Introduction：Basic information about Choline Fenofibrate CAS 856676-23-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Choline Fenofibrate Basic information
| Product Name: | Choline Fenofibrate |
| Synonyms: | Abt 335;Fenofibrate de choline;Trilipix;Unii-4bmh7izt98;Choline Fenofibrate;2-Hydroxy-N,N,N-triMethylethanaMiniuM 2-[4-(4-chlorobenzoyl)phenoxy]-2-Methylpropanoate;2-hydroxy-N,N,N-trimethyl, 2-{4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate;Fenofibrate Impurity 8(Choline Fenofibrate) |
| CAS: | 856676-23-8 |
| MF: | C22H28ClNO5 |
| MW: | 421.91442 |
| EINECS: | |
| Product Categories: | API;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol File: | 856676-23-8.mol |
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Choline Fenofibrate Chemical Properties
| Melting point | 210-212°C |
| storage temp. | Hygroscopic, -20°C Freezer, Under Inert Atmosphere |
| solubility | Methanol (Slightly), Water (Slightly) |
| form | Solid |
| color | White to Off-White |
| Stability: | Hygroscopic |
| Major Application | pharmaceutical (small molecule) |
| InChI | InChI=1S/C17H15ClO4.C5H14NO/c1-17(2,16(20)21)22-14-9-5-12(6-10-14)15(19)11-3-7-13(18)8-4-11;1-6(2,3)4-5-7/h3-10H,1-2H3,(H,20,21);7H,4-5H2,1-3H3/q;+1/p-1 |
| InChIKey | JWAZHODZSADEHB-UHFFFAOYSA-M |
| SMILES | OCC[N+](C)(C)C.CC(C(=O)[O-])(OC1C=CC(C(=O)C2C=CC(Cl)=CC=2)=CC=1)C |
Safety Information
| WGK Germany | WGK 3 |
| HS Code | 2923100000 |
| Storage Class | 11 - Combustible Solids |
Choline Fenofibrate Usage And Synthesis
| Description | Choline fenofibrate, a salt formulation of fenofibric acid, is a lipidregulating agent available as delayed release capsules for oral administration. It is indicated in combination with a statin to reduce TG andincrease high-density lipoprotein cholesterol (HDL-C) in patients withmixed dyslipidemia and coronary heart disease (CHD) or a CHD-riskequivalent who are optimal for statin therapy to achieve their lowdensity lipoprotein cholesterol (LDL-C) goal. In addition, cholinefenofibrate is indicated as monotherapy in patients with severehypertriglyceridemia to reduce TG, and in patients with primaryhyperlipidemia or mixed dyslipidemia to reduce elevated LDL-C, totalcholesterol, TG, apolipoprotein B, and to increase HDL-C. Fenofibric acidis also the active metabolite of fenofibrate (Tricor), which has beenpreviously marketed for the treatment of hypercholesterolemia andhypertriglyceridemia. The primary mode of action of fenofibric acidis through the activation of the nuclear transcription factor PPARa,predominantly expressed in tissues that metabolize fatty acids, such asthe liver, kidney, heart, and muscle.
On activation by binding of the fibrate, PPARa binds as heterodimers with retinoid X receptor (RXR), which subsequently recognizes and binds to specific PPARa-response elements leading to modulation of expression of the target genes. In particular, the activity of lipoprotein lipase is increased and synthesis of apoprotein C-III is decreased, which together enhance the clearance of circulating TG-rich lipoproteins. The resulting fall in TG produces an alteration in the size and composition of LDL from small dense particles to large buoyant particles. These larger particles have a greater affinity for cholesterol receptors and are catabolized rapidly. Choline fenofibriate acid is contraindicated in patients with severe renal impairment. |
| Chemical Properties | White Solid |
| Originator | Abbott (United States) |
| Uses | A new formulation of fenofibric acid, ABT-335, co-administered with statins. |
| Brand name | TriLipix |
| Side effects | The most common adverse reactions observed with the use of fenofibric acid alone or in combination with a statin are headache, back pain, nasopharyngitis, nausea, myalgia, diarrhea, and upper respiratory tract infection. |
| Synthesis | Choline To Market, To Market 2008 enofibrate is chemically derived from p-anisole in four steps through Friedel Crafts acylation with p-chlorobenzoyl chloride to the corresponding benzophenone derivative, followed by methyl ether cleavage with hydrogen bromide, alkylation of the phenolic hydroxyl group with 2-bromo-2-methylpropanoic acid using sodium hydroxide, and finally salt formation with choline. |
| References | [1] Patent: US2008/275270, 2008, A1. Location in patent: Page/Page column 3 |
Choline Fenofibrate Preparation Products And Raw materials
| Raw materials | Fenofibric acid-->Ethyl 2-bromoisobutyrate-->Isopropyl 2-bromo-2-methylpropanoate-->4-Chloro-4'-hydroxybenzophenone-->Choline chloride-->Choline hydroxide |
