Ciprofibric acid
ciprofibrate
CAS: 52214-84-3
Molecular Formula: C13H14Cl2O3
Ciprofibric acid - Names and Identifiers
| Name | ciprofibrate |
| Synonyms | Cipml Modalim Lipanor Win-35833 CCRIS 173 WIN 35833 BRN 1984981 ciprofibrate Ciprofibrato Ciprofibratum UNII-F8252JGO9S Ciprofibric acid Ciprofibratum [INN-Latin] Ciprofibrato [INN-Spanish] 2-(p-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropionicacid 2-(4-(2,2-Dichlorocyclopropyl)phenoxy)2-methylpropanoic acid 2-[4-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropionic acid 2-(p-(2,2-Dichlorocyclopropyl)phenoxy)-2-methylpropionic acid Propanoic acid, 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methyl- |
| CAS | 52214-84-3 |
| EINECS | 257-744-6 |
| InChI | InChI=1/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 |
Ciprofibric acid - Physico-chemical Properties
| Molecular Formula | C13H14Cl2O3 |
| Molar Mass | 289.15 |
| Density | 1.2576 (rough estimate) |
| Melting Point | 114-116° |
| Boling Point | 401.74°C (rough estimate) |
| Flash Point | 210.7°C |
| Solubility | Practically insoluble in water, freely soluble in anhydrous ethanol, soluble in toluene. |
| Vapor Presure | 5.63E-08mmHg at 25°C |
| Appearance | neat |
| Color | White to Pale Beige |
| Merck | 14,2313 |
| pKa | 3.31±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.5209 (estimate) |
| MDL | MFCD00467135 |
| Physical and Chemical Properties | A light cream colored solid was obtained from hexane, melting point 114-116 °c. |
| Use | It has hypolipidemic effect, stronger than the role of clofibrate. Can significantly reduce the level of very low density and low density lipoprotein, and increase the high density lipoprotein. By improving the distribution of cholesterol, the deposition of CH and LDL in the vessel wall can be reduced. There is also the effect of dissolving fibrin and preventing platelet aggregation. |
Ciprofibric acid - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | 45 - May cause cancer |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S22 - Do not breathe dust. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| WGK Germany | 3 |
| RTECS | UF0880000 |
| HS Code | 29189900 |
Ciprofibric acid - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Overview | Cyprofibrate (ciprofibrate) is a phenoxyacetic acid hypolipidemic drug, the chemical name is 2-[ 4-(2, 2-dichlorocyclopropyl) phenoxy]-2-methylpropionic acid, also known as chloropropramine, is the same as gemfibrozil and is a new type of lipid-lowering drug. It can competitively inhibit HMG-CoA reductase and reduce cholesterol synthesis; increase the number of low-density lipoprotein receptors on the surface of liver cells, and increase the clearance of low-density lipoprotein cholesterol by liver cells; increase the activity of protease and increase the clearance of very low-density lipoprotein; Reduce blood viscosity, anticoagulation, anti-platelet aggregation, increase the effect of plasmin, and improve microcirculation. It has a lipid-lowering effect on normal people, non-familial and familial hyperlipidemia, which can reduce plasma total cholesterol, triglycerides, low-density lipoprotein and apolipoprotein B, and high-density lipoprotein and apolipoprotein A1 It has an elevated effect, and can be used as the first-line lipid-lowering drug, and can also be used as an alternative drug when the treatment of other lipid-lowering drugs fails. The longer the course of treatment, the higher the original blood lipid level, the better the treatment effect. It can remove tendinous and vascular xanthoma on the blood vessel wall and reduce the risk factors of coronary heart disease. For patients with slightly increased blood lipids, this product should be selected when other drug treatments are not good. |
| pharmacological action | this product is similar to clofibrate, has a stronger hypolipidemic effect than fenofibrate, competitively inhibits HMG-CoA reductase, and reduces cholesterol synthesis; Increase the number of LDL receptors on the surface of liver cells to increase the ability of liver cells to remove LDL-C; Increase lipoprotein enzyme activity to increase the clearance rate of VLDL; Reduce blood viscosity, increase fibrinolytic enzyme activity and improve microcirculation. It can reduce low-density lipoprotein and very low-density lipoprotein, and increase high-density lipoprotein. In addition, there are anti-platelet aggregation and fibrin dissolving effects. |
| synthetic route | method 1: using cheap styrene as starting material, ketone compound 4 is formed after ring formation and Friedel-Crafts acylation, maleic anhydride, acetic anhydride and hydrogen peroxide with volume fraction of 30% are mixed to generate peroxyacid in situ, and then rearranged with compound 4 to generate phenolic ester (5) by Baeyer-Villiger, thus greatly improving the safety of operation. Since α-bromoisobutyrate is more expensive, in order to reduce the synthesis cost, compound 6 is reacted with acetone and chloroform under alkaline conditions to undergo a Bargellini reaction to obtain cyprofibrate. The specific reaction process is as follows: Method 2: p-hydroxybenzaldehyde (I) and malonic acid undergo condensation and decarboxylation reaction under alkaline catalyst, the reaction of p-hydroxystyrene (II) and p-hydroxystyrene (II) with 2-haloisobutyrate under the action of alkali to obtain etherification product (III), etherification product (III) and chloroform under alkaline conditions, cyclization reaction occurs under the action of phase transfer catalyst to obtain cyclization product (IV), cyclization product (IV) in alkali solution alcoholysis and acidification, cyclopropfibrate (V) is obtained