Endoxifen Z-isomer

• CAT Number: I000461
• CAS Number: 112093-28-4
• Molecular Formula: C25H27NO2
• Molecular Weight: 373.49
• Purity: 98%
• Synonyms: (Z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol
• Target: C5aR
• Target Protein: P21730
• Solubility: 10 mM in DMSO
• Appearance: Solid
• Storage: Dry, dark and at 2 - 8 °C for six months or -20°C for two years.
• IC50: Avacopan, a selective C5a receptor inhibitor administered orally, gained approval in 2021 for treating adults with ANCA-associated vasculitis. In the pivotal phase 3 ADVOCATE trial involving patients with active granulomatosis with polyangiitis or microscopic polyangiitis, the avacopan group exhibited superior sustained remission rates at 52 weeks compared to the prednisone group.
• IUPAC Name: 4-[(Z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
• InChI: InChI=1S/C25H27NO2/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/b25-24-
• InChIKey: MHJBZVSGOZTKRH-IZHYLOQSSA-N
• SMILES: CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCNC)/C3=CC=CC=C3

Endoxifen Z-isomer（Cat No.:I000461）is an active metabolite of tamoxifen, a selective estrogen receptor modulator (SERM) used in the treatment of estrogen receptor-positive (ER+) breast cancer. The Z-isomer form is particularly potent, directly binding to estrogen receptors and inhibiting estrogen-driven cancer cell proliferation. Endoxifen Z-isomer offers a more effective alternative to tamoxifen in patients with poor CYP2D6 metabolism, which affects the conversion of tamoxifen to endoxifen. Its direct action on estrogen receptors provides enhanced efficacy, reducing the recurrence of breast cancer and offering a personalized approach to hormone therapy.

Reference

[1]. Chae YJ, et al. Endoxifen, the active metabolite of tamoxifen, inhibits cloned hERG potassium channels. Eur J Pharmacol. 2015 Apr 5;752:1-7.
[2]. Wu X, et al. Estrogen receptor-beta sensitizes breast cancer cells to the anti-estrogenic actions of endoxifen. Breast Cancer Res. 2011 Mar 10;13(2):R27.