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Merck
CN

T5648

泰莫西芬

≥99% (TLC), powder, PKC inhibitor

别名:

反式他莫昔芬, (Z)-1-(对二甲基氨基乙氧基苯基)-1,2-二苯基-1-丁烯, (Z)-2-[4-(1,2-二苯基-1-丁烯)苯氧基]-N,N-二甲基乙胺

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关于此项目

线性分子式:
C6H5C(C2H5)=C(C6H5)C6H4OCH2CH2N(CH3)2
化学文摘社编号:
10540-29-1
分子量:
371.51
NACRES:
NA.54
PubChem Substance ID:
24900307
UNSPSC Code:
12161501
EC Number:
234-118-0
MDL number:
MFCD00010454

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产品名称

泰莫西芬, ≥99%

InChI key

NKANXQFJJICGDU-QPLCGJKRSA-N

InChI

1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-

SMILES string

CC\C(c1ccccc1)=C(/c2ccccc2)c3ccc(OCCN(C)C)cc3

sterility

(Not packaged in a sterile environment)

assay

≥99%

mp

97-98 °C (lit.)

solubility

H2O: insoluble <0.1% at 20 °C
chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow
2-propanol: soluble
DMSO: soluble
ethanol: soluble
methanol: soluble
propylene glycol: soluble

antibiotic activity spectrum

neoplastics

mode of action

enzyme | inhibits

originator

AstraZeneca

storage temp.

2-8°C

Gene Information

human ... CYP1A2(1544), EBP(10682), ESR1(2099), ESR2(2100), ESRRA(2101)
rat ... Ar(24208), Esr1(24890)

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相关类别

Application

他莫昔芬已用于：
  • MTS (3-(4,5-二甲基噻唑-2-基)-5-(3-羧基甲氧基苯基)-2-(4-磺酸苯基)-2H-四唑) 试验和结晶紫染色试验，以评估细胞活力。
  • 诱导Dicer条件性敲除小鼠中的Dicer消融，以研究Dicer缺乏对脂肪细胞分化和功能的作用。
  • 研究其对来源于T细胞急性成淋巴细胞性白血病（T-ALL）的耐糖皮质激素（GC）细胞系Jurkat的生物学作用。
  • 研究他莫昔芬治疗对小鼠中雌激素受体α（ERα）介导的下丘脑-POA的生理学作用。
  • 诱导Cre重组酶活性进行基因操控。
  • 促进ect2flox等位基因在小鼠器官中的重组。
  • 研究其对脂多糖（LPS）诱导的小胶质细胞激活的影响。

Biochem/physiol Actions

乳腺中的雌激素拮抗剂。阻止乳腺肿瘤细胞中的雌二醇刺激的 VEGF 的产生。蛋白激酶 C 抑制剂。
蛋白激酶 C 抑制剂。诱发人类恶性神经胶质瘤细胞系的细胞凋亡。他莫昔芬及其代谢产物 4-羟基他莫昔芬是选择性雌激素反应调节剂 (SERM)，在乳腺中用作雌激素拮抗剂。阻止乳腺肿瘤细胞中雌二醇刺激的 VEGF 的产生。

Features and Benefits

该化合物是ADME Tox研究的特色产品。点击此处以发现更多的ADME Tox特色产品。可访问sigma.com/discover-bsm了解更多关于用于其他研究领域生物活性小分子。
该化合物由AstraZeneca开发。如需浏览其他药物开发的化合物和批准的药物/候选药物清单，请单击此处。

General description

他莫昔芬(TC)是一种选择性雌激素受体调节剂(SERM)，用于治疗男性和女性乳腺癌。还可作为女性的癌症预防药物。这种蛋白激酶C抑制剂和抗血管生成因子是一种前药，可通过细胞色素P450酶的同工型CYP2D6和CYP3A4代谢成活性代谢产物4-羟基他莫昔芬(4-OHT)和内昔芬。在乳腺癌中，他莫昔芬针对ERBB2的基因阻遏活性依赖于PAX2。在乳腺癌细胞中，他莫昔芬抑制雌二醇诱导的血管内皮生长因子受体(VEGF)生成。雌激素受体阳性肿瘤患者更有可能受益于他莫昔芬治疗。通过选择性结合机体不同部位的雌激素受体，他莫昔芬具有雌激素激动剂和拮抗剂作用。

