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SML2368

Sigma-Aldrich

(Z)-Endoxifen

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :
C25H27NO2
Numéro CAS:
112093-28-4
Poids moléculaire :
373.49
Numéro MDL:
MFCD09840374
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Essai

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

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-

Clé InChI

MHJBZVSGOZTKRH-IZHYLOQSSA-N

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.

Actions biochimiques/physiologiques

(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.

Pictogrammes

Health hazardEnvironment
GHS08,GHS09

Mention d'avertissement

Danger

Mentions de danger

H350,H360,H410

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000392837
0000392839
0000369190
0000369190
0000392839

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Tamoxifène analytical standard

Supelco

85256

Tamoxifène

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

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

Supelco

06734

Tamoxifène

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
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
Leonid A Ilchuk et al.
International journal of molecular sciences, 23(22) (2022-11-27)
Inducible Cre-dependent systems are frequently used to produce both conditional knockouts and transgenic mice with regulated expression of the gene of interest. Induction can be achieved by doxycycline-dependent transcription of the wild type gene or OH-tamoxifen-dependent nuclear translocation of the
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