CAS 42017-89-0|Fenofibric acid
Introduction：Basic information about CAS 42017-89-0|Fenofibric acid, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Fenofibric acid | ||
|---|---|---|---|
| CAS Number | 42017-89-0 | Molecular Weight | 318.752 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 486.5±35.0 °C at 760 mmHg |
| Molecular Formula | C17H15ClO4 | Melting Point | 176--179ºC |
| MSDS | ChineseUSA | Flash Point | 248.0±25.9 °C |
| Symbol | GHS07, GHS09 | Signal Word | Warning |
Names
| Name | fenofibric acid |
|---|---|
| Synonym | More Synonyms |
Fenofibric acid BiologicalActivity
| Description | Fenofibric acid, an active metabolite of fenofibrate, is a PPAR activitor, with EC50s of 22.4 µM, 1.47 µM, and 1.06 µM for PPARα, PPARγ and PPARδ, respectively; Fenofibric acid also inhibits COX-2 enzyme activity, with an IC50 of 48 nM. |
|---|---|
| Related Catalog | Research Areas >>Metabolic Disease |
| Target | PPARδ:1.06 μM (EC50) PPARγ:1.47 μM (EC50) PPARα:22.4 μM (EC50) COX-2:48 μM (IC50) |
| In Vitro | Fenofibric acid is a PPAR activitor, with EC50s of 22.4 µM, 1.47 µM, and 1.06 µM for PPARα, PPARγ and PPARδ, respectively[1]. Fenofibric acid (10, 25, 50, 75, and 100 nM) dose-dependently inhibits COX-2 enzyme, with IC50 of 48 nM[2]. Fenofibric acid (500 nM) reduces abundance of AOX1 protein in HepG2 cells[3]. Fenofibric acid (100 µM) decreases JNK1/2, c-Jun, and p38 MAPK phosphorylation, and prevents the accumulation of reactive oxygen species, endoplasmic reticulum (ER) stress and disruption of blood retinal barrier (BRB) in response to the combination of high-glucose (HG) and hypoxia in ARPE-19 cells. Fenofibric acid (100 µM) activates IGF-IR/Akt/ERK1/2-mediated survival signaling pathways in ARPE-19 cells under HG conditions and hypoxia[4]. |
| In Vivo | Fenofibric acid (1, 5, 10 mg/kg, p.o.) shows anti-inflammatory activity in Wistar rats with acute inflammation induced by carrageenan[2]. |
| Cell Assay | ARPE-19 cells are cultured under normoglycemic (5.5 mM D-glucose) or hyperglycemic (25 mM D-glucose) conditions for 18 days at 37°C under 5% (v/v) CO2 in medium DMEM/F12 supplemented with 10% (v/v) fetal serum (FS) and penicillin/streptomycin. ARPE-19 cells are used and the media is changed every 3-4 days. The conditions tested are: (1) Control cells which are maintained in 5.5 mM D-glucose (normal glucose) for 18 days. (2) Cells cultured in 5.5 mM D-glucose treated with 100 µM Fenofibric acid for 72 h (days 16, 17, and 18; 1 application/day). (3) Cells cultured as in (1) or (2) and submitted to hypoxia (1% oxygen) for the last 6 or 24 h. (4) Cells maintained in 25 mM D-glucose (HG) for 18 days. (5) Cells cultured in 25 mM D-glucose treated with 100 µM Fenofibric acid for 72 h (days 16, 17, and 18; 1 application/day). (6)Cells cultured as in (4) or (5) and submitted to hypoxia (1% oxygen) for the last 6 or 24 h[4]. |
| Animal Admin | The anti-inflammatory activity of fenofibrate and its active metabolite fenofibric acid is assessed by injecting 0.1 mL of 1% carrageenan solution prepared in saline (sub-plantar) to the right hind paw of the rats. Rats are divided into 6 groups of six animals each. The first group serves as negative control and receives 1% tween-80 in distilled water, 10 mL/kg body mass. Group 2 and 3 receive a single dose of fenofibrate and standard drug diclofenac at 10 mg/kg body mass, whereas groups 4, 5, and 6 receive 3 doses of Fenofibric acid at 1, 5, and 10 mg/kg body mass, respectively. All the drugs are given orally using gavages 60 min before the injection of 0.1 mL of 1% carrageenan through sub-plantar route. The volume of oedema of test and control groups is measured using plethysmometer at 0, 1, 2, and 3 h after induction of inflammation[2]. |
| References | [1]. Dietz M, et al. Comparative molecular profiling of the PPARα/γ activator aleglitazar: PPAR selectivity, activity and interaction with cofactors. ChemMedChem. 2012 Jun;7(6):1101-11. [2]. Prasad GS, et al. Anti-inflammatory activity of anti-hyperlipidemic drug, fenofibrate, and its phase-I metabolite fenofibric acid: in silico, in vitro, and in vivo studies. Inflammopharmacology. 2017 Dec 13. [3]. Neumeier M, et al. Aldehyde oxidase 1 is highly abundant in hepatic steatosis and is downregulated by adiponectin and fenofibric acid in hepatocytes in vitro. Biochem Biophys Res Commun. 2006 Nov 24;350(3):731-5. Epub 2006 Sep 27. [4]. Miranda S, et al. Beneficial effects of fenofibrate in retinal pigment epithelium by the modulation of stress and survival signaling under diabetic conditions. J Cell Physiol. 2012 Jun;227(6):2352-62. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 486.5±35.0 °C at 760 mmHg |
| Melting Point | 176--179ºC |
| Molecular Formula | C17H15ClO4 |
| Molecular Weight | 318.752 |
| Flash Point | 248.0±25.9 °C |
| Exact Mass | 318.065887 |
| PSA | 63.60000 |
| LogP | 3.86 |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.585 |
| InChIKey | MQOBSOSZFYZQOK-UHFFFAOYSA-N |
| SMILES | CC(C)(Oc1ccc(C(=O)c2ccc(Cl)cc2)cc1)C(=O)O |
| Storage condition | -20°C Freezer |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1242 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 7,229,1982
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 313 mg/kg
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - pleural thickening
- REFERENCE :
- YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 23(Suppl 4),S873,1995
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1200 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,885,1976
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 500 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,885,1976
Safety Information
| Symbol | GHS07, GHS09 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302-H410 |
| Precautionary Statements | P273-P501 |
| Hazard Codes | Xn,N |
| Risk Phrases | R36/37/38 |
| Safety Phrases | 26-36/37/39 |
| RIDADR | UN 3077 9 / PGIII |
| RTECS | UA2453000 |
| HS Code | 2918990090 |
Customs
| HS Code | 2918990090 |
|---|---|
| Summary | 2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0% |
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Synonyms
| Procetofenic acid |
| 2-(4'-(p-chlorobenzoyl)phenoxy)-2-methylpropionic acid |
| 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methyl-propanoic acid |
| Fibricor |
| Propanoic acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl- |
| Fenofibric acid |
| Fenofibrate Related Compound B |
| 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid |
| Fenofibrate impurity B |
| EINECS 255-626-9 |
| MFCD00792461 |
| 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropionic acid |
| 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid |
