Fenofibric acid CAS 42017-89-0
Fenofibric acid Basic information
| Product Name: | Fenofibric acid |
| Synonyms: | 2-[4-(4-CHLOROBENZOYL)PHENOXY]-2-METHYLPROPANOIC ACID;LABOTEST-BB LT00239222;FENOFIBRIC ACID;SALOR-INT L498335-1EA;2-[4-(4-CHLORO-BENZOYL)-PHENOXY]-2-METHYL-PROPIONIC ACID (FENOFIBRIC ACID);2-[4-(4-CHLOROBENBONYZOYL)PHENOXY)-2-METHYLPROPIONIC ACID;2-[4'-(p-Chlorobenzoyl)phenoxy]-2-methylpropionic acid;FENOFIBRATE ACID |
| CAS: | 42017-89-0 |
| MF: | C17H15ClO4 |
| MW: | 318.75 |
| EINECS: | 255-626-9 |
| Product Categories: | JANUVIA;Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;pharmacetical;Aromatics |
| Mol File: | 42017-89-0.mol |
Fenofibric acid Chemical Properties
| Melting point | 177-179°C |
| Boiling point | 486.5±35.0 °C(Predicted) |
| density | 1.286±0.06 g/cm3(Predicted) |
| storage temp. | 2-8°C |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| pka | 3.09±0.10(Predicted) |
| form | powder |
| color | White to Off-White |
| BRN | 2058973 |
| Major Application | forensics and toxicology pharmaceutical (small molecule) |
| 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) |
| InChIKey | MQOBSOSZFYZQOK-UHFFFAOYSA-N |
| SMILES | C(O)(=O)C(OC1=CC=C(C(=O)C2=CC=C(Cl)C=C2)C=C1)(C)C |
| CAS DataBase Reference | 42017-89-0(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn,N |
| Risk Statements | 36/37/38-50/53-22 |
| Safety Statements | 26-36/37/39-61-60-24/25 |
| RIDADR | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| RTECS | UA2453000 |
| HazardClass | 9 |
| PackingGroup | III |
| HS Code | 29189900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 |
| Toxicity | LD50 oral in rat: 1242mg/kg |
| Chemical Properties | Fenofibric acid is a white to almost white crystalline powder that is stable under ordinary conditions and has a melting point of 179 – 183°C. Its empirical formula is C17H15ClO4 and molecular weight 318.75. Fenofibric acid is insoluble in water; its solubility increases with pH in buffered media. |
| Uses | Fenofibric acid, the active metabolite of fenofibrate. Increases Apolipoprotein A-Iediated High-Density Lipoprotein Biogenesis by enhancing transcription of ATP-Binding cassette transporter A1 gene in a liver X receptorependent manner |
| Uses | Fenofibric acid, the active metabolite of fenofibrate. Increases Apolipoprotein A-I–Mediated High-Density Lipoprotein Biogenesis by enhancing transcription of ATP-Binding cassette transporter A1 gene in a liver X receptor–dependent manner. |
| Uses | DPP4 inhibitor, antidiabetic |
| Definition | ChEBI: A monocarboxylic acid that is 2-methylpropanoic acid substituted by a 4-(4-chlorobenzoyl)phenoxy group at position 2. It is a metabolite of the drug fenofibrate. |
| Synthesis | 1159999-13-9 42017-89-0 General procedure for the synthesis of fenofibric acid from compound (CAS:1159999-13-9): to a solution of compound 104 (5.00 g, 12.2 mmol) in ethanol (150 mL) was added a solution of potassium hydroxide (2.74 g, 48.9 mmol) in ethanol (50 mL). The reaction mixture was heated to reflux and stirred for 16 hours. Upon completion of the reaction, ethanol was removed under vacuum and water (200 mL) was added to the residue. The aqueous solution was washed with ether (2 x 100 mL) to remove nonpolar impurities, followed by acidification of the aqueous solution with 2N HCl to pH 1. The acidified aqueous solution was extracted with ethyl acetate (2 x 150 mL), the organic phases were combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to give compound 105 (3.57 g, 91% yield) as an off-white solid . The product was characterized by 1H NMR (300 MHz, CD3OD): δ 7.75-7.70 (m, 4H), 7.52 (d, J = 8.6 Hz, 2H), 6.96 (d, J = 9.0 Hz, 2H), 1.65 (s, 6H). |
| Metabolism | Fenofibric acid is primarily conjugated with glucuronic acid and then excreted in urine. A small amount of fenofibric acid is reduced at the carbonyl moiety to a benzhydrol metabolite, which is, in turn, conjugated with glucuronic acid and excreted in urine. In vitro and in vivo metabolism data indicate that fenofibric acid does not undergo oxidative metabolism (e.g. cytochrome P450) to a significant extent. The enzymes CYP1A2, CYP2A6, CYP2B6, CYP2C8, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A4 do not play a role in the metabolism of fenofibric acid. |
| References | [1] Patent: WO2009/73138, 2009, A2. Location in patent: Page/Page column 81-82 |
Fenofibric acid Preparation Products And Raw materials
| Raw materials | Propanoic acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-, phenylmethyl ester-->2-(4-iodophenoxy)-2-methylpropanoic acid-->FENOFIBRIC ACID ETHYL ESTER-->Fenofibrate-->4-Chloro-4'-hydroxybenzophenone-->4-Chlorobenzoyl chloride-->4-Chlorophenylboronic acid-->Acetone-->Chloroform-->Anisole-->2-Bromo-2-methylpropionic acid |
| Preparation Products | Benzenemethanol, 4-chloro-α-[4-(2-hydroxy-1,1-dimethylethoxy)phenyl]- |
