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Merck

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
Quality level:
100

Key Documents

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Product Name

Simvastatin, ≥97% (HPLC), solid

form

solid

color

white

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 key

RYMZZMVNJRMUDD-HGQWONQESA-N

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

assay

≥97% (HPLC)

mp

127-132 °C (lit.)

solubility

DMSO: ≥20 mg/mL

originator

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

storage temp.

2-8°C

Quality Level

100

Gene Information

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

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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 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).
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.

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.

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)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

S6196-VAR: + S6196-5MG: + S6196-25MG: + S6196-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
116M4716V
026M4727V
044M4713V
113M4764V
053M4728V

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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)
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)
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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