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Merck

567020

Simvastatin

≥98% (HPLC), solid, HMG-CoA reductase inhibitor, Calbiochem®

Synonyme(s) :

Simvastatin, MK-733, L-Type Calcium Channel Blocker VI

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A propos de cet article

Formule empirique (notation de Hill) :
C25H38O5
Numéro CAS:
79902-63-9
Poids moléculaire :
418.57
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00072007
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze

Principaux documents

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Nom du produit

Simvastatin, A lipophilic 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitor that blocks Ras function through inhibition of farnesylation.

SMILES string

O1[C@@H](C[C@H](CC1=O)O)CC[C@@H]2[C@H]3[C@H](C[C@H](C=C3C=C[C@@H]2C)C)OC(=O)C(CC)(C)C

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

description

Merck USA index - 14, 8539

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

off-white

solubility

soluble (DMSO or Ethanol (50 mg/ml). Dissolve 50 mg in 1 ml in ethanol and add 0.813 ml of 1N NaOH. Adjust the pH to 7.2 by adding small quantities of 1N HCl before use.)

cation traces

heavy metals: ≤20 ppm, heavy metals: <20 ppm

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Catégories apparentées

Disclaimer

Toxicity: Standard Handling (A)

Biochem/physiol Actions

Cell permeable: no
Primary Target
farnesylation
Product does not compete with ATP.
Reversible: no

General description

A lipophilic 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitor that blocks Ras function through inhibition of farnesylation. Also inhibits glucose-induced Ca2+-signaling and insulin secretion by blocking L-type Ca2+ channels in rat islet β-cells. Inhibits cell proliferation of human smooth muscle cells. Note: This product is supplied in an inactive form and requires treatment with NaOH in ethanol followed by neutralization to pH 7.2 for activation.

Other Notes

Yada, T., et al. 1999. Br. J. Pharmacol. 126, 1205.
Clutterbuck, R.D., et al. 1998. Br. J. Haematol. 102, 522.
Yokoyama, K., et al. 1998. Mol. Biochem. Parasitol. 94, 87.
Negre-Aminou, P., et al. 1997. Biochim. Biophys. Acta 1345, 259.
Vrtovsnik, F., et al. 1997. Kidney Int. 52, 1016.
Keyomarsi, K., et al. 1991. Cancer Res.51, 3602.

Preparation Note

Dissolve 50 mg in 1 ml in ethanol and add 0.813 ml of 1N NaOH. Adjust the pH to 7.2 by adding small quantities of 1N HCl before use.
Following reconstitution in ethanol-NaOH, aliquot and freeze (-20°C) Ethanol-NaOH solutions are stable for up to 1 month at -20°C. Neutralized solutions should be used immediately.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificats d'analyse (COA)

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Angela Jeong et al.
ACS chemical biology, 17(10), 2863-2876 (2022-09-16)
Dysregulation of protein prenylation has been implicated in many diseases, including Alzheimer's disease (AD). Prenylomic analysis, the combination of metabolic incorporation of an isoprenoid analogue (C15AlkOPP) into prenylated proteins with a bottom-up proteomic analysis, has allowed the identification of prenylated
Lívia Teixeira et al.
Frontiers in immunology, 13, 820131-820131 (2022-03-08)
Coronavirus disease 2019 (COVID-19) is currently a worldwide emergency caused by Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2). In observational clinical studies, statins have been identified as beneficial to hospitalized patients with COVID-19. However, experimental evidence of underlying statins protection
Bingjiao Zhao et al.
Journal of applied biomaterials & functional materials, 18, 2280800019900094-2280800019900094 (2020-09-16)
Simvastatin (SIM) has been documented to induce the osteogenic differentiation of periodontal ligament stem cells (PDLSCs). To establish an efficient release system for periodontal regeneration, a polycaprolactone (PCL) membrane scaffold containing SIM was electrospun and evaluated. The obtained PCL-SIM membrane
Patrícia M R Pereira et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 26(23), 6215-6229 (2020-10-02)
Statins are cholesterol-depleting drugs used to treat patients with hypercholesterolemia. Preclinically, statins disrupt trafficking of receptors present at the cell membrane. Membrane receptors, defined as tumor biomarkers and therapeutic targets, are often internalized by an endocytic pathway. Indeed, receptor endocytosis
Bing-jiao Zhao et al.
Fundamental & clinical pharmacology, 28(5), 583-592 (2013-10-12)
Periodontal ligament stem cells (PDLSCs) are considered as potential mesenchymal stem cell sources for future clinical applications in periodontal regeneration therapy. Simvastation, widely used for lowering serum cholesterol, is known to have a bone stimulatory effect. However, it is not

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