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38956

Supelco

Simvastatin

analytical standard

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About This Item

Empirical Formula (Hill Notation):
C25H38O5
CAS Number:
79902-63-9
Molecular Weight:
418.57
MDL number:
MFCD00072007
UNSPSC Code:
41116107
PubChem Substance ID:
329755810
NACRES:
NA.24

grade

analytical standard

Quality Level

100

Assay

≥98.0% (HPLC)

optical activity

[α]/D +275±25°, c = 1 in acetonitrile

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

impurities

≤0.5% water

mp

127-132 °C (lit.)

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

format

neat

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)

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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).

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK8867
BCCG4003
BCCC8162
BCCB9688
BCCB7519

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Peter J Kirkpatrick et al.
The Lancet. Neurology, 13(7), 666-675 (2014-05-20)
The benefit of statins in patients with acute aneurysmal subarachnoid haemorrhage is unclear. We aimed to determine whether simvastatin 40 mg could improve the long-term outcome in patients with this disorder. In this international, multicentre, randomised, double-blind trial, we enrolled
Joost Besseling et al.
JAMA, 313(10), 1029-1036 (2015-03-11)
Familial hypercholesterolemia is characterized by impaired uptake of cholesterol in peripheral tissues, including the liver and the pancreas. In contrast, statins increase the cellular cholesterol uptake and are associated with increased risk for type 2 diabetes mellitus. We hypothesize that
Anders M Greve et al.
Stroke, 45(7), 1939-1946 (2014-06-07)
There are limited data on risk stratification of stroke in aortic stenosis. This study examined predictors of stroke in aortic stenosis, the prognostic implications of stroke, and how aortic valve replacement (AVR) with or without concomitant coronary artery bypass grafting
A Marot et al.
Acta clinica Belgica, 66(2), 134-136 (2011-06-03)
Myopathy, including rhabdomyolysis, is a well-known, albeit rare complication of statin therapy. Predisposing factors include comorbidities and the concomitant use of cytochrome P-450 (CYP) 3A4 inhibitors. We report a case of severe simvastatin-induced rhabdomyolysis triggered by the addition of amiodarone
Laura Marin et al.
Expert opinion on drug delivery, 8(9), 1205-1220 (2011-05-28)
Chronic Obstructive Pulmonary Disease (COPD) is a severe disease that leads to a non-reversible obstruction of the small airways. The prevalence of this disease is rapidly increasing in developed countries, and in 2020 it has been predicted that this disease
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