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MedKoo Cat#: 100800 | Name: Tamoxifen citrate
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Description:

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

Tamoxifen, also known as ICI 46474, is an antagonist of the estrogen receptor in breast tissue via its active metabolite, 4-hydroxytamoxifen. In other tissues such as the endometrium, it behaves as an agonist, and thus may be characterized as a selective estrogen-receptor modulator. Tamoxifen is the usual endocrine (anti-estrogen) therapy for hormone receptor-positive breast cancer in pre-menopausal women, and is also a standard in post-menopausal women although aromatase inhibitors are also frequently used in that setting.

Chemical Structure

Tamoxifen citrate
Tamoxifen citrate
CAS#54965-24-1 (citrate)

Theoretical Analysis

MedKoo Cat#: 100800

Name: Tamoxifen citrate

CAS#: 54965-24-1 (citrate)

Chemical Formula: C32H37NO8

Exact Mass: 0.0000

Molecular Weight: 563.65

Elemental Analysis: C, 68.19; H, 6.62; N, 2.49; O, 22.71

Price and Availability

Size Price Availability Quantity
500mg USD 250.00 2 weeks
1g USD 350.00 2 weeks
2g USD 550.00 2 Weeks
5g USD 950.00 2 weeks
10g USD 1,250.00 2 weeks
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Related CAS #
54965-24-1 (citrate) 10540-29-1 (free base)
Synonym
ICI 46474, ICI-46474, ICI46474, NSC 180973, tamoxifen, tamoxifeni citras, Nolvadex, Novaldex
IUPAC/Chemical Name
(Z)-2-(4-(1,2-diphenylbut-1-en-1-yl)phenoxy)-N,N-dimethylethanamine 2-hydroxypropane-1,2,3-tricarboxylate
InChi Key
FQZYTYWMLGAPFJ-OQKDUQJOSA-N
InChi Code
InChI=1S/C26H29NO.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-18H,4,19-20H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25-;
SMILES Code
CC/C(C1=CC=CC=C1)=C(C2=CC=C(OCCN(C)C)C=C2)\C3=CC=CC=C3.O=C(CC(C(O)=O)(O)CC(O)=O)O
Appearance
White to off-white crystalline powder
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, not in water
Shelf Life
>2 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
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#A21K06S28
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Tamoxifen Citrate (ICI 46474) is a selective estrogen receptor modulator (SERM), potent Hsp90 activator, and inhibits infectious EBOV Zaire and Marburg (MARV) with IC50 of 0.1 µM and 1.8 µM, respectively
In vitro activity:
The effects of estrogen on LAM or angiomyolipoma cell growth have not been previously studied in vitro. The development of a primary cell culture from a LAM-associated renal angiomyolipoma has been reported here. The growth of the angiomyolipoma cells was stimulated by tamoxifen citrate (Fig. 3B). Tamoxifen citrate at 0.2 μM stimulated cultured cell growth by approximately threefold relative to the vehicle control level at 6 days (P < 0.05). These results indicate that tamoxifen acts as an estrogen agonist in these angiomyolipoma cells, in contrast to tamoxifen's estrogen antagonist action in Eker rat-derived ELT3 cells. Tamoxifen citrate also increased p44/42 MAPK phosphorylation at 15-, 30-, 45-, and 60-min time points (Fig. 4B), suggesting that tamoxifen and estradiol are signaling through common cellular pathways. This is consistent with the hypothesis that tamoxifen acts as an estrogen agonist in angiomyolipoma cells. After tamoxifen citrate treatment, increased expression of c-myc was also seen at 8 h in the angiomyolipoma cells, again without a change in cyclin D1 (Fig. 5B). It has been reported here that cells derived from a sporadic LAM-associated angiomyolipoma grew in response to tamoxifen citrate. This data indicates that tamoxifen citrate stimulates both genomic, transcriptional responses (increased expression of c-myc) and nongenomic, cytoplasmic responses (rapid activation of p44/42 MAPK) in cultured angiomyolipoma cells. Reference: Am J Physiol Lung Cell Mol Physiol. 2004 Apr;286(4):L694-700. https://pubmed.ncbi.nlm.nih.gov/12922981/
