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S6196

Simvastatin

≥97% (HPLC),  HMG-CoA reductase inhibitor, solid

Synonym(s):

MK-733, SVA

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About This Item

Empirical Formula (Hill Notation):
C25H38O5
CAS Number:
79902-63-9
Molecular Weight:
418.57
UNSPSC Code:
12352200
PubChem Substance ID:
24724617
NACRES:
NA.77
MDL number:
MFCD00072007
Assay:
≥97% (HPLC)
Form:
solid
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Product Name

Simvastatin, ≥97% (HPLC), solid

Quality Segment

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)

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.

Application

Simvastatin has been used:
  • as an inhibitor of HMG CoA reductase (HMGCR)[1]
  • 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,[1] 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).

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.

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This Item
S065000056702038956
Simvastatin ≥97% (HPLC), solid

Sigma-Aldrich

S6196

Simvastatin

Simvastatin European Pharmacopoeia (EP) Reference Standard

S0650000

Simvastatin

Simvastatin A lipophilic 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitor that blocks Ras function through inhibition of farnesylation.

Sigma-Aldrich

567020

Simvastatin

Simvastatin analytical standard

Supelco

38956

Simvastatin

form

solid

form

-

form

solid

form

-

assay

≥97% (HPLC)

assay

-

assay

≥98% (HPLC)

assay

≥98.0% (HPLC)

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: ≥20 mg/mL

solubility

-

solubility

soluble (DMSO or Ethanol (50 mg/ml). Dissolve 50 mg in 1 ml in ethanol and add 0.813 ml of 1N NaOH. Adjust the pH to 7.2 by adding small quantities of 1N HCl before use.)

solubility

-

color

white

color

-

color

off-white

color

-

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pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Questions

1–7 of 7 Questions  

  1. Can S6196 be used for cell culture assays?

    1 answer

    1. 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?

  2. How can S6196 be stored for long term storage after DMSO resuspension?

    1 answer

    1. 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.

      Helpful?

  3. What happens when the drug is not activated before use in in vitro experiments?

    1 answer

    1. 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.

      Helpful?

  4. What is the solution stability of Product S6196, Simvastatin, in various solvents?

    1 answer

    1. 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).

      Helpful?

  5. What is the Department of Transportation shipping information for this product?

    1 answer

    1. 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?

  6. What is Product S6196, Simvastatin, soluble in?

    1 answer

    1. 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?

  7. How is Product S6196, Simvastatin, activated?

    1 answer

    1. 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?

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