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CN

SML2368

(Z)-Endoxifen

≥98% (HPLC), selective estrogen receptor modulator, powder

Synonym(s):

4-Hydroxy-N-desmethyl-tamoxifen, Endoxifen, Metabolite BX, N-Desmethyl-4-hydroxytamoxifen, Z-Endoxifen

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About This Item

Empirical Formula (Hill Notation):
C25H27NO2
CAS Number:
112093-28-4
Molecular Weight:
373.49
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD09840374

Key Documents

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Product Name

(Z)-Endoxifen, ≥98% (HPLC)

SMILES string

N(CCOc1ccc(cc1)\C(=C(\CC)/c3ccccc3)\c2ccc(cc2)O)C

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-

InChI key

MHJBZVSGOZTKRH-IZHYLOQSSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Related Categories

Application

(Z)-Endoxifen has been used to demonstrate the lack of contribution of subventricular zone and leptomeningeal cells in a study determining the generation of neuroblasts from astrocytes.

Biochem/physiol Actions

(Z)-Endoxifen (endoxifen) is an active tamoxifen metabolite generated via actions of cytochrome P450 (CYP) enzymes CYP3A4/5 and CYP2D6. Endoxifen is more potent than tamoxifen as a selective estrogen receptor modulator (SERM) both in vitro and in vivo with good pharmacokinetics and oral availability (∼80% MCF-7 tumor growth inhibition with 4-8 mg/kg/day endoxifen or 20 mg/kg/day tamoxifen in mice via p.o.). Endoxifen also exhibits 4-fold higher PKC inhibitory potency than tamoxifen and can overcome tamoxifen resistance due to cytochrome CYP2D6 polymorphism.
Orally available, active tamoxifen metabolite with higher estrogen receptor modulator (SERM) activity and anticancer efficacy both in vitro and in vivo.

pictograms

Health hazardEnvironment
GHS08,GHS09

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000507538
0000507538
0000487463
0000487463
0000469590

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Vered Stearns et al.
Journal of the National Cancer Institute, 95(23), 1758-1764 (2003-12-05)
Tamoxifen, a selective estrogen receptor modulator (SERM), is converted to 4-hydroxy-tamoxifen and other active metabolites by cytochrome P450 (CYP) enzymes. Selective serotonin reuptake inhibitors (SSRIs), which are often prescribed to alleviate tamoxifen-associated hot flashes, can inhibit CYPs. In a prospective
Paul Chen et al.
Cellular & molecular biology letters, 23, 3-3 (2018-01-09)
Endoxifen, an active metabolite of tamoxifen, has been shown to be an effective anti-estrogenic agent in estrogen receptor-positive breast cancer patients. In melanoma, estrogen receptor expression is shown to be associated with disease progression. However, the therapeutic benefit of endoxifen
Phyllis Elkins et al.
Journal of pharmaceutical and biomedical analysis, 88, 174-179 (2013-09-24)
(Z)-Endoxifen (4-hydroxy-N-desmethyltamoxifen), an active metabolite generated via actions of CYP3A4/5 and CYP2D6, is a more potent selective estrogen receptor modulator (SERM) than tamoxifen. In the MCF-7 human mammary tumor xenograft model with female athymic mice, (Z)-endoxifen, at an oral dose
Shagufta et al.
European journal of medicinal chemistry, 143, 515-531 (2017-12-06)
Tamoxifen (ICI 46 474), trans-1-(4-β-dimethylaminoethoxyphenyl)-1,2-diphenylbut-1-ene, is the most commonly used drug for the treatment of estrogen receptor positive breast cancer and has been saving lives worldwide for the past four decades. Tamoxifen is considered a pioneering drug due to its ubiquitous
Todd C Skaar et al.
Clinical pharmacology and therapeutics, 103(5), 755-757 (2018-02-24)
This issue of Clinical Pharmacology & Therapeutics (CPT) includes the Clinical Pharmacogenetics Implementation Consortium (CPIC) guideline for using CYP2D6 genotyping to guide tamoxifen therapy for breast cancer patients. CYP2D6 metabolizes tamoxifen to its more active metabolite, endoxifen, and patients with
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