In vivo activity:
The aim of this study was to evaluate the effects of tamoxifen citrate on gene expression during nuclear chromatin condensation in male rats. The effects of an oral dose of 0.4 kg/(kg.d) tamoxifen citrate on rates of in vitro chromatin decondensation, acridine orange (AO) dye uptake, concentration of thiol-groups, levels and/or expression of transition proteins 1, 2 (TP1, TP2), protamine 1 (P1), cyclic AMP response element modulator-tau (CREMtau), androgen-binding protein (ABP) and cyclic adenosine 3',5' monophosphate (cAMP) were evaluated after 60 days of exposure in adult male rats. Controls received the vehicle. Tamoxifen citrate enhanced the rates of chromatin decondensation, increased AO dye uptake and reduced free thiols in caput epididymal sperms and reduced the levels of TP1, TP2, P1, and CREMtau in the testis, while cAMP was unaffected. P1 deposition was absent in the sperm. The transcripts of TP1, TP2 were increased, of P1 and ABP decreased, while those of CREMtau unaffected in the testis. Tamoxifen citrate reduced caput epididymal sperm chromatin compaction by reducing the testicular levels of proteins TP1, TP2 and P1 and the CREMtau involved in chromatin condensation during spermiogenesis. Tamoxifen citrate affects the expression of these genes at both the transcriptional and post-transcriptional levels. Reference: Asian J Androl. 2005 Sep;7(3):311-21. https://pubmed.ncbi.nlm.nih.gov/16110360/
Solvent mg/mL mM
Solubility
DMSO 50.0 88.70
Ethanol 10.0 17.70
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 563.65 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. Hawariah A, Stanslas J. In vitro response of human breast cancer cell lines to the growth-inhibitory effects of styrylpyrone derivative (SPD) and assessment of its antiestrogenicity. Anticancer Res. 1998 Nov-Dec;18(6A):4383-6. PMID: 9891496. 2. Yu J, Astrinidis A, Howard S, Henske EP. Estradiol and tamoxifen stimulate LAM-associated angiomyolipoma cell growth and activate both genomic and nongenomic signaling pathways. Am J Physiol Lung Cell Mol Physiol. 2004 Apr;286(4):L694-700. doi: 10.1152/ajplung.00204.2003. Epub 2003 Aug 15. PMID: 12922981. 3. Aleem M, Padwal V, Choudhari J, Balasinor N, Parte P, Gill-Sharma M. Effects of tamoxifen citrate on gene expression during nuclear chromatin condensation in male rats. Asian J Androl. 2005 Sep;7(3):311-21. doi: 10.1111/j.1745-7262.2005.00027.x. PMID: 16110360. 4. Karaca T, Gözalan AU, Yoldaş Ö, Bilgin BÇ, Tezer A. Effects of tamoxifen citrate on postoperative intra-abdominal adhesion in a rat model. Int J Surg. 2013;11(1):68-72. doi: 10.1016/j.ijsu.2012.11.015. Epub 2012 Dec 2. PMID: 23211136.
In vitro protocol:
1. Hawariah A, Stanslas J. In vitro response of human breast cancer cell lines to the growth-inhibitory effects of styrylpyrone derivative (SPD) and assessment of its antiestrogenicity. Anticancer Res. 1998 Nov-Dec;18(6A):4383-6. PMID: 9891496. 2. Yu J, Astrinidis A, Howard S, Henske EP. Estradiol and tamoxifen stimulate LAM-associated angiomyolipoma cell growth and activate both genomic and nongenomic signaling pathways. Am J Physiol Lung Cell Mol Physiol. 2004 Apr;286(4):L694-700. doi: 10.1152/ajplung.00204.2003. Epub 2003 Aug 15. PMID: 12922981.
