Ciprofibrate

Base Information

• Chemical Name: Ciprofibrate
• CAS No.: 52214-84-3
• Molecular Formula: C13H14Cl2O3
• Molecular Weight: 289.158
• Hs Code.: 2918990090
• European Community (EC) Number: 257-744-6
• NSC Number: 759617
• UNII: F8252JGO9S
• DSSTox Substance ID: DTXSID8020331
• Nikkaji Number: J10.383G
• Wikipedia: Ciprofibrate
• Wikidata: Q3496452
• NCI Thesaurus Code: C87471
• Pharos Ligand ID: AHNNWLKHZ9KC
• Metabolomics Workbench ID: 57559
• ChEMBL ID: CHEMBL557555
• Mol file: 52214-84-3.mol

Synonyms:ciprofibrate;Hyperlipen;Lipanor;Modalim;Oroxadin;Win 35,833

Chemical Property of Ciprofibrate

Chemical Property:

• Appearance/Colour: White or almost white powder
• Vapor Pressure: 5.63E-08mmHg at 25°C
• Melting Point: 114 - 118oC
• Refractive Index: 1.579
• Boiling Point: 424.9 °C at 760 mmHg
• PKA: 3.31±0.10(Predicted)
• Flash Point: 210.7 °C
• PSA: 46.53000
• Density: 1.37 g/cm³
• LogP: 3.58980
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, freely soluble in anhydrous ethanol, soluble in toluene.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 288.0319997
• Heavy Atom Count: 18
• Complexity: 333

Purity/Quality:

99% ^*data from raw suppliers

Ciprofibrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45
• Safety Statements: 53-22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C(=O)O)OC1=CC=C(C=C1)C2CC2(Cl)Cl
• Recent ClinicalTrials: Ciprofibrate and Pre-diabetes
• Recent EU Clinical Trials: Effects of ciprofibrate on myocardial insulin sensitivity in pre-diabetes
• Description: Ciprofibrate is an agonist of peroxisome proliferator-activated receptor α (PPARα; EC50 = 0.9 μM in a transactivation assay). It is selective for PPARα over PPARγ and PPARδ at 300 μM. Ciprofibrate (250 μM) induces cell cycle arrest at the G2/M and S phases in Fao rat, but not HepG2 human, hepatocellular carcinoma cells. It decreases fasting plasma levels of triglycerides and increases fasting plasma glucose levels in the apolipoprotein CIII transgenic mouse model of hypertriglyceridemia when administered at a dose of 10 mg/kg. Formulations containing ciprofibrate have been used in the treatment of hypertriglyceridemia. Ciprofibrate is a potent, long-acting hypolipidemic agent related to clofibrate, bezafibrate and fenofibrate. It is effective in types IIa, IIb, IIX and IV hyperlipoproteinemias, and produces a beneficial elevation of the anti-atherogenic HDL.
• Uses: Ciprofibrate is a hypolipemic agent, related structurally to Clofibrate (C586910). Ciprofibrate is used as an antilipemic. Peroxisome proliferator-activated receptor α (PPARα) is a ligand-activated transcription factor involved in the regulation of lipid homeostasis. Activation of PPARα results in expression of a variety of genes, particularly those involved in fatty acid β-oxidation, binding, and transport. Ciprofibrate activates PPARα with an EC50 value of 20 μM and only marginally affects PPARγ (EC50 = >300 μM). It has been shown to lower adipose tissue weight and reduce plasma insulin concentrations in obese rats and has been used clinically in the treatment of dyslipidemia. Ciprofibrate reportedly stimulates cholesteryl ester transfer protein expression and improves the flow of cholesterol through the indirect reverse cholesterol transport system, preserving plasma HDL.
• Therapeutic Function: Antihyperlipidemic
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: increased risk of myopathy with daptomycin - try to avoid concomitant use. Anticoagulants: enhances effect of coumarins and phenindione. Dose of anticoagulant should be reduced by up to 50% and readjusted by monitoring INR. Antidiabetics: may improve glucose tolerance and have an additive effect with insulin or sulphonylureas. Colchicine: possible increased risk of myopathy. Lipid-regulating drugs: increased risk of myopathy in combination with statins and ezetimibe (Do not exceed 10 mg of simvastatin and 20 mg of rosuvastatin.1 ) - avoid with ezetimibe.

Technology Process of Ciprofibrate

There total 10 articles about Ciprofibrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate (130232-51-8,130233-23-7,130233-24-8) → 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid (52214-84-3)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃; for 0.5h;

Reference yield: 90.0%

ethyl 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropionate (52179-28-9,144940-19-2,144940-25-0) → 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid (52214-84-3)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 0.5h;

Reference yield: 82.0%

→ 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid (52214-84-3)

Guidance literature:

upstream raw materials:

(-)-4-(2,2-dichlorocyclopropyl)phenol

methyl 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoate

4-Vinylphenol

ethyl 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropionate

Downstream raw materials:

2-(p-acetylphenoxy)-2-methylpropionic acid

4-(1-carboxy-1-methyl-ethoxy)-benzoic acid

2-(4-formylphenoxy)-2-methylpropanoic acid

Refernces

• 1、 -. "Synthetic method of lipid-lowering drug ciprofibrate". . . Retrieved 2017/09/01.
• 2、 -. "A new method for synthesizing cyclopropanecarboxylic Bethe". Paragraph 0057-0058; 0068-0069; 0079-0080. . Retrieved 2018/02/04.