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Merck

S6196

Simvastatin

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

Sinónimos:

MK-733, SVA

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Fórmula empírica (notación de Hill):
C25H38O5
Número CAS:
Peso molecular:
418.57
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Assay:
≥97% (HPLC)
Form:
solid
Quality level:
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Nombre del producto

Simvastatin, ≥97% (HPLC), solid

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)

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 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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pictograms

Health hazard

signalword

Warning

hcodes

Hazard Classifications

Repr. 2

Clase de almacenamiento

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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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)
MYC-regulated mevalonate metabolism maintains brain tumor-initiating cells
Wang X, et al.
Cancer research, 77(18), 4947-4960 (2017)