93957-55-2 Usage
Uses
Used in Pharmaceutical Industry:
Fluvastatin sodium salt is used as a pharmaceutical secondary standard for application in quality control, providing pharmaceutical laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Used in Cardiovascular Health:
Fluvastatin sodium salt is used as an HMG-CoA reductase inhibitor for lowering total and low-density lipoprotein (LDL) cholesterol levels, helping to prevent cardiovascular diseases.
Used in Anti-hyperlipoproteinemia:
Fluvastatin sodium salt is used as an anti-hyperlipoproteinemic agent, specifically as an antilipemic, to manage and treat conditions related to high levels of lipids in the blood.
Used in Research and Development:
Fluvastatin-d6 Sodium Salt, the labeled analogue of Fluvastatin Sodium Salt, is used in research and development for studying the effects and mechanisms of HMG-CoA reductase inhibitors in various biological and medical applications.
Commonly used cholesterol-lowering drugs
Fluvastatin sodium salt is commonly used as a cholesterol-lowering drug, cholesterol-lowering effect is very good, the trade name of the commercially available products is Lescol,which is produced by Novartis. Fluvastatin sodium salt is a fully synthetic cholesterol-lowering drug, it belongs to methylglutaryl coenzyme A (HMC-CoA) reductase inhibitors, the main function is performed in the liver ,it can transform HMG-CoA into 3-methyl-3,5-dihydroxy acid, it can inhibit the synthesis of endogenous cholesterol ,and reduce cholesterol content in liver cells, it can stimulate the synthesis of low density lipoprotein (LDL) receptors,and enhance the uptake of LDL particles, reduce the plasma total cholesterol concentration.it can significantly reduce total cholesterol, LDL cholesterol, triglycerides, and increase high-density lipoprotein cholesterol.
The above information is edited by the lookchem of Tian Ye.
production method
1. After condensation of (chloroacetyl) fluorobenzeneand N-isopropyl aniline , the compound (I) is obtained. Then in acetonitrile, under the presence of phosphorus oxychloride, react with N, N-dimethylamino acrolein , the compound (Ⅱ) is obtained. Compound (Ⅱ) in the role of a strong base, after condensation with methyl acetoacetate , and then splitting ,the compound (Ⅲ) is produced. At-77 ~-74 ℃, the compound (Ⅲ) is added dropwise into a mixture of boron sodium borohydride , methanol, tetrahydrofuran and diethyl methoxy ,stir 30min; cyclic boronic ester obtained in ethyl acetate is treated with 30% hydrogen peroxide; then it is hydrolyzed to obtain fluvastatin sodium.
2. the compound (Ⅳ)is obtained by catalytic hydrogenation of Phloroglucinol . React it With tert-butyldiphenylsilyl chloride to produce the compound (V), and then oxidize it to generate (Ⅵ). After oxidation of chloroperbenzoic acid to obtain (Ⅶ), (Ⅷ) is produced through ring-opening . And then it is oxidized to (IX) . (Ⅺ) is obtained through condensation of (Ⅸ) and intermediate x , after deprotection and hydrolysis, obtain fluvastatin sodium.
Intermediate (X) can be made through starting from the compound (I), via formylation, reduction, chlorination, and then reacting with triphenylphosphine .
Originator
Sandoz (Switzerland)
Therapeutic Function
Antihyperlipidemic
Biological Activity
Orally active, potent and competitive HMG-CoA reductase inhibitor (IC 50 = 40 -100 nM at human liver microsomes). Inhibits vascular smooth muscle proliferation in vitro (IC 50 = 70 nM) and exhibits antihypercholesterolemic and antioxidant activity in vivo .
Biochem/physiol Actions
Fluvastatin is a competitive inhibitor of hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase, the enzyme that catalyzes the conversion of HMG-CoA to mevalonic acid, the rate-limiting step in cholesterol biosynthesis. Fluvastatin is antilipemic and is used to reduce plasma cholesterol levels and prevent cardiovascular disease.
References
1) Dansette?et al. (2000),?HMG-CoA reductase activity in human liver microsomes: comparative inhibition by statins; Exp. Toxicol. Pathol.,?52?145
2) Turner?et al.?(2007),?Comparison of the efficacies of five different statins on inhibition of human saphenous vein smooth muscle cell proliferation and invasion: J. Cardiovasc. Pharmacol.,?50?458
3) McFarland?et al.?(2017),?Statins Reduce Lipopolysaccharide-Induced Cytokine and Inflammatory Mediator Release in an In Vitro Model of Microglial-like Cells; Mediators Inflamm.,?2582745
4) Yang?et al.?(2017),?Fluvastatin Prevents Lung Adenocarcinoma Bone Metastasis by Triggering Autophagy; EBioMedicine,?19?49
5)Higashi?et al.?(2016),?Statin attenuates cell proliferative ability via TAZ (WWTR1) in hepatocellular carcinoma; Med. Oncol.,?33?123
Check Digit Verification of cas no
The CAS Registry Mumber 93957-55-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,3,9,5 and 7 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 93957-55:
(7*9)+(6*3)+(5*9)+(4*5)+(3*7)+(2*5)+(1*5)=182
182 % 10 = 2
So 93957-55-2 is a valid CAS Registry Number.
InChI:InChI=1/C24H26FNO4.Na/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30;/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30);/q;+1/p-1/b12-11+;/t18-,19-;/m1./s1
