Simvastatin is a prodrug. Simvastatin is a semisynthetic derivative/analog of lovastatin. Simvastatin is insoluble in water but is soluble in polar organic solvents.
Application
Simvastatin has been used:
as an inhibitor of HMG CoA reductase (HMGCR)
to study its effects on epithelial to mesenchymal transition (EMT) and the prognosis of patients with lung adenocarcinoma
in in vivo studies to test its effect on brain tumor−initiating cells (BTIC) viability and cell proliferation
to study the role of adenosine triphosphate (ATP)-binding cassette transporter A7 in phagocytosis of Jurkat cells
to study the effect on endothelial dysfunction and inflammation in mice
Biochem/physiol Actions
Simvastatin is a specific inhibitor of HMG-CoA reductase, the enzyme that catalyzes the conversion of HMG-CoA to mevalonate, an early step in cholesterol biosynthesis. It is used in the treatment of hypercholesterolemia, as it reduces levels of low-density lipoproteins cholesterol and triglycerides, and raises high-density lipoprotein levels. Simvastatin is a lactone that is readily hydrolyzed in vivo to the corresponding β-hydroxyacid and can be activated prior to use with NaOH in EtOH treatment. It may also have beneficial effects on endothelial function, inflammation, smooth muscle cell function, vascular wall function, hemostasis and LDL oxidation.
Simvastatin is a specific inhibitor of HMG-CoA reductase and cholesterol lowering drug.
Simvastatin is a specific inhibitor of HMG-CoA reductase, the enzyme that catalyzes the conversion of HMG-CoA to mevalonate, an early step in cholesterol biosynthesis. It is used in the treatment of hypercholesterolemia, as it reduces levels of low-density lipoproteins and triglycerides, and raises high-density lipoprotein levels. Simvastatin is a lactone that is readily hydrolyzed in vivo to the corresponding β-hydroxyacid, and can be activated prior to use with NaOH in EtOH treatment. It is a synthetic analog of lovastatin (Cat. No. M2147).
This item has not been tested for use in cell culture. However, the product has been used successfully for in vitro and in vivo applications by other researchers. Please see the links below to review example publications: MYC-regulated mevalonate metabolism maintains brain tumor-initiating cells https://pmc.ncbi.nlm.nih.gov/articles/PMC5600855/
Effects of simvastatin on retinal structure and function of a high-fat atherogenic mouse model of thickened Bruch's membrane. https://pubmed.ncbi.nlm.nih.gov/24398101/
Helpful?
·a year ago
How can S6196 be stored for long term storage after DMSO resuspension?
1 answer
Technical Support
·a year ago
The solubility of this material has not been tested in DMSO. However, external sources report that Simvastatin is soluble in DMSO at >50 mg/mL. Stock solutions may be stored in DMSO at -20°C for at least 1 month. This information has not been validated. As a general rule, avoid repeated freeze/thaw cycles.
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·2 years ago
What happens when the drug is not activated before use in in vitro experiments?
1 answer
Technical Support
·2 years ago
This material does not require activation for cell-based in vitro studies, as it is readily hydrolyzed by the cells. For experiments without live cells the product will remain inactive. This material may be chemically activated per M. Sadeghi et al., J. Immunol., 165, 2712-2718 (2000) as noted below: 1. 4 mg of simvastatin is dissolved in 100 μl of ethanol. 2. Then 150 μl of 0.1 N NaOH was added to the solution and subsequently incubated at 50 °C for 2 hours. 3. The pH was brought to 7.0 by HCl, and the final concentration of the stock solution was adjusted to 4 mg/ml. The stock solution was kept at 4 °C.
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Anonymous
·4 years ago
What is the Department of Transportation shipping information for this product?
1 answer
Technical Support
·4 years ago
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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Anonymous
·4 years ago
What is the solution stability of Product S6196, Simvastatin, in various solvents?
1 answer
Technical Support
·4 years ago
Sigma-Aldrich has not determined the solution stability of simvastatin. One publication on the subject, published by Yang, H. et al., reports that a 50 mg/mL stock solution of simvastatin in methanol was stored for one month at 4°C. Reference: Determination of Simvastatin in human plasma by liquid chromatography-mass spectrometry. J. Chromatography B, 785(2), 369-375 (2003).
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Anonymous
·4 years ago
How is Product S6196, Simvastatin, activated?
1 answer
Technical Support
·4 years ago
An activation procedure from M. Sadeghi, et al., J. Immunol., 165, 2712-2718 (2000) is:1. 4 mg of simvastatin is dissolved in 100 μl of ethanol.2. Then 150 μl of 0.1 N NaOH was added to the solution and subsequently incubated at 50 °C for 2 hours.3. The pH was brought to 7.0 by HCl, and the final concentration of the stock solution was adjusted to 4 mg/ml. The stock solution was kept at 4 °C.
Helpful?
Anonymous
·4 years ago
What is Product S6196, Simvastatin, soluble in?
1 answer
Technical Support
·4 years ago
According to the chemicals encyclopedia published by the Royal Society of Chemistry, 14th ed., Entry # 8539, simvastatin is soluble in chloroform at 610 mg/mL, DMSO at 540 mg/mL, methanol at 200 mg/mL, ethanol at 160 mg/mL, 0.1 M HCl at 60 μg/mL, PEG-400 at 70 mg/mL, 0.1 M NaOH at 70 mg/mL, and water at 30 μg/mL. Please note that some of the values are given in milligrams per mL and others are in micrograms per mL.
