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S6196

Sigma-Aldrich

辛伐他汀

≥97% (HPLC), solid

同義詞:

MK-733, SVA

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About This Item

經驗公式（希爾表示法）:
C25H38O5
CAS號碼:
79902-63-9
分子量：:
418.57
MDL號碼:
MFCD00072007
分類程式碼代碼:
12352200
PubChem物質ID:
24724617
NACRES:
NA.77
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化驗

≥97% (HPLC)

形狀

solid

顏色

white

mp

127-132 °C (lit.)

溶解度

DMSO: ≥20 mg/mL

起源

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

儲存溫度

2-8°C

SMILES 字串

[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 密鑰

RYMZZMVNJRMUDD-HGQWONQESA-N

基因資訊

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

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一般說明

辛伐他汀是药物前体。辛伐他汀是洛伐他汀的半合成衍生物/类似物。辛伐他汀不溶于水，但可溶于极性有机溶剂。[1]

應用

辛伐他汀已用于：
  • 用于 HMG CoA还原酶(HMGCR)的抑制剂[2]
  • 研究其对上皮间质转化(EMT)以及肺腺癌患者预后的影响[3]
  • 体内研究检验其对脑肿瘤−启动细胞(BTIC)活力和细胞增殖的影响[4]
  • 研究三磷酸腺苷(ATP)-结合盒转运蛋白A7在Jurkat细胞吞噬作用中的作用
  • 研究其对小鼠内皮功能障碍和炎症的影响

生化／生理作用

辛伐他汀是HMG-CoA还原酶和降胆固醇药物的特异性抑制剂。
辛伐他汀是HMG-CoA还原酶的特异性抑制剂[2]，HMG-CoA还原酶是催化HMG-CoA转化为甲羟戊酸的酶，其是胆固醇生物合成的早期步骤。由于它可以降低低密度脂蛋白胆固醇和甘油三酯的水平，并提高高密度脂蛋白水平，因而可用于治疗高胆固醇血症[1]。辛伐他汀是一种内酯，其在体内易于水解成相应的β-羟基酸，并可以在使用前用溶于EtOH中的NaOH进行活化。它还可能对内皮功能、炎症、平滑肌细胞功能、血管壁功能[5]\止血和LDL氧化具有有益作用。
辛伐他汀是HMG-CoA还原酶的特异性抑制剂，HMG-CoA还原酶是催化HMG-CoA转化为甲羟戊酸的酶，其是胆固醇生物合成的早期步骤。由于它可以降低低密度脂蛋白和甘油三酯的水平，并提高高密度脂蛋白水平，因而可用于治疗高胆固醇血症。辛伐他汀是一种内酯，其在体内 易于水解成相应的β-羟基酸，并可以在使用前用溶于EtOH中的NaOH进行活化。它是洛伐他汀的合成类似物（货M2147）。

特點和優勢

该化合物是由Merck & Co., Inc., Kenilworth, NJ, U.S.开发的。想要浏览其他由制药公司开发的化合物以及已批准药物/候选药物清单， 请单击此处。

象形圖

Health hazard
GHS08

訊號詞

Warning

危險聲明

H361d

危險分類

Repr. 2

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

Eyeshields, Gloves, type N95 (US)

從最近期的版本中選擇一個：

分析證明 (COA)

Lot/Batch Number
0000439034
0000439034
0000420940
0000420940
0000400586

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存取文件庫

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)
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)
Statins and Cardiovascular Diseases: From Cholesterol Lowering to Pleiotropy
Zhou Q, et al.
Current Pharmaceutical Design, 15(5), 467-467 (2009)
Kirill Tarasov et al.
The Journal of clinical endocrinology and metabolism, 99(1), E45-E52 (2013-11-19)
Coronary artery disease (CAD) is among the leading causes of mortality and morbidity worldwide. Traditional risk markers explain only a proportion of total cardiovascular risk. Thus, development and improvement of early diagnostic strategies and targeted initiation of preventive measures would
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Questions

1–7 of 7 Questions  

  1. Can S6196 be used for cell culture assays?

    1 answer

    1. This item has not been tested for use in cell culture. However, the product has been used successfully for in vitro and in vivo applications by other researchers. Please see the links below to review example publications:
      MYC-regulated mevalonate metabolism maintains brain tumor-initiating cells
      https://pmc.ncbi.nlm.nih.gov/articles/PMC5600855/

      Effects of simvastatin on retinal structure and function of a high-fat atherogenic mouse model of thickened Bruch's membrane.
      https://pubmed.ncbi.nlm.nih.gov/24398101/

      Helpful?

  2. How can S6196 be stored for long term storage after DMSO resuspension?

    1 answer

    1. The solubility of this material has not been tested in DMSO. However, external sources report that Simvastatin is soluble in DMSO at >50 mg/mL. Stock solutions may be stored in DMSO at -20°C for at least 1 month. This information has not been validated. As a general rule, avoid repeated freeze/thaw cycles.

      Helpful?

  3. What happens when the drug is not activated before use in in vitro experiments?

    1 answer

    1. This material does not require activation for cell-based in vitro studies, as it is readily hydrolyzed by the cells. For experiments without live cells the product will remain inactive. This material may be chemically activated per M. Sadeghi et al., J. Immunol., 165, 2712-2718 (2000) as noted below:
      1. 4 mg of simvastatin is dissolved in 100 μl of ethanol.
      2. Then 150 μl of 0.1 N NaOH was added to the solution and subsequently incubated at 50 °C for 2 hours.
      3. The pH was brought to 7.0 by HCl, and the final concentration of the stock solution was adjusted to 4 mg/ml. The stock solution was kept at 4 °C.

      Helpful?

  4. What is the solution stability of Product S6196, Simvastatin, in various solvents?

    1 answer

    1. Sigma-Aldrich has not determined the solution stability of simvastatin. One publication on the subject, published by Yang, H. et al., reports that a 50 mg/mL stock solution of simvastatin in methanol was stored for one month at 4°C. Reference: Determination of Simvastatin in human plasma by liquid chromatography-mass spectrometry.  J. Chromatography B, 785(2), 369-375 (2003).

      Helpful?

  5. How is Product S6196, Simvastatin, activated?

    1 answer

    1. An activation procedure from M. Sadeghi, et al., J. Immunol., 165, 2712-2718 (2000) is:1. 4 mg of simvastatin is dissolved in 100 μl of ethanol.2. Then 150 μl of 0.1 N NaOH was added to the solution and subsequently incubated at 50 °C for 2 hours.3. The pH was brought to 7.0 by HCl, and the final concentration of the stock solution was adjusted to 4 mg/ml. The stock solution was kept at 4 °C.

      Helpful?

  6. What is Product S6196, Simvastatin, soluble in?

    1 answer

    1. According to the chemicals encyclopedia published by the Royal Society of Chemistry, 14th ed., Entry # 8539, simvastatin is soluble in chloroform at 610 mg/mL, DMSO at 540 mg/mL, methanol at 200 mg/mL, ethanol at 160 mg/mL, 0.1 M HCl at 60 μg/mL, PEG-400 at 70 mg/mL, 0.1 M NaOH at 70 mg/mL, and water at 30 μg/mL. Please note that some of the values are given in milligrams per mL and others are in micrograms per mL.

      Helpful?

  7. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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