E8284

(E/Z)-Endoxifen Hydrochloride Hydrate

≥98% (HPLC)

• Synonym(s): (E/Z)-Endoxifen hydrochloride hydrate, (E/Z)-4-Hydroxy-N-desmethyltamoxifen hydrochloride hydrate, (E/Z)-4-[1-[4-[2-(Methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol hydrochloride hydrate (1:1 E/Z mixture); (E/Z)-4OHNDtam hydrochloride hydrate
• Empirical Formula (Hill Notation): C₂₅H₂₇NO₂ · HCl · xH₂O
• Molecular Weight: 409.95 (anhydrous basis)
• MDL number: MFCD16875406
• UNSPSC Code: 12352203
• PubChem Substance ID: 329799077
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: solid
• storage condition: desiccated
• color: white to beige
• solubility: DMSO: >10 mg/mL
• storage temp.: 2-8°C
• SMILES string: O.Cl.CC\C(c1ccccc1)=C(/c2ccc(O)cc2)c3ccc(OCCNC)cc3
• InChI: 1S/C25H27NO2.ClH.H2O/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;1H2/b25-24-;;
• InChI key: BISAMGUAXFFKDX-NDIQBZANSA-N

Description

Application

(E/Z)-Endoxifen Hydrochloride Hydrate has been used:
as a selective estrogen receptor modulator (SERM) to study the role of miR-27a expression[1]
to impregnate a biocompatible polymer in the subcutaneous space adjacent to the TA muscle of PDGFRαCreER;R26NG mice[2]
to study its in vivo performance and properties for CreERT2 (mutant estrogen receptor) control[3]

Biochem/physiol Actions

(E/Z)-Endoxifen hydrochloride ((E/Z)-4-Hydroxy-N-desmethyltamoxifen hydrochloride) is a tamoxifen metabolite and potent Selective Estrogen Response Modifier (SERM). It is equipotent to 4-hydroxytamoxifen with respect to estrogen receptor binding and inhibition of 17-estradiol (E2)-induced cell proliferation. It is primarily catalyzed by cytochrome P450 2D6 (CYP2D6). Mutations in CYP2D6 may prevent response to tamoxifen by preventing formation of endoxifen. The gene expression patterns of five genes have been validated to be differentially regulated by endoxifen and 4-OH-Tamoxifen. Endoxifen and 4-OH-Tam have similar effects on global gene expression patterns in MCF-7 cells and the majority of the affected genes are estrogen-regulated genes.

(E/Z)-endoxifen hydrochloride may be used in hormone therapy to fight breast cancer.[4] Endoxifen is considered as an active metabolite of tamoxifen.[1] Hence it is responsible for the tamoxifen activity in the human body.[4]

Tamoxifen metabolite; Selective Estrogen response modifier (SERM) .

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: nwg
• flash_point_f: Not applicable
• flash_point_c: Not applicable