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S6196

Sigma-Aldrich

Simvastatin

≥97% (HPLC), solid

Synonym(s):

MK-733, SVA

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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

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.

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 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 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.

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.

Pictograms

Health hazard

Signal Word

Warning

Hazard 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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MYC-regulated mevalonate metabolism maintains brain tumor-initiating cells
Wang X, et al.
Cancer research, 77(18), 4947-4960 (2017)
Statins and Cardiovascular Diseases: From Cholesterol Lowering to Pleiotropy
Zhou Q, et al.
Current Pharmaceutical Design, 15(5), 467-467 (2009)
Statins may have double-edged effects in patients with lung adenocarcinoma after lung resection
Nishikawa S, et al.
Cancer Management and Research, 11, 3419-3419 (2019)
Simvastatin
Analytical profiles of drug substances and excipients, 22, 359-388 (1993)
Veluchamy A Barathi et al.
Investigative ophthalmology & visual science, 55(1), 460-468 (2014-01-09)
To determine the effect of a statin (simvastatin) on the ultrastructure and function of the RPE, Bruch's membrane (BM), and photoreceptor interface in a high-fat atherogenic mouse model of thickened BM. Wild-type C57BL/6 mice (6-weeks old) were divided into three

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