This product is soluble in DMSO or ethanol at a concentration of 50 mg/mL. Treatment with NaOH in ethanol is required, followed by neutralization to pH 7.2 for activation.
567020
Simvastatin
≥98% (HPLC), solid, HMG-CoA reductase inhibitor, Calbiochem®
Synonym(s):
Simvastatin, MK-733, L-Type Calcium Channel Blocker VI
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50 MG
$318.00
$318.00
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About This Item
Empirical Formula (Hill Notation):
C25H38O5
CAS Number:
Molecular Weight:
418.57
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
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Product Name
Simvastatin, A lipophilic 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitor that blocks Ras function through inhibition of farnesylation.
Quality Level
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
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
Related Categories
1 of 4
This Item | S0650000 | BP739 | Y0002069 |
|---|---|---|---|
| form solid | form - | form powder | form - |
| assay ≥98% (HPLC) | assay - | assay - | assay - |
| Quality Level 100 | Quality Level - | Quality Level - | Quality Level - |
| manufacturer/tradename Calbiochem® | manufacturer/tradename EDQM | manufacturer/tradename BP | manufacturer/tradename EDQM |
| storage temp. 2-8°C | storage temp. - | storage temp. −20°C | storage temp. 2-8°C |
| storage condition OK to freeze | storage condition - | storage condition - | storage condition - |
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.
Biochem/physiol Actions
Cell permeable: no
Primary Target
farnesylation
farnesylation
Product does not compete with ATP.
Reversible: no
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.
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.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
signalword
Warning
hcodes
Hazard Classifications
Repr. 2
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (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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Can I dissolve Simvastatin powder in DMSO and then activate it through NaOH treatment?
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