In vivo protocol:
1. Aleem M, Padwal V, Choudhari J, Balasinor N, Parte P, Gill-Sharma M. Effects of tamoxifen citrate on gene expression during nuclear chromatin condensation in male rats. Asian J Androl. 2005 Sep;7(3):311-21. doi: 10.1111/j.1745-7262.2005.00027.x. PMID: 16110360. 2. Karaca T, Gözalan AU, Yoldaş Ö, Bilgin BÇ, Tezer A. Effects of tamoxifen citrate on postoperative intra-abdominal adhesion in a rat model. Int J Surg. 2013;11(1):68-72. doi: 10.1016/j.ijsu.2012.11.015. Epub 2012 Dec 2. PMID: 23211136.
1: Hassani-Abharian P, Hejazi Dehaghani S, Shahmoradi Z, Hejazi SH. Therapeutic effect of topical tamoxifen in murine cutaneous leishmaniasis caused by Leishmania major. Antimicrob Agents Chemother. 2024 Dec 5;68(12):e0035824. doi: 10.1128/aac.00358-24. Epub 2024 Oct 24. PMID: 39445817; PMCID: PMC11619401. 2: Ashin ZF, Sadeghi-Mohammadi S, Vaezi Z, Najafi F, AdibAmini S, Sadeghizadeh M, Naderi-Manesh H. Synergistic effect of curcumin and tamoxifen loaded in pH- responsive gemini surfactant nanoparticles on breast cancer cells. BMC Complement Med Ther. 2024 Sep 20;24(1):337. doi: 10.1186/s12906-024-04631-x. PMID: 39304876; PMCID: PMC11415995. 3: Luo J, Luo Y, Dong C, Qi G, Zhong L, Liu F, Wen W. Enhancing Sperm Motility Parameters in Patients with Asthenospermia: A Combined Approach of Acupuncture at Fusiguan Point and Tamoxifen Citrate Tablets. Arch Esp Urol. 2024 Mar;77(2):142-147. doi: 10.56434/j.arch.esp.urol.20247702.19. PMID: 38583006. 4: Abd El-Sadek I, Morishita R, Mori T, Makita S, Mukherjee P, Matsusaka S, Yasuno Y. Label-free visualization and quantification of the drug-type-dependent response of tumor spheroids by dynamic optical coherence tomography. Sci Rep. 2024 Feb 9;14(1):3366. doi: 10.1038/s41598-024-53171-4. PMID: 38336794; PMCID: PMC10858208. 5: Twal S, Jaber N, Al-Remawi M, Hamad I, Al-Akayleh F, Alshaer W. Dual stimuli- responsive polymeric nanoparticles combining soluplus and chitosan for enhanced breast cancer targeting. RSC Adv. 2024 Jan 18;14(5):3070-3084. doi: 10.1039/d3ra08074a. PMID: 38239437; PMCID: PMC10795518. 6: Beeraka NM, Zhang J, Mandal S, Vikram P R H, Liu J, B M N, Zhao D, Vishwanath P, B M G, Fan R. Screening fructosamine-3-kinase (FN3K) inhibitors, a deglycating enzyme of oncogenic Nrf2: Human FN3K homology modelling, docking and molecular dynamics simulations. PLoS One. 2023 Nov 1;18(11):e0283705. doi: 10.1371/journal.pone.0283705. PMID: 37910519; PMCID: PMC10619859. 7: Nasr M, Hashem F, Teiama M, Tantawy N, Abdelmoniem R. Folic acid grafted mixed polymeric micelles as a targeted delivery strategy for tamoxifen citrate in treatment of breast cancer. Drug Deliv Transl Res. 2024 Apr;14(4):945-958. doi: 10.1007/s13346-023-01443-3. Epub 2023 Oct 31. PMID: 37906415; PMCID: PMC10927891. 8: Khan SA, Mi X, Xu Y, Blanco LZ Jr, Akasha AM, Pilewskie M, Degnim AC, AlHilli Z, Amin AL, Hwang ES, Guenther JM, Kocherginsky M, Benante K, Zhang S, Helland T, Hustad SS, Gursel DB, Mellgren G, Dimond E, Perloff M, Heckman-Stoddard BM, Lee O. Presurgical Oral Tamoxifen vs Transdermal 4-Hydroxytamoxifen in Women With Ductal Carcinoma In Situ: A Randomized Clinical Trial. JAMA Surg. 2023 Dec 1;158(12):1265-1273. doi: 10.1001/jamasurg.2023.5113. PMID: 37870954; PMCID: PMC10594180. 9: Ji Y, Zhao H, Liu H, Zhao P, Yu DG. Electrosprayed Stearic-Acid-Coated Ethylcellulose Microparticles for an Improved Sustained Release of Anticancer Drug. Gels. 2023 Aug 29;9(9):700. doi: 10.3390/gels9090700. PMID: 37754381; PMCID: PMC10528259. 