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.
S6196
Simvastatin
≥97% (HPLC), solid
Synonym(s):
MK-733, SVA
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5 MG
$62.30
25 MG
$249.00
About This Item
Empirical Formula (Hill Notation):
C25H38O5
CAS Number:
Molecular Weight:
418.57
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
Assay
≥97% (HPLC)
form
solid
color
white
mp
127-132 °C (lit.)
solubility
DMSO: ≥20 mg/mL
originator
Merck & Co., Inc., Kenilworth, NJ, U.S.
storage temp.
2-8°C
SMILES string
[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]3C[C@@H](O)CC(=O)O3)OC(=O)C(C)(C)CC
InChI
1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
InChI key
RYMZZMVNJRMUDD-HGQWONQESA-N
Gene Information
human ... HMGCR(3156)
rat ... Hmgcr(25675)
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General description
Simvastatin is a prodrug. Simvastatin is a semisynthetic derivative/analog of lovastatin. Simvastatin is insoluble in water but is soluble in polar organic solvents.[1]
Application
Simvastatin has been used:
- as an inhibitor of HMG CoA reductase (HMGCR)[2]
- to study its effects on epithelial to mesenchymal transition (EMT) and the prognosis of patients with lung adenocarcinoma[3]
- in in vivo studies to test its effect on brain tumor−initiating cells (BTIC) viability and cell proliferation[4]
- 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 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).
Simvastatin is a specific inhibitor of HMG-CoA reductase,[2] 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,[1] 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,[5] hemostasis and LDL oxidation.
Features and Benefits
This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Repr. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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What happens when the drug is not activated before use in in vitro experiments?
1 answer-
Helpful?
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What is Product S6196, Simvastatin, soluble in?
1 answer-
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.
Helpful?
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What is the solution stability of Product S6196, Simvastatin, in various solvents?
1 answer-
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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What is the Department of Transportation shipping information for this product?
1 answer-
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.
Helpful?
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How is Product S6196, Simvastatin, activated?
1 answer-
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.
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