567020
Simvastatin
≥98% (HPLC), solid, HMG-CoA reductase inhibitor, Calbiochem®
别名:
Simvastatin, MK-733, L-Type Calcium Channel Blocker VI
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关于此项目
经验公式（希尔记法）:
C25H38O5
化学文摘社编号:
分子量:
418.57
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
产品名称
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
Biochem/physiol Actions
Cell permeable: no
Primary Target
farnesylation
farnesylation
Product does not compete with ATP.
Reversible: no
Disclaimer
Toxicity: Standard Handling (A)
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.
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
signalword
Warning
hcodes
Hazard Classifications
Repr. 2
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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
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
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
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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