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SML2368

Sigma-Aldrich

(Z)-Endoxifen

≥98% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C25H27NO2
CAS-Nummer:
112093-28-4
Molekulargewicht:
373.49
MDL-Nummer:
MFCD09840374
UNSPSC-Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 2 mg/mL, clear

Lagertemp.

2-8°C

Anwendung

(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. Wirkung

(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.

Piktogramme

Health hazardEnvironment
GHS08,GHS09

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Tamoxifen analytical standard

Supelco

85256

Tamoxifen

4-Hydroxytamoxifen gebrauchsfertige Lösung 5 mg/mL in ethanol: isopropanol (95:5)

Sigma-Aldrich

SML1666

4-Hydroxytamoxifen gebrauchsfertige Lösung

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

Supelco

06734

Tamoxifen

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
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
Matthew P Goetz et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 35(30), 3391-3400 (2017-08-31)
Purpose Endoxifen is a tamoxifen metabolite with potent antiestrogenic activity. Patients and Methods We performed a phase I study of oral Z-endoxifen to determine its toxicities, maximum tolerated dose (MTD), pharmacokinetics, and clinical activity. Eligibility included endocrine-refractory, estrogen receptor-positive metastatic
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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