Synonym
Tamoxifen;ICI 46474, ICI-46474, ICI46474, NSC 180973, tamoxifen, tamoxifeni citras, Nolvadex, Novaldex
IUPAC/Chemical Name
2-[4-[(1Z)-1,2-diphenyl-1-buten-1-yl]phenoxy]-N,N-dimethyl-ethanamine
InChi Key
NKANXQFJJICGDU-QPLCGJKRSA-N
InChi Code
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 Code
CC/C(C1=CC=CC=C1)=C(C2=CC=CC=C2)/C3=CC=C(OCCN(C)C)C=C3v
Appearance
A crystalline solid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Tamoxifen (ICI 47699) is a selective estrogen receptor modulator (SERM) that is a potent Hsp90 activator and enhances the Hsp90 molecular chaperone ATPase activity as well as inhibits infectious EBOV Zaire and Marburg (MARV) with IC50 of 0.1 µM and 1.8 µM, respectively.
In vitro activity:
Gallbladder cancer cells treated with TAM (Tamoxifen) indeed induced AMPK activation, which was accompanied by decreased phosphorylation of mTOR (p‐mTOR) (Figure3E), a critical regulator of cancer cell glycolysis, indicating impaired glycolysis. To determine whether the effect of glycolysis inhibition by TAM was dependent on the upstream activation of ROS, the level of pAMPK was measured in GBC cells treated with TAM alone or along with NAC. As shown in Figure 3F, addition of NAC significantly attenuated the phosphorylation of AMPK induced by TAM. Importantly, NAC also recovered the glucose uptake and the production of lactate down‐regulated by TAM treatment, which were consistent with the effect of NAC on TAM‐induced apoptosis (Figure3G). Together, these data provide evidence that TAM promoted GBC apoptosis through impaired glycolysis via ROS production. Since we have demonstrated TAM suppresses glycolysis via activation of AMPK, compound C (AMPK inhibitor) and AMPK knockdown were used to further evaluate whether the AMPK signalling pathway is required for TAM‐induced suppression of GBC cells. As shown, AMPK inhibitor compound C (CC) reversed the pro‐apoptotic effect of TAM (Figure3H,I). In lines with the effect, CC dramatically abrogated AMPK phosphorylation (Figure3J).GBC cells with AMPK knockdown also exhibited stronger resistance to TAM (Figure3K,L). Taken together, these data indicated that TAM inhibited GBC cell growth largely by activating AMPK signalling.
J Cell Mol Med. 2020 Jan; 24(2): 1599–1613. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6991689/
In vivo activity:
To further illustrate the curative effect of tamoxifen for different HO progression stages, mice were administered with tamoxifen (9 mg/kg) every other day for a total of 3 weeks post puncture at different stages of HO progression mainly including inflammatory stage (Day 1–Week 3), chondrogenesis stage (Week 4–Week 6), osteogenesis stage (Week 7–Week 9) and maturation stage (Week 10– Week 12) . Analysis of samples scanned by μCT revealed that the bone volume of HO was both significantly decreased in mice with the treatment of tamoxifen from day 1 and week 4, respectively (p<0.05) (Figure 3A, 3B), whereas no significant reduction was found at week 7 and week 10 groups compared to vehicle-treated mice (Figure 3B). The bone marrow cavity showed by H&E staining was diminished with the treatment of tamoxifen from day 1 and week 4 relative to week 7, week 10 and vehicle groups (Figure 3C). In addition, the number of Ocn+ osteoblasts (Figure 3D, 3E) and p-Smad2/3+ cells (Figure 3F–3I) were both significantly reduced in mice treated with tamoxifen at inflammatory and chondrogenesis stages relative to vehicle-administered mice (p<0.05), showed an inhibitory bone propagation. The downtrends in Ocn and p-Smad2/3 protein levels are consistent with immunohistochemistry results, and administration of tamoxifen at different periods can significantly improve the activity of ERα (Figure 3J). Collectively, all these results demonstrated that HO propagation could be attenuated by tamoxifen at the early stages of inflammation and chondrogenesis accompanied with the TGF-β signaling pathway was suppressed by ERα.
