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

MedKoo CAT#: 100800

CAS#: 54965-24-1 (citrate)

Description: 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

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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:
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
500.0mg USD 220.0 2 Weeks
1.0g USD 360.0 2 Weeks
5.0g USD 705.0 2 Weeks
10.0g USD 1250.0 2 Weeks
Bulk inquiry

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

Product Data:

Certificate of Analysis:

Safety Data Sheet (SDS):

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 88.7
Ethanol 10.0 17.7

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.

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2: Desmarais JE, Looper KJ. Interactions between tamoxifen and antidepressants via cytochrome P450 2D6. J Clin Psychiatry. 2009 Dec;70(12):1688-97. Review. PubMed PMID: 20141708.

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8: Sengupta S, Jordan VC. Selective estrogen modulators as an anticancer tool: mechanisms of efficiency and resistance. Adv Exp Med Biol. 2008;630:206-19. Review. PubMed PMID: 18637493.

9: Saynak M, Cosar-Alas R, Yurut-Caloglu V, Caloglu M, Kocak Z, Uzal C. Chemotherapy and cerebrovascular disease. J BUON. 2008 Jan-Mar;13(1):31-6. Review. PubMed PMID: 18404783.

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