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E8284 Sigma-Aldrich

(E/Z)-Endoxifen Hydrochloride Hydrate

≥98% (HPLC)

Synonym: (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, (E/Z)-Endoxifen hydrochloride hydrate

  • Empirical Formula (Hill Notation) C25H27NO2 · HCl · xH2O

  • Molecular Weight 409.95 (anhydrous basis)

  •  MDL number MFCD16875406

  •  PubChem Substance ID 329799077

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, E
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
to impregnate a biocompatible polymer in the subcutaneous space adjacent to the TA muscle of PDGFRαCreER;R26NG mice
to study its in vivo performance and properties for CreERT2 (mutant estrogen receptor) control

Packaging

5, 25 mg in glass bottle

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. Endoxifen is considered as an active metabolite of tamoxifen. Hence it is responsible for the tamoxifen activity in the human body.

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 & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
nwg
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Nuclear Receptors (Steroids)

Intracellular receptors (IRs) are a class of ligand-dependent transcription factors that include receptors for both steroid and non-steroid hormones. Upon binding their cognate hormone, these recepto...
Keywords: Anti-inflammatory agents, Apoptosis, Atomic absorption spectroscopy, Cancer, Cardiovascular, Cell proliferation, Diseases, Diuretics, Gene expression, Hormones, Infrared spectroscopy, Ligands, Metabolism, Metabolites, Transcription, Transduction

Peer-Reviewed Papers
15

References

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