Med Sci Monit. 2019; 25: 7872–7881. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6820362/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
20.0 |
53.83 |
| Ethanol |
45.0 |
121.12 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
371.52
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Weinstock A, Gallego-Delgado J, Gomes C, Sherman J, Nikain C, Gonzalez S, Fisher E, Rodriguez A. Tamoxifen activity against Plasmodium in vitro and in mice. Malar J. 2019 Nov 27;18(1):378. doi: 10.1186/s12936-019-3012-7. PMID: 31775753; PMCID: PMC6882195. 2. Huang S, Wang H, Chen W, Zhan M, Xu S, Huang X, Lin R, Shen H, Wang J. Tamoxifen inhibits cell proliferation by impaired glucose metabolism in gallbladder cancer. J Cell Mol Med. 2020 Jan;24(2):1599-1613. doi: 10.1111/jcmm.14851. Epub 2019 Nov 28. PMID: 31782270; PMCID: PMC6991689.
3.Weinstock A, Gallego-Delgado J, Gomes C, Sherman J, Nikain C, Gonzalez S, Fisher E, Rodriguez A. Tamoxifen activity against Plasmodium in vitro and in mice. Malar J. 2019 Nov 27;18(1):378. doi: 10.1186/s12936-019-3012-7. PMID: 31775753; PMCID: PMC6882195.
4. Mao D, Mi J, Pan X, Li F, Rui Y. Tamoxifen Inhibits the Progression of Trauma-Induced Heterotopic Ossification in Mice. Med Sci Monit. 2019 Oct 21;25:7872-7881. doi: 10.12659/MSM.916733. PMID: 31631887; PMCID: PMC6820362.
In vitro protocol:
1. Weinstock A, Gallego-Delgado J, Gomes C, Sherman J, Nikain C, Gonzalez S, Fisher E, Rodriguez A. Tamoxifen activity against Plasmodium in vitro and in mice. Malar J. 2019 Nov 27;18(1):378. doi: 10.1186/s12936-019-3012-7. PMID: 31775753; PMCID: PMC6882195. 2. Huang S, Wang H, Chen W, Zhan M, Xu S, Huang X, Lin R, Shen H, Wang J. Tamoxifen inhibits cell proliferation by impaired glucose metabolism in gallbladder cancer. J Cell Mol Med. 2020 Jan;24(2):1599-1613. doi: 10.1111/jcmm.14851. Epub 2019 Nov 28. PMID: 31782270; PMCID: PMC6991689.
In vivo protocol:
1.Weinstock A, Gallego-Delgado J, Gomes C, Sherman J, Nikain C, Gonzalez S, Fisher E, Rodriguez A. Tamoxifen activity against Plasmodium in vitro and in mice. Malar J. 2019 Nov 27;18(1):378. doi: 10.1186/s12936-019-3012-7. PMID: 31775753; PMCID: PMC6882195.
2. Mao D, Mi J, Pan X, Li F, Rui Y. Tamoxifen Inhibits the Progression of Trauma-Induced Heterotopic Ossification in Mice. Med Sci Monit. 2019 Oct 21;25:7872-7881. doi: 10.12659/MSM.916733. PMID: 31631887; PMCID: PMC6820362.
1. Horwitz, K.B., and McGuire, W.L. Nuclear mechanisms of estrogen action. Effects of estradiol and anti-estrogens on estrogen receptors and nuclear receptor processing. The Journal of Biological Chemisty 253(22), 8185-8191 (1978).
2. Clarke, M., Collins, R., Davies, C., et al. Tamoxifen for early breast cancer: An overview of the randomised trials. Lancet 351, 1451-1467 (1998).
3. Tonetti, D.A., and Jordan, V.C. Targeted anti-estrogens to treat and prevent diseases in women. Mol. Med. Today 2(5), 218-223 (1996).
4. Jordan, V.C., and Assikis, V.J. Endometrial carcinoma and tamoxifen: Clearing up a controversy. Clinical Cancer Research 1(5), 467-472 (1995).
