1584173-54-5
Chemical Structure
Endoxifen-d5 (Z-isomer)
- CAS No.: 1584173-54-5
- Formula:C25H22D5NO2
- Molecular Weight:378.52
IUPAC Name: (Z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl-3,3,4,4,4-d5)phenol
InChIKey: MHJBZVSGOZTKRH-JZSWEIPSSA-N
SMILES: [2H]C([2H])([2H])C([2H])([2H])/C(C1=CC=CC=C1)=C(C2=CC=C(C=C2)O)/C3=CC=C(C=C3)OCCNC
Biological Activity: Endoxifen-d5 (Z-isomer) is the deuterated-labeled Endoxifen (Z-isomer methanesulfonate) (HY-18719H). Endoxifen-d5 Z-isomer is an orally active selective PKCβ1 inhibitor with an IC50 of 360 nM against human PKCβ1. It also acts as an estrogen receptor modulator and antiestrogen. Endoxifen-d5 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-d5 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. It 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-d5 (Z-isomer) | Endoxifen-d5 (Z-isomer) is the deuterated-labeled Endoxifen (Z-isomer methanesulfonate) (HY-18719H). Endoxifen-d5 Z-isomer is an orally active selective PKCβ1 inhibitor with an IC50 of 360 nM against human PKCβ1. It also acts as an estrogen receptor modulator and antiestrogen. Endoxifen-d5 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-d5 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. It 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