这种非类固醇三苯乙烯衍生物可抑制肿瘤生长，据报道是一种动物致癌物和致畸物。此外，他莫昔芬还保护骨骼免遭雌激素缺乏的骨丢失，降低血浆胆固醇，并参与大鼠的肝脏癌变过程。他莫昔芬的其他作用包括降低胰岛素样生长因子的血浆水平，诱导癌细胞包围的细胞分泌转化生长因子β，抑制膜脂质过氧化（可能通过降低膜流动性发挥作用）。

Other Notes

2024年CiteAb奖——成功的帕金森研究供应商(2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research)
本品并未在无菌环境下包装。

Preparation Note

他莫昔芬可以50 mg/ml溶于氯仿并产生一种透明无色至淡黄色的溶液。它还可溶于甲醇、乙醇、2-丙醇和丙二醇。他莫昔芬的储备溶液可按10 mM制备于DMSO中。然而，它几乎不溶于水（溶解度是<0.01%, 20° C）。溶液对紫外光敏感，而DMSO溶液可避光稳定储存在 -20° C。
他莫昔芬相对稳定。粉末可在2-8℃下避光干燥稳定保存至少两年。

pictograms

Health hazardEnvironment
GHS08,GHS09

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Repr. 1B

存储类别

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

法规信息

涉药品监管产品
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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000521686
0000521686
WXBF7866V
0000499602
0000499602

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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

    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. 

  5. What is the solubility of tamoxifen, Product No. T5648?

    Tamoxifen is tested for solubility in chloroform at a concentration of 50mg/mL.  This yields a colorless to faint yellow solution.  Tamoxifen is practically insoluble in water.  It has been reported to be soluble in methanol, ethanol, 2-propanol and propylene glycol.  This product is also reported to be soluble in DMSO at 10mM concentration.  Reference for DMSO solubility: Wong, K.R., et al., Am. J. Physiol. Heart Circ. Physiol., 277, H1403-H1409 (1999).  Please also see the product information sheet (under Documents, above) for more information on the solubility of this product.

  6. What is the stability of tamoxifen (e.g., Product No. T5648) once in solution?

    Solutions of tamoxifen are sensitive to UV light. According to C.A. O'Brian et al., [Cancer Res. 45, 2462 (1985)], tamoxifen when dissolved in DMSO can be stored at -20°C in the dark. We generally recommend making the solution fresh right before each use.

  7. How do I find the expiration date of the bottle of Product No T5648, Tamoxifen, in my possession?

    According to Sigma Quality Control Data, T5648 (tamoxifen) should be stable for at least two years if stored dessicated at 2-8°C in the dark.  However, there is not an established expiration or retest date for Tamoxifen.  This product is guaranteed for 1 year from shipment, if stored correctly and unopened.

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Meimei Liu et al.
Aquatic toxicology (Amsterdam, Netherlands), 213, 105220-105220 (2019-06-16)
Tamoxifen (TAM) is an antiestrogenic agent and can enter the aquatic environment in wastewater. It has been reported that TAM can induce hepatic steatosis in vertebrates, however, the effects of TAM exposure on lipid metabolism of hepatopancreas in crustaceans remains
Bon-Kyoung Koo et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(24), 7548-7550 (2015-05-30)
Rnf43 (RING finger protein 43) and Znrf3 (zinc/RING finger protein 3) (RZ) are two closely related transmembrane E3 ligases, encoded by Wnt target genes, that remove surface Wnt (wingless-int) receptors. The two genes are mutated in various human cancers. Such
Microglia-Specific Expression of Olfml3 Is Directly Regulated by Transforming Growth Factor ?1-Induced Smad2 Signaling
Neidert N, et al.
Frontiers in Immunology, 9, 1728-1728 (2018)
Tamoxifen
Farrar MC and Jacobs TF
StatPearls [Internet] (2023)
Takeo Nakaya et al.
Cancer research, 74(10), 2882-2891 (2014-03-15)
The intestinal epithelium maintains homeostasis by a self-renewal process involving resident stem cells, including Lgr5(+) crypt-base columnar cells, but core mechanisms and their contributions to intestinal cancer are not fully defined. In this study, we examined a hypothesized role for
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