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Endoxifen hydrochloride (N-desmethyl-4-hydroxytamoxifen) is an active metabolite of Tamoxifen which is a potent SERM/antiestrogen. It is also being evaluated as an antipsychotic for treatment of mania and other psychotic disorders. Endoxifen is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group.
| ln Vitro |
Endoxifen, a metabolite of hydroxylated tamoxifen, has an ER antagonistic potency that is around 100 times greater than tamoxifen's. In addition to its impact on transcription within the ER, it also implies that endoxifen, but not 4-hydroxytamoxifen, causes ER-alpha degradation[1]. A strong antiestrogen called endoxifen causes breast cancer cells' estrogen receptor α to break down. Endoxifen has also been demonstrated to decrease estrogen-induced breast cancer cell proliferation and block ERA transcriptional activity, even in the presence of tamoxifen, N-desmethyl-tamoxifen, and 4-hydroxytamoxifen[2]. With the exception of MDAMB-468, which shows modest inhibition at 10 μM, doxifen significantly inhibits the development of all breast cancer cell lines. For MCF7, HS 578T, and BT-549 cells, cytotoxic effects are highly noticeable at 10 μM concentration. All studied cells showed lethality at 100 μM Endoxifen concentration, but the inhibitory effects at lower doses (0.01-1 μM) are not as strong as those at 10 μM[2].
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| ln Vivo |
In female rats, oral administration of Endoxifen results in fast absorption and systemic availability. When compared to Tamoxifen, the rats administered with Endoxifen exhibit 1,500% greater concentration (Cmax) and 787% higher exposure (AUC0–∞) levels of Endoxifen. Endoxifen given orally once daily for 28 days in a succession at doses of 2, 4, and 8 mg/kg has been shown to be safe and to gradually reduce the growth of human mammary tumor xenografts in female mice[2].
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| References |
[1]. Goetz MP, et al. Tamoxifen, endoxifen, and CYP2D6: the rules for evaluating a predictive factor. Oncology (Williston Park). 2009 Dec;23(14):1233-4, 1236.
[2]. Wu X, et al. The tamoxifen metabolite, Endoxifen, is a potent antiestrogen that targets estrogen receptor alpha fordegradation in breast cancer cells. Cancer Res. 2009 Mar 1;69(5):1722-7 |
| Additional Infomation |
Endoxifen Hydrochloride is the hydrochloride salt and the z (cis-) stereoisomer of endoxifen with potential antineoplastic activity. Endoxifen, the active metabolite of tamoxifen, competitively inhibits the binding of estradiol to estrogen receptors, thereby preventing the receptor from binding to the estrogen-response element on DNA and thus reducing DNA synthesis. Unlike tamoxifen, however, which relies on CYP2D6 activity for its conversion to the active metabolite endoxifen, the direct administration of endoxifen bypasses the CYP2D6 route. As CYP2D6 activity can vary widely among individuals due to genetic CYP2D6 polymorphisms, endoxifen is therefore theoretically more potent and more uniform in its bioavailability across patient populations.
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| Molecular Formula |
C₂₅H₂₈CLNO₂
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|---|---|
| Molecular Weight |
409.95
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| Exact Mass |
409.18
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| CAS # |
1197194-41-4
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| Related CAS # |
Endoxifen (Z-isomer);112093-28-4;Endoxifen Z-isomer hydrochloride;1032008-74-4;Endoxifen (E-isomer);114828-90-9;Endoxifen;110025-28-0;Endoxifen E-isomer hydrochloride;1197194-61-8
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| PubChem CID |
54613017
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| Appearance |
Light brown to brown solid powder
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
29
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| Complexity |
467
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| Defined Atom Stereocenter Count |
0
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| SMILES |
Cl[H].O(C([H])([H])C([H])([H])N([H])C([H])([H])[H])C1C([H])=C([H])C(=C([H])C=1[H])/C(/C1C([H])=C([H])C(=C([H])C=1[H])O[H])=C(\C1C([H])=C([H])C([H])=C([H])C=1[H])/C([H])([H])C([H])([H])[H]
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| InChi Key |
RPFIMPDXTABYCN-BJFQDICYSA-N
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| InChi Code |
InChI=1S/C25H27NO2.ClH/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(27)14-10-20)21-11-15-23(16-12-21)28-18-17-26-2;/h4-16,26-27H,3,17-18H2,1-2H3;1H/b25-24-;
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| Chemical Name |
4-[(Z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol;hydrochloride
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 35 mg/mL (~85.38 mM)
H2O : ~1 mg/mL (~2.44 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.10 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.10 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4393 mL | 12.1966 mL | 24.3932 mL | |
| 5 mM | 0.4879 mL | 2.4393 mL | 4.8786 mL | |
| 10 mM | 0.2439 mL | 1.2197 mL | 2.4393 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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