ENDOXIFEN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H27NO2
Molecular Weight	373.4874
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC\C(=C(/C1=CC=C(O)C=C1)C2=CC=C(OCCNC)C=C2)C3=CC=CC=C3

InChI

InChIKey=MHJBZVSGOZTKRH-IZHYLOQSSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C25H27NO2
Molecular Weight	373.4874
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23382923https://www.ncbi.nlm.nih.gov/pubmed/24055701
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27346789 https://www.ncbi.nlm.nih.gov/pubmed/21378205

(E)-Endoxifen is the E-isomer of (Z)-Endoxifen, potent selective estrogen receptor modulator. Endoxifen exists as the potently anti-estrogenic (Z)-isomer and the lesser known (E)-isomer. It is assumed that (E)-Endoxifen, structurally related to (E)-4-OH-tamoxifen, have similar pharmacological properties. The (E)-isomer is an impurity in (Z)-Endoxifen drug substance and increases under certain storage conditions. (E)-Endoxifen is identified as the primary degradant.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22277276	Modulator 828
Estrogen receptor 75 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23382923	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2578
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27438264	Primary	Phase II 1132	Unknown Approved Use Unknown
Bipolar I disorder 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27346789	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
1874 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28854070	160 mg 1 times / day steady-state, oral dose: 160 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ENDOXIFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
635 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28854070	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	ENDOXIFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
15.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20981001	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	ENDOXIFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
37.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28854070	160 mg 1 times / day steady-state, oral dose: 160 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ENDOXIFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
9.81 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28854070	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	ENDOXIFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
801 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20981001	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	ENDOXIFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
54.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28854070	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:		ENDOXIFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
52.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20981001	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		ENDOXIFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P007EKL	https://www.1pchem.com/search?query=1P007EKL
1PlusChem LLC	1P007V6I	https://www.1pchem.com/search?query=1P007V6I
1PlusChem LLC	1P008U5E	https://www.1pchem.com/search?query=1P008U5E
1PlusChem LLC	1P008U5F	https://www.1pchem.com/search?query=1P008U5F
A2B Chem	AD66202	http://a2bchem.com/prod/AD66202
AK Scientific	X5886	https://aksci.com/item_detail.php?cat=X5886
Angene	AGN-PC-0WH1I2	http://www.angenechemical.com/productshow/AGN-PC-0WH1I2.html
ApexBio Technology	B7481	https://www.apexbt.com/catalogsearch/result/?q=B7481
Axon MedChem	2190	https://www.axonmedchem.com/product/2190
Axon MedChem	2221	https://www.axonmedchem.com/product/2221
Axon MedChem	2707	https://www.axonmedchem.com/product/2707
BLD Pharm	BD765594	http://www.bldpharm.com/search/Search.html?keyword=BD765594
BOC Sciences	110025-28-0	http://www.bocsci.com/description.asp?cas=110025-28-0
BOC Sciences	112093-28-4	http://www.bocsci.com/description.asp?cas=112093-28-4
BioSynth	W-200834	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-200834
Cayman Chemical	16022	http://www.caymanchem.com/app/template/Product.vm/catalog/16022
Chem Scene	CS-5082	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5082
Chem Scene	CS-5098	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5098
Chem Scene	CS-5915	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5915
ChemShuttle	139397	https://www.chemshuttle.com/catalogsearch/result/?q=139397
ChemShuttle	186158	https://www.chemshuttle.com/catalogsearch/result/?q=186158
Enamine	EN300-822190	https://www.enaminestore.com/catalog/EN300-822190
Excenen	EX-A1970	http://www.excenen.com/searchresultlist.php?id=EX-A1970
Excenen	EX-A645	http://www.excenen.com/searchresultlist.php?id=EX-A645
Lab Network	LN01271205	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01271205
MedChem Express	HY-18719A	https://www.medchemexpress.com/search.html?q=HY-18719A&ft=&fa=&fp=
MedChem Express	HY-18719	https://www.medchemexpress.com/search.html?q=HY-18719B&ft=&fa=&fp=
MedChem Express	HY-18719B	https://www.medchemexpress.com/search.html?q=HY-18719B&ft=&fa=&fp=
MolPort	MolPort-003-846-367	https://www.molport.com/shop/molecule-link/MolPort-003-846-367
MolPort	MolPort-006-394-392	https://www.molport.com/shop/molecule-link/MolPort-006-394-392
MolPort	MolPort-039-193-827	https://www.molport.com/shop/molecule-link/MolPort-039-193-827
MolPort	MolPort-044-562-370	https://www.molport.com/shop/molecule-link/MolPort-044-562-370
MolPort	MolPort-046-418-365	https://www.molport.com/shop/molecule-link/MolPort-046-418-365
Molcore	MC34383	http://www.molcore.com/CatMC34383.html
Molnova	M17762	https://www.molnova.com/en/serch-list.html?keywords=M17762
Molnova	M17807	https://www.molnova.com/en/serch-list.html?keywords=M17807
MuseChem	I000721	https://www.musechem.com/product/I000721.html
MuseChem	I006671	https://www.musechem.com/product/I006671.html
MuseChem	R005181	https://www.musechem.com/product/R005181.html
Ryan Scientific	101-94156	https://ryansci.com/products?q=101-94156&list_q=&search_type=exact
Ryan Scientific	101-94180	https://ryansci.com/products?q=101-94180&list_q=&search_type=exact
Selleck Chemicals	S7839	http://www.selleckchem.com/search.html?searchDTO.searchParam=S7839
ShangHai Biochempartner	BCP15866	http://www.biochempartner.com/search_BCP15866
TargetMol	T2280	https://www.targetmol.com/search?keyword=T2280
TargetMol	T4281	https://www.targetmol.com/search?keyword=T4281
TargetMol	T6827	https://www.targetmol.com/search?keyword=T6827
Toronto Research Chemicals	D292043	https://www.trc-canada.com/product-detail/?CatNum=D292043
Toronto Research Chemicals	H938495	https://www.trc-canada.com/product-detail/?CatNum=H938495
Wonderchem	WD04PWB	http://www.wonder-chem.com/search.html?text=WD04PWB
eMolecules	104337173	https://orderbb.emolecules.com/search/#?query=104337173
eMolecules	104707922	https://orderbb.emolecules.com/search/#?query=104707922
eMolecules	50524303	https://orderbb.emolecules.com/search/#?query=50524303
eMolecules	55540582	https://orderbb.emolecules.com/search/#?query=55540582
eMolecules	75542257	https://orderbb.emolecules.com/search/#?query=75542257
eNovation Chemicals	D548223	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D548223&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-4095349886	https://mcule.com/MCULE-4095349886/
mcule	MCULE-5511007277	https://mcule.com/MCULE-5511007277/
mcule	MCULE-7994163547	https://mcule.com/MCULE-7994163547/
mcule	MCULE-9436224043	https://mcule.com/MCULE-9436224043/

