/δ/γ Subtype Selectivity of Bezafibrate, Fenofibric Acid, and Pemafibrate. International Journal of Molecular Sciences, 23(9).
DOI: 10.3390/ijms23094726

2016. Comparison of efficacy and safety of choline fenofibrate (fenofibric acid) to micronized fenofibrate in patients of mixed dyslipidemia: A randomized, open-label, multicenter clinical trial in Indian population. Indian Journal of Endocrinology and Metabolism, 20(1).
DOI: 10.4103/2230-8210.172243

2012. Study Design, Rationale, and Baseline Characteristics: Evaluation of Fenofibric Acid on Carotid Intima-Media Thickness in Patients with Type IIb Dyslipidemia with Residual Risk in Addition to Atorvastatin Therapy (FIRST) Trial. Cardiovascular Drugs and Therapy, 26(4).
DOI: 10.1007/s10557-012-6395-z