Tamoxifen
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 574097

CAS#: 10540-29-1 (free base)

Description: Tamoxifen is a selective estrogen receptor modulator (SERM) and antagonist of ER action in breast tissue and breast cancer cells. It is reported to be effective in the treatment of early breast cancer to prevent tumor growth. Importantly, tamoxifen has been reported to act as an ER agonist in bone and blood vessels, helping to minimize osteoporosis and reduce the risk of cardiovascular disease in post-menopausal women. Also, tamoxifen is a partial ER agonist in uterine tissues and is reported to increase the risk of endometrial carcinoma.


Chemical Structure

img
Tamoxifen
CAS# 10540-29-1 (free base)

Theoretical Analysis

MedKoo Cat#: 574097
Name: Tamoxifen
CAS#: 10540-29-1 (free base)
Chemical Formula: C26H29NO
Exact Mass: 371.2249
Molecular Weight: 371.52
Elemental Analysis: C, 84.06; H, 7.87; N, 3.77; O, 4.31

Price and Availability

Size Price Availability Quantity
200.0mg USD 105.0 Ready to ship
500.0mg USD 220.0 Ready to ship
1.0g USD 375.0 Ready to ship
2.0g USD 550.0 Ready to ship
5.0g USD 850.0 Ready to ship
10.0g USD 1350.0 Ready to ship
20.0g USD 2350.0 Ready to ship
Bulk inquiry

Related CAS #: 54965-24-1 (citrate)   10540-29-1 (free base)  

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

Product Data:

Certificate of Analysis:

Safety Data Sheet (SDS):

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 53.83
Ethanol 45.0 121.12

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.

Recalculate based on batch purity %
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.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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).

Tamoxifen

200.0mg / USD 105.0


Additional Information

λmax: 238, 278 nm