PubMed

Title	Date	PubMed
		252160833
		252160809
Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine.	2003 Dec 3	14652237
The tamoxifen metabolite, endoxifen, is a potent antiestrogen that targets estrogen receptor alpha for degradation in breast cancer cells.	2009 Mar 1	19244106

Patents

Sample Use Guides

In Vivo Use Guide

Patients orally administered 4 mg/day or 8 mg/day endoxifen

Route of Administration: Oral

In Vitro Use Guide

The effects of tamoxifen, and its active metabolite endoxifen on hERG currents stably expressed in HEK cells were investigated using the whole-cell patch-clamp technique and an immunoblot assay. Tamoxifen and endoxifen inhibited hERG tail currents at -50mV in a concentration-dependent manner with IC50 values of 1.2 and 1.6μM, respectively. The steady-state activation curve of the hERG currents was shifted to the hyperpolarizing direction in the presence of endoxifen. The voltage-dependent inhibition of hERG currents by endoxifen increased steeply in the voltage range of channel activation.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:03:02 UTC 2023` Edited by `admin` on `Sat Dec 16 05:03:02 UTC 2023`
Record UNII	46AF8680RC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENDOXIFEN

Common Name

English

N-DESMETHYL-4-HYDROXYTAMOXIFEN

Common Name

English

NSC-749798

Code

English

Z-ENDOXIFEN

Common Name

English

Endoxifen [WHO-DD]

Common Name

English

PHENOL, 4-((1Z)-1-(4-(2-(METHYLAMINO)ETHOXY)PHENYL)-2-PHENYL-1-BUTEN-1-YL)-

Systematic Name

English

4-HYDROXY-N-DESMETHYLTAMOXIFEN

Common Name

English

Code System Code Type Description

CAS

110025-28-0