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S6196 Sigma

Simvastatin

≥97% (HPLC), solid

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Arachidonic Acid Cascade, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cancer Metabolism,
InChI Key   RYMZZMVNJRMUDD-HGQWONQESA-N
assay   ≥97% (HPLC)
form   solid
color   white
mp   127-132 °C(lit.)
solubility   DMSO: ≥20 mg/mL
originator   Merck & Co., Inc., Kenilworth, NJ
storage temp.   2-8°C
Gene Information   human ... HMGCR(3156)
rat ... Hmgcr(25675)

Description

Biochem/physiol Actions

Simvastatin, a synthetic analog of lovastatin, is a specific inhibitor of HMG-CoA reductase (3-hydroxy-3-methyl-glutaryl-CoA reductase.) HMG-CoA is a major therapeutic target for reduction of low density lipoprotein (LDL) cholesterol. Simvastatin may also have beneficial effects on endothelial function, smooth muscle cell function, hemostasis, vascular wall function, LDL oxidation, and inflammation. Simvastatin can be activated prior to use by treatment with NaOH in EtOH.

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).

Packaging

25 mg in poly bottle

5 mg in glass bottle

Application

Simvastatin was used to study the role of ATP-binding cassette transporter A7 in phagocytosis of Jurkat cells. Mice were treated with simvastatin to study the effect on endothelial dysfunction and inflammation.

Features and Benefits

This compound was developed by Merck & Co., Inc., Kenilworth, NJ. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
2
RTECS 
EK7798000

Documents

Certificate of Analysis

Certificate of Origin

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
What isProduct S6196, Simvastatin, soluble in?
According to the Merck Index, 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.
How isProduct S6196, Simvastatin, activated?
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.
What is the solution stability ofProduct S6196, Simvastatin, in various solvents?
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 chromatographymass spectrometry.J. Chromatography B, 785(2), 369-375 (2003).
How do I find price and availability?
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What is the Department of Transportation shipping information for this product?
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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References

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