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SML2368

Sigma-Aldrich

(Z)-Endoxifen

≥98% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C25H27NO2
Número de CAS:
112093-28-4
Peso molecular:
373.49
MDL number:
MFCD09840374
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

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.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Tamoxifeno analytical standard

Supelco

85256

Tamoxifeno

4-Hydroxytamoxifen Ready Made Solution 5 mg/mL in ethanol: isopropanol (95:5)

Sigma-Aldrich

SML1666

4-Hydroxytamoxifen Ready Made Solution

Tamoxifen citrate salt ≥99%

Sigma-Aldrich

T9262

Tamoxifen citrate salt

Tamoxifeno certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

Supelco

06734

Tamoxifeno

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
Ateeq Ahmad et al.
Breast cancer research and treatment, 122(2), 579-584 (2010-01-07)
Endoxifen is the key active metabolite of tamoxifen, a widely used breast cancer drug. Orally administered tamoxifen, is extensively metabolized by cytochrome P450 (CYP) enzymes, namely CYP3A4 and CYP2D6, into active metabolites, especially endoxifen. Due to genetic polymorphism of CYP2D6
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
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
Janina Johänning et al.
Archives of toxicology, 92(3), 1099-1112 (2017-12-30)
Tamoxifen, a standard therapy for breast cancer, is metabolized to compounds with anti-estrogenic as well as estrogen-like action at the estrogen receptor. Little is known about the formation of estrogen-like metabolites and their biological impact. Thus, we characterized the estrogen-like
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