Ciprofibrate CAS 52214-84-3
Introduction：Basic information about Ciprofibrate CAS 52214-84-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Ciprofibrate Basic information
| Product Name: | Ciprofibrate |
| Synonyms: | 2-[4-(2，2-Dichlom-cyclopropyl)phenoxy]-2-methy|propanoic acid;Cipml;Lipanor;Modalim;Win-35833;2-(p-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropionicacid;2-[4-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropionic acid;Ciprofibric acid |
| CAS: | 52214-84-3 |
| MF: | C13H14Cl2O3 |
| MW: | 289.15 |
| EINECS: | 257-744-6 |
| Product Categories: | API;Intracellular receptor |
| Mol File: | 52214-84-3.mol |
Ciprofibrate Chemical Properties
| Melting point | 114-116° |
| Boiling point | 401.74°C (rough estimate) |
| density | 1.2576 (rough estimate) |
| refractive index | 1.5209 (estimate) |
| storage temp. | 2-8°C |
| solubility | Practically insoluble in water, freely soluble in anhydrous ethanol, soluble in toluene. |
| pka | 3.31±0.10(Predicted) |
| form | Solid |
| color | White to Pale Beige |
| Merck | 14,2313 |
| Major Application | pharmaceutical pharmaceutical small molecule |
| InChI | InChI=1S/C13H14Cl2O3/c1-12(2,11(16)17)18-9-5-3-8(4-6-9)10-7-13(10,14)15/h3-6,10H,7H2,1-2H3,(H,16,17) |
| InChIKey | KPSRODZRAIWAKH-UHFFFAOYSA-N |
| SMILES | C(O)(=O)C(OC1=CC=C(C2CC2(Cl)Cl)C=C1)(C)C |
| CAS DataBase Reference | 52214-84-3(CAS DataBase Reference) |
| EPA Substance Registry System | Propanoic acid, 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methyl- (52214-84-3) |
Safety Information
| Hazard Codes | T |
| Risk Statements | 45 |
| Safety Statements | 53-22-36/37/39-45 |
| WGK Germany | 3 |
| RTECS | UF0880000 |
| HS Code | 29189900 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Carc. 1B |
| Description | Ciprofibrate is a potent, long-acting hypolipidemic agent related to clofibrate,bezafibrate and fenofibrate. It is effective in types IIa, IIb, IIX and IVhyperlipoproteinemias, and produces a beneficial elevation of the anti-atherogenicHDL. |
| 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. |
| Chemical Properties | Off-White to Pale Beige Solid |
| Originator | Sterling-Wintbrop (USA) |
| Uses | 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. |
| Uses | antihyperlipidemic |
| Uses | Ciprofibrate is a hypolipemic agent, related structurally to Clofibrate (C586910). Ciprofibrate is used as an antilipemic. |
| Definition | ChEBI: Ciprofibrate is a monocarboxylic acid, a member of cyclopropanes and an organochlorine compound. It has a role as an antilipemic drug. |
| Manufacturing Process | A mixture of 8 g (0.0356 mol) of p-(2,2-dichlorocyclopropyl)phenol, 11.2 g(0.28 mol) of sodium hydroxide pellets, 11 g of chloroform and 350 ml ofacetone was prepared at 0°C. The cooling bath was removed, the mixturestirred for a minute and then heated on a steam bath to reflux temperature.The reaction mixture was stirred at reflux for three hours and thenconcentrated in vacuo. The residual gum was partitioned between dilutehydrochloric acid and ether, and the ether layer was separated, dried andconcentrated in vacuo. The residual oil (14 g) was partitioned between diluteaqueous sodium bicarbonate and ether. The sodium bicarbonate solution wasacidified with concentrated hydrochloric acid and extracted with ether. Theether solution was dried over anhydrous sodium sulfate and concentrated. Theresidue (9.5 g of yellow oil) was crystallized twice from hexane to give 6.0 gof 2-[p-(2,2-dichlorocyclopropyl)phenoxy]-2-methyl propionic acid in the formof a pale cream-colored solid, MP 114°C to 116°C. |
| Brand name | LJPANOR |
| Therapeutic Function | Antihyperlipidemic |
| World Health Organization (WHO) | The safety profile of ciprofibrate is similar to that of clofibrate.See also under clofibrate in full edition. |
| Biochem/physiol Actions | Peroxisome proliferator-activated receptor α (PPARα) agonist |
| Clinical Use | Hyperlipidaemia |
| 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. |
| Metabolism | Approximately 30-75% of a single dose administered to volunteers was excreted in the urine in 72 hours, either as unchanged ciprofibrate (20-25% of the total excreted) or as a glucuronide conjugate. Subjects with moderate renal impairment excreted on average 7% of a single dose as unchanged ciprofibrate over 96 hours, compared with 6.9% in normal subjects. In subjects with severe insufficiency this was reduced to 4.7%. |
| References | [1] Patent: CN105237389, 2017, B. Location in patent: Paragraph 0077-0078 [2] Patent: CN105175250, 2016, B. Location in patent: Paragraph 0057-0058; 0068-0069; 0079-0080 |
Ciprofibrate Preparation Products And Raw materials
| Raw materials | BUTTER-->4-Propylphenol-->Sodium hydroxide-->1,1,1-TRICHLORO-2-METHYL-2-PROPANOL HEMIHYDRATE-->4-Hydroxycinnamic acid-->Carbon tetrachloride-->4-Vinylphenol-->4-Hydroxybenzaldehyde-->ethyl 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropionate |
