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S6196 Sigma-Aldrich

Simvastatin

≥97% (HPLC), solid

  • CAS Number 79902-63-9

  • Empirical Formula (Hill Notation) C25H38O5

  • Molecular Weight 418.57

  •  MDL number MFCD00072007

  •  PubChem Substance ID 24724617

  •  NACRES NA.77

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Arachidonic Acid Cascade, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cancer Metabolism,
Quality Level   100
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)

Description

General description

Simvastatin is a prodrug. Simvastatin is a semisynthetic derivative 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

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.

Packaging

25 mg in poly bottle

5 mg in glass bottle

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 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, 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 may also have beneficial effects on endothelial function, inflammation, smooth muscle cell function, vascular wall function, 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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
EK7798000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

Please Enter a Lot Number

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 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.
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 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?
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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Protocols & Articles

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Peer-Reviewed Papers
15

References

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