CAS 112093-28-4|Endoxifen (Z-isomer)

Introduction：Basic information about CAS 112093-28-4|Endoxifen (Z-isomer), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Endoxifen (Z-isomer) BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Synonyms

Common Name	Endoxifen (Z-isomer)
CAS Number	112093-28-4	Molecular Weight	373.48700
Density	1.099g/cm3	Boiling Point	519.327ºC at 760 mmHg
Molecular Formula	C₂₅H₂₇NO₂	Melting Point	127-129°C
MSDS	USA	Flash Point	267.88ºC
Symbol	GHS09	Signal Word	Warning

Names

Name	4-[(Z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
Synonym	More Synonyms

Endoxifen (Z-isomer) BiologicalActivity

Description	Endoxifen Z-isomer is the most important Tamoxifen metabolite responsible for eliciting the anti-estrogenic effects of this drug in breast cancer cells expressing estrogen receptor-alpha (ERα). Endoxifen inhibits hERG tail currents at 50 mV in a concentration-dependent manner with IC50 values of 1.6 μM.IC50 value: 1.6 μM [1]Target: hERG Potassium Channel, Estrogen Receptor/ERREndoxifen Z-isomer is considered a prodrug, since it has a much higher potency for the estrogen receptor than its parent drug. Endoxifen inhibits the hERG channel protein trafficking to the plasma membrane in a concentration-dependent manner with Endoxifen being more potent than Tamoxifen. [1] Endoxifen is also shown to be a more potent inhibitor of estrogen target genes when ERβ is expressed. Additionally, low concentrations of Endoxifen Z-isomer observed in Tamoxifen treated patients with deficient CYP2D6 activity (20 to 40 nM) markedly inhibit estrogen-induced cell proliferation rates in the presence of ERβ, whereas much higher Endoxifen Z-isomer concentrations are needed when ERβ is absent.[2]
Related Catalog	Signaling Pathways >>Others >>Estrogen Receptor/ERRSignaling Pathways >>Membrane Transporter/Ion Channel >>Potassium ChannelResearch Areas >>Cancer
References	[1]. Chae YJ, et al. Endoxifen, the active metabolite of tamoxifen, inhibits cloned hERG potassium channels. Eur J Pharmacol. 2015 Apr 5;752:1-7. [2]. Wu X, et al. Estrogen receptor-beta sensitizes breast cancer cells to the anti-estrogenic actions of endoxifen. Breast Cancer Res. 2011 Mar 10;13(2):R27.

Description

Endoxifen Z-isomer is the most important Tamoxifen metabolite responsible for eliciting the anti-estrogenic effects of this drug in breast cancer cells expressing estrogen receptor-alpha (ERα). Endoxifen inhibits hERG tail currents at 50 mV in a concentration-dependent manner with IC50 values of 1.6 μM.IC50 value: 1.6 μM [1]Target: hERG Potassium Channel, Estrogen Receptor/ERREndoxifen Z-isomer is considered a prodrug, since it has a much higher potency for the estrogen receptor than its parent drug. Endoxifen inhibits the hERG channel protein trafficking to the plasma membrane in a concentration-dependent manner with Endoxifen being more potent than Tamoxifen. [1] Endoxifen is also shown to be a more potent inhibitor of estrogen target genes when ERβ is expressed. Additionally, low concentrations of Endoxifen Z-isomer observed in Tamoxifen treated patients with deficient CYP2D6 activity (20 to 40 nM) markedly inhibit estrogen-induced cell proliferation rates in the presence of ERβ, whereas much higher Endoxifen Z-isomer concentrations are needed when ERβ is absent.[2]

Related Catalog

Signaling Pathways >>Others >>Estrogen Receptor/ERRSignaling Pathways >>Membrane Transporter/Ion Channel >>Potassium ChannelResearch Areas >>Cancer

References

[1]. Chae YJ, et al. Endoxifen, the active metabolite of tamoxifen, inhibits cloned hERG potassium channels. Eur J Pharmacol. 2015 Apr 5;752:1-7.

[2]. Wu X, et al. Estrogen receptor-beta sensitizes breast cancer cells to the anti-estrogenic actions of endoxifen. Breast Cancer Res. 2011 Mar 10;13(2):R27.

Chemical & Physical Properties

Density	1.099g/cm3
Boiling Point	519.327ºC at 760 mmHg
Melting Point	127-129°C
Molecular Formula	C₂₅H₂₇NO₂
Molecular Weight	373.48700
Flash Point	267.88ºC
Exact Mass	373.20400
PSA	41.49000
LogP	5.75040
Vapour Pressure	0mmHg at 25°C
Index of Refraction	1.599
InChIKey	MHJBZVSGOZTKRH-IZHYLOQSSA-N
SMILES	CCC(=C(c1ccc(O)cc1)c1ccc(OCCNC)cc1)c1ccccc1
Storage condition	Amber Vial, -86°C Freezer, Under Inert Atmosphere

Safety Information

Symbol	GHS09
Signal Word	Warning
Hazard Statements	H400
Precautionary Statements	P273-P391
RIDADR	UN 3077 9 / PGIII
RTECS	SL8285000

Synonyms

Z-Endoxifen

4OHNDtam

4-Hydroxy-N-desmethyltamoxifen

Endoxifen

UNII-46AF8680RC

Endoxifen (Z-isomer)

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