93957-55-2 Usage
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.
Chemical Properties
Different sources of media describe the Chemical Properties of 93957-55-2 differently. You can refer to the following data:
1. Melting point 194~197 ℃.
2. Yellow Powder
Uses
Different sources of media describe the Uses of 93957-55-2 differently. You can refer to the following data:
1. HMG-CoA reductase inhibitors.
2. Anti- hyperlipoproteinemic;'HMG CoA reductase inhibitor
3. Fluvastatin-d6 Sodium Salt is the labeled analogue of Fluvastatin Sodium Salt (F601250), a synthetic HMG-CoA reductase inhibitor. Antilipemic.
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 .
Description
Fluvastatin sodium is the fourth HMG-CoA reductase inhibitor to reach the market
as a dietary adjunct for lowing total and low-density lipoprotein (LDL) cholesterol.
Fluvastatin sodium is the first totally synthetic inhibitor of its class and has more
potent effects on reducing serum total and LDL cholesterol and serum triglyceride
levels than compactin or lovastatin. Moreover, fluvastatin exhibits a unique set of
pharmacological properties including a biopharmaceutical profile most consistent
with hepatoselectivity. It has been reported to be well tolerated and to exhibit a
safety profile superior to other agents of its class. The main mechanism by which
HMG-CoA reductase inhibitors lower plasma cholesterol has been suggested to be
up-regulation of hepatocellular LDL-receptor expression and enhancement of
receptor-mediated clearance and catabolism of LDL cholesterol.
Originator
Sandoz (Switzerland)
Therapeutic Function
Antihyperlipidemic
General Description
Fluvastatin sodium is a lipid-lowering drug that belongs to the group of compounds known as statins. It acts by inhibiting the enzyme HMG-CoA reductase that plays a key role in the cholesterol production. It is generally used to reduce plasma cholesterol levels and prevent cardiovascular disease.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
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