by recrystallization; the method of the present invention has short synthesis steps, simple and convenient industrial operation, mild conditions and easy control, almost no possibility of accidents such as explosion, safe operation, convenient post-processing, stable process, and easy Large-scale industrial production, and only conventional acid and alkali and solvents are used in the entire reaction process, the cost is low, the environment is friendly, and the yield is increased by more than 15%. The specific reaction process is as follows: method 3: using p-hydroxystyrene as raw material, cyprofibrate was prepared by Bargellini and ring forming reaction in two steps. Compared with the traditional method, this method has the advantages of fewer reaction steps, short production cycle, simple operation, mild and easy control conditions, convenient post-treatment, environmental friendliness and higher total yield. It is a brand-new industrial synthesis of cyprofibrate. The specific reaction process is as follows: |
| pharmacokinetics | oral absorption is good, reaching a peak value in 2 hours. T1/2 is 17h. It is mainly excreted by the kidney, and those with normal renal function have no accumulation after taking it for a long time. |
| indications | for the treatment of adult endogenous hypercholesterolemia and hypertriglyceridemia, can be used alone or in combination with other drugs. The effect is more obvious for patients with poor effect of diet therapy, high blood cholesterol level or risk of complications. |
| specification | capsule: 100mg. |
| usage and dosage | adults, 100mg each time, once a day. In patients with moderate renal impairment, 100mg each time, the drug is administered every other day. |
| adverse reactions | adverse reactions are less. long-term application may include loss of appetite, nausea, stomach discomfort, headache, dizziness, dizziness, fatigue, skin reaction, alopecia, impotence, anemia, leukopenia, muscle toxicity and thrombocytopenia. |
| drug interaction | 1. combination with anticoagulant drugs can enhance anticoagulant effect. 1/3 dose of anticoagulant should be reduced and prothrombin should be checked. 2. The combination of hepatotoxic drugs such as piecxilin and monoamine oxidase inhibitors can increase or aggravate hepatotoxicity and should not be combined. 3. It can be used in combination with niacin derivatives and cholesterol-lowering resins, and can be used in combination with colai tepoise to increase curative effect and reduce side effects |
| precautions | 1. patients with renal function injury should be used with caution. 2. If there is suspicious muscle toxicity or creatine phosphokinase concentration is significantly increased, stop the drug. 3. For patients with slightly elevated blood lipids, you can first use drugs with mild effects and small side effects. This medicine is used when the effect is not good. 4. Check liver function before medication, and then recheck once every 2 weeks. If transaminase is found to be elevated, stop medication immediately. |
| taboo | patients with severe liver and kidney function injury, hypoalbuminemia, primary biliary cirrhosis and gallbladder disease are contraindicated. |
| medication for pregnant and lactating women | pregnant and lactating women are prohibited. |
| children's medication | the safety of children's long-term medication has not been determined, and is limited to children with severe lipid metabolism disorders and obvious curative effect on this product. |
| Main reference materials | [1] Editor-in-Chief Zhang Qingxian. Handbook of Refined New Drugs for Common Use. Zhengzhou: Henan Science and Technology Press. 2009. No. 228-2. [2] Editor-in-Chief Xu Yuanzhen. New all-practical drug manual. Zhengzhou: Henan Science and Technology Press. 2005. Page 598. [3] Any editor-in-chief. Family doctor encyclopedia. Wuhan: Chongwen Bookstore. 2001. Page 64-67. [4] Editor-in-Chief Chen Jisheng. New clinical pharmacology. Beijing: China Traditional Chinese Medicine Press. 2013. [5] Li Jingfeng et al. Synthesis of cyprofibrate. Journal of Shenyang Pharmaceutical University. 2008,25(12):954-955. [6] yuan weicheng et al.. a new method for synthesizing cyprofibrate. application number CN201510711121.1. application date 2015-10-28. [7] Wang xun et al.. a green preparation method for a hypolipidemic drug cyprofibrate. application number CN201310237441.9. application date 2013-06-14. [8] practical drug manual. Jinan: Shandong Science and Technology Press. 1999. Page 711. |
| uses | hypolipidemic drugs, as well as anti-platelet aggregation and fibrinolytic effects. When the effect of diet therapy is not obvious, especially when the blood cholesterol is still high or there is a risk of complications, use alone or in combination with other drugs to treat adult endogenous hypercholesterolemia and hypertriglyceridemia. |
| Production method | 8g(0.0356 mo1)4-(2,2-dichlorocyclopropyl) phenol, 11.2g(0.28mol) solid sodium hydroxide, 11g chloroform and 350ml acetone were mixed at 0°C. Remove the cold bath, stir for a while, and then heat on the steam bath until reflux. After stirring and reflux for 3h, vacuum concentration. The remaining liquid is distributed with dilute sodium bicarbonate aqueous solution and ether. Sodium bicarbonate solution was extracted with ether after acidification with concentrated hydrochloric acid. The extract is dried with anhydrous sodium sulfate and concentrated. The yellow oily remaining liquid (9.5g) was recrystallized twice with hexane to obtain 6.0g of light cream-colored cyprofibrate solid with a melting point of 114-116 ℃. |
Last Update：2024-04-10 22:29:15
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