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Merck

S6196

Sigma-Aldrich

Simvastatin

≥97% (HPLC), solid

Sinónimos:

MK-733, SVA

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About This Item

Fórmula empírica (notación de Hill):
C25H38O5
Número de CAS:
Peso molecular:
418.57
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

Análisis

≥97% (HPLC)

formulario

solid

color

white

mp

127-132 °C (lit.)

solubilidad

DMSO: ≥20 mg/mL

emisor

Merck & Co., Inc., Kenilworth, NJ, U.S.

temp. de almacenamiento

2-8°C

cadena SMILES

[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

Clave InChI

RYMZZMVNJRMUDD-HGQWONQESA-N

Información sobre el gen

human ... HMGCR(3156)
rat ... Hmgcr(25675)

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Descripción general

Simvastatin is a prodrug. Simvastatin is a semisynthetic derivative/analog of lovastatin. Simvastatin is insoluble in water but is soluble in polar organic solvents.

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Características y beneficios

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.

Pictogramas

Health hazard

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Repr. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Nishikawa S, et al.
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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)
MYC-regulated mevalonate metabolism maintains brain tumor-initiating cells
Wang X, et al.
Cancer research, 77(18), 4947-4960 (2017)
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Analytical profiles of drug substances and excipients, 22, 359-388 (1993)
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Investigative ophthalmology & visual science, 55(1), 460-468 (2014-01-09)
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Artículos

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Randomized controlled clinical studies have suggested 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors (statins) are effective in both primary and secondary prevention of cardiovascular disease (CVD) events.

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