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Chemistry of simvastatin? 


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Simvastatin is a cholesterol-lowering drug used in the treatment of cardiovascular diseases related to high cholesterol levels. It is derived from lovastatin, a secondary metabolite of fungal origin . Simvastatin inhibits the enzyme 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMGR), which is involved in cholesterol biosynthesis . It effectively lowers plasma cholesterol levels and has been reported to have therapeutic applications in regulating inflammatory and immune responses, bone turnover, neovascularization, vascular tone, and arterial pressure . Various methods have been developed for the production of simvastatin, including chemical synthesis, enzymatic synthesis, and biological synthesis . Analytical methods, such as reverse phase high-performance liquid chromatography (RP-HPLC), have been developed for the accurate and precise estimation of simvastatin and its impurities . The synthesis of simvastatin involves several steps, including the protection and deprotection of functional groups, methylation, and ring closure .

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Papers (5)Insight
Patent
Hongjie Liu, Xiongyan Zhao, Mingzhu Wang 
23 May 2012
3 Citations
The paper provides a method for preparing simvastatin, but it does not provide detailed information about the chemistry of simvastatin.
The paper does not provide information about the chemistry of simvastatin.
The paper does not provide information about the chemistry of simvastatin.
Patent
Li Youxiang, Sun Jun 
19 Feb 2014
2 Citations
The paper does not provide information about the chemistry of simvastatin.
The paper provides an overview of various chemical and biological methods used for the production of simvastatin, a cholesterol-lowering drug. It discusses the use of lovastatin as a starting material and highlights enzymatic synthesis of simvastatin.

Related Questions

How to conduct HPLC-uv analyses for lovastatin?5 answersTo conduct HPLC-UV analyses for lovastatin, a suitable method involves using a reverse-phase HPLC system with specific parameters. The method typically includes a C18 column, an isocratic elution system with a mobile phase consisting of a mixture of acetonitrile and phosphate buffer, and UV detection at a specific wavelength. The flow rate, column temperature, and injection volume are crucial parameters to consider for accurate analysis. Lovastatin elutes at a specific retention time, which aids in its identification and quantification. The method should be validated following regulatory guidelines to ensure accuracy, precision, and reproducibility. By adhering to these parameters and validation criteria, a reliable HPLC-UV method can be established for the analysis of lovastatin in various samples.
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How to prepare simvastatin drugs for cell culture?5 answersSimvastatin drugs for cell culture can be prepared using various methods. One method involves micronizing simvastatin to improve its particle diameter and specific surface area, which facilitates increased in vitro dissolution rate and uniformity of dissolution rate of the simvastatin tablets. Another method involves preparing a solid dispersion of simvastatin using spray-drying technology, which results in simvastatin tablets with a slow quick-release feature in in-vitro dissolution, closer to an S-shaped dissolution curve, and higher stability. A different method involves subjecting simvastatin ammonium salt to cyclization, decoloring, and concentration to obtain a crude simvastatin product, which is then refined to obtain medical simvastatin with improved product yield, reduced impurities, and enhanced quality. Additionally, highly pure simvastatin can be prepared economically by treating lovastatin with potassium hydroxide, relactonizing the resulting compound, and acylating it with 2,2-dimethylbutyryl chloride or 2,2-dimethylbutyryl bromide.
Physical properties of simvastatin?5 answersSimvastatin is a drug used to reduce high cholesterol levels. It exists in both lactone and dihydroxyheptanoate forms, with the latter being the active form in the liver. Simvastatin can be prepared in amorphous forms using cryo-milling or melting and quench-cooling methods. These amorphous forms have different physicochemical properties and stability, with the cryo-milled form showing faster recrystallization compared to the quench-cooled form. Simvastatin can also be combined with other compounds, such as ezetimibe, to improve its physical stability. The binary amorphous ezetimibe-simvastatin system is physically stable for at least 1 year at room temperature. Simvastatin can incorporate into lipid bilayers and affect their properties, increasing membrane order in pure bilayers and membrane fluidity in bilayers containing cholesterol. Simvastatin has various pharmacological properties, including inhibiting cholesterol synthesis, regulating inflammatory and immune response, and affecting bone turnover and vascular tone. A solid medicine composition of simvastatin has been developed, which includes simvastatin, citric acid, BHA, stearic acid, and other excipients.

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