112093-28-4
Chemical Structure
Endoxifen (Z-isomer)
- CAS No.: 112093-28-4
- Formula:C25H27NO2
- Molecular Weight:373.49
IUPAC Name: (Z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol
InChIKey: MHJBZVSGOZTKRH-IZHYLOQSSA-N
SMILES: OC1=CC=C(/C(C2=CC=C(OCCNC)C=C2)=C(C3=CC=CC=C3)\CC)C=C1
Biological Activity: Endoxifen Z-isomer is an orally active selective PKCβ1 inhibitor with an IC50 of 360 nM against human PKCβ1. Endoxifen Z-isomer also acts as an estrogen receptor modulator and antiestrogen. Endoxifen Z-isomer binds to and blocks ERα, ERβ and PKCβ1, inhibits estrogen and PI3K/AKT/mTORC1 signaling pathways, suppresses the expression of genes associated with cell cycle, cell proliferation and extracellular matrix remodeling, and induces apoptosis, reactive oxygen species (ROS) production and hypoxic features. Endoxifen Z-isomer inhibits tumor growth in breast tumor and glioblastoma models, reduces bone turnover and blood lipid levels, and does not require metabolism via CYP2D6. Endoxifen Z-isomer can be used in research related to ER+ breast cancer, invasive breast cancer, glioblastoma multiforme, type I bipolar disorder, desmoid tumor, gynecological malignancies, melanoma and hormone receptor-positive solid tumors[1][2][3][4][5][6][7][8][9][10].
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Endoxifen (Z-isomer) | 99.19% | Endoxifen Z-isomer is an orally active selective PKCβ1 inhibitor with an IC50 of 360 nM against human PKCβ1. Endoxifen Z-isomer also acts as an estrogen receptor modulator and antiestrogen. Endoxifen Z-isomer binds to and blocks ERα, ERβ and PKCβ1, inhibits estrogen and PI3K/AKT/mTORC1 signaling pathways, suppresses the expression of genes associated with cell cycle, cell proliferation and extracellular matrix remodeling, and induces apoptosis, reactive oxygen species (ROS) production and hypoxic features. Endoxifen Z-isomer inhibits tumor growth in breast tumor and glioblastoma models, reduces bone turnover and blood lipid levels, and does not require metabolism via CYP2D6. Endoxifen Z-isomer can be used in research related to ER+ breast cancer, invasive breast cancer, glioblastoma multiforme, type I bipolar disorder, desmoid tumor, gynecological malignancies, melanoma and hormone receptor-positive solid tumors. | ||||||||||||||||||||
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- [1]. Elkins P, et al. Characterization of the isomeric configuration and impurities of (Z)-endoxifen by 2D NMR, high resolution LC⬜MS, and quantitative HPLC analysis. Journal of pharmaceutical and biomedical analysis. 2014 Jan;88:174-9. [Content Brief]
- [2]. Lee O, et al. Z-Endoxifen prevents aggressive mammary cancers in mice by inhibiting cell proliferation and creating a tumor suppressive microenvironment. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Jun;162:114607. [Content Brief]
- [3]. Jayaraman S, et al. Endoxifen, an Estrogen Receptor Targeted Therapy: From Bench to Bedside. Endocrinology. 2021 Dec 01;162(12):bqab191. [Content Brief]
- [4]. Shneyderman A, et al. Evaluation of (Z)-endoxifen as a potential therapy for glioblastoma multiforme through computational and experimental analyses. Scientific reports. 2025 Oct 31;15(1):38225. [Content Brief]
- [5]. Nardin JM, et al. The Influences of Adherence to Tamoxifen and CYP2D6 Pharmacogenetics on Plasma Concentrations of the Active Metabolite (Z)-Endoxifen in Breast Cancer. Clinical and translational science. 2020 Mar;13(2):284-292. [Content Brief]
- [6]. Jayaraman S, et al. Antitumor activity of Z-endoxifen in aromatase inhibitor-sensitive and aromatase inhibitor-resistant estrogen receptor-positive breast cancer. Breast cancer research : BCR. 2020 May 19;22(1):51. [Content Brief]
- [7]. Jayaraman S, et al. Endoxifen downregulates AKT phosphorylation through protein kinase C beta 1 inhibition in ERα+ breast cancer. NPJ breast cancer. 2023 Dec 19;9(1):101. [Content Brief]
- [8]. Sanchez-Spitman AB, et al. Clinical pharmacokinetics and pharmacogenetics of tamoxifen and endoxifen. Expert review of clinical pharmacology. 2019 Jun;12(6):523-536. [Content Brief]
- [9]. Goetz MP, et al. First-in-Human Phase I Study of the Tamoxifen Metabolite Z-Endoxifen in Women With Endocrine-Refractory Metastatic Breast Cancer. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2017 Oct 20;35(30):3391-3400. [Content Brief]
- [10]. Takebe N, et al. Phase 1 study of Z-endoxifen in patients with advanced gynecologic, desmoid, and hormone receptor-positive solid tumors. Oncotarget. 2021 Feb 16;12(4):268-277. [Content Brief]
Keywords