10: Kumar G, Mullick P, Nandakumar K, Mutalik S, Chamallamudi MR. Box-Behnken Design-Aided Validation and Optimization of a Stability-Indicating Reverse Phase-HPLC Method for the Estimation of Tamoxifen Citrate in Lipidic Nano- Vesicles. J Chromatogr Sci. 2023 Nov 5;61(9):827-837. doi: 10.1093/chromsci/bmad059. PMID: 37554069. 11: Shokei TA. Editorial Expression of Concern: Tamoxifen citrate for women with unexplained infertility. Arch Gynecol Obstet. 2023 Oct;308(4):1387. doi: 10.1007/s00404-023-07161-y. PMID: 37526686. 12: Zhou JB, Tang D, He L, Lin S, Lei JH, Sun H, Xu X, Deng CX. Machine learning model for anti-cancer drug combinations: Analysis, prediction, and validation. Pharmacol Res. 2023 Aug;194:106830. doi: 10.1016/j.phrs.2023.106830. Epub 2023 Jun 19. PMID: 37343647. 13: Ortiz-Miravalles L, Sánchez-Angulo M, Sanz JM, Maestro B. Drug Repositioning as a Therapeutic Strategy against Streptococcus pneumoniae: Cell Membrane as Potential Target. Int J Mol Sci. 2023 Mar 18;24(6):5831. doi: 10.3390/ijms24065831. PMID: 36982905; PMCID: PMC10058218. 14: Kavya D, Nadumane VK. A combination of semi-purified L-methioninase with tamoxifen citrate to ameliorate breast cancer in athymic nude mice. Mol Biol Rep. 2023 Mar;50(3):2925-2932. doi: 10.1007/s11033-022-08144-z. Epub 2022 Dec 24. PMID: 36566301. 15: Aljassim FK, El-Sheikh AA, Motabagani MA. The Effect of Tamoxifen Citrate on Granulosa Cells of Ovarian Follicles in Adult Female Rats: Light Microscopic Study. J Microsc Ultrastruct. 2022 Nov 9;12(1):1-5. doi: 10.4103/jmau.jmau_79_21. PMID: 38633571; PMCID: PMC11019587. 16: Younis MEM, Jaber FA, Majrashi KA, Ghoneim HA, Shukry M, Shafi ME, Albaqami NM, Abd El-Hack ME, Abo Ghanima MM. Impacts of synthetic androgen and estrogenic antagonist administration on growth performance, sex steroids hormones, and immune markers of male and female broilers. Poult Sci. 2023 Jan;102(1):102244. doi: 10.1016/j.psj.2022.102244. Epub 2022 Oct 13. PMID: 36335738; PMCID: PMC9640317. 17: Suárez DF, Pinzón-García AD, Sinisterra RD, Dussan A, Mesa F, Ramírez- Clavijo S. Uniaxial and Coaxial Nanofibers PCL/Alginate or PCL/Gelatine Transport and Release Tamoxifen and Curcumin Affecting the Viability of MCF7 Cell Line. Nanomaterials (Basel). 2022 Sep 26;12(19):3348. doi: 10.3390/nano12193348. PMID: 36234476; PMCID: PMC9565524. 18: Kahlous Y, Palanirajan VK, Starlin M, Negi JS, Cheah SC. Preparation and Characterization of Chitosan and Inclusive Compound-Layered Gold Nanocarrier to Improve the Antiproliferation Effect of Tamoxifen Citrate in Colorectal Adenocarcinoma (Caco-2) and Breast Cancer (MCF-7) Cells. Turk J Pharm Sci. 2022 Aug 31;19(4):391-399. doi: 10.4274/tjps.galenos.2021.48961. Erratum in: Turk J Pharm Sci. 2023 May 9;20(2):126. doi: 10.4274/tjps.galenos.2023.48961.e001. PMID: 36047535; PMCID: PMC9438755. 19: Aekrungrueangkit C, Wangngae S, Kamkaew A, Ardkhean R, Thongnest S, Boonsombat J, Ruchirawat S, Khotavivattana T. Novel psoralen derivatives as anti-breast cancer agents and their light-activated cytotoxicity against HER2 positive breast cancer cells. Sci Rep. 2022 Aug 5;12(1):13487. doi: 10.1038/s41598-022-17625-x. PMID: 35931753; PMCID: PMC9356065. 20: Alyami MH, Alyami HS, Alshehri AA, Alsharif WK, Shaikh IA, Algahtani TS. Tamoxifen Citrate Containing Topical Nanoemulgel Prepared by Ultrasonication Technique: Formulation Design and In Vitro Evaluation. Gels. 2022 Jul 21;8(7):456. doi: 10.3390/gels8070456. PMID: 35877541; PMCID: PMC9316521.