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/24055701https://www.ncbi.nlm.nih.gov/pubmed/23382923
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

Endoxifen, also known as N-desmethyl-4-hydroxytamoxifen, is active metabolites of tamoxifen. This metabolite exhibits a 100-fold higher binding affinity to the estrogen receptor (ER) and are more effective in suppressing cell proliferation than tamoxifen. In humans, the conversion from tamoxifen to endoxifen is predominant. Endoxifenis is an orally active, selective estrogen receptor modulator (SERM) that was developed for the treatment of estrogen receptor-positive breast cancer. In addition, this drug possesses antimanic properties, what can be used in the treatment of patients with bipolar I disorder (BPD I).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 134 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22277276	Modulator 846
Estrogen receptor 72 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23382923	Modulator 846

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2596
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27438264	Primary	Phase II 1147	Unknown Approved Use Unknown
Bipolar I disorder 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27346789	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
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
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://www.ncbi.nlm.nih.gov/pubmed/20981001	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	ENDOXIFEN, (E)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Analyte	Population
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
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://www.ncbi.nlm.nih.gov/pubmed/20981001	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	ENDOXIFEN, (E)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
8.46 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27346789	4 mg 1 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ENDOXIFEN, (E)- plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
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
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://www.ncbi.nlm.nih.gov/pubmed/20981001	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	ENDOXIFEN, (E)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
52.05 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27346789	4 mg 1 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ENDOXIFEN, (E)- plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

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
BioSynth	W-200834	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-200834
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
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
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
Enamine	EN300-822190	https://www.enaminestore.com/catalog/EN300-822190
eNovation Chemicals	D548223	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D548223&searchbtn.x=0&searchbtn.y=0
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
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/
MedChem Express	HY-18719	https://www.medchemexpress.com/search.html?q=HY-18719B&ft=&fa=&fp=
MedChem Express	HY-18719A	https://www.medchemexpress.com/search.html?q=HY-18719A&ft=&fa=&fp=
MedChem Express	HY-18719B	https://www.medchemexpress.com/search.html?q=HY-18719B&ft=&fa=&fp=
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
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
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

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

MCF-7 cells were treated with the test compounds ((E/Z)-Endoxifen) at the indicated concentrations in the presence or absence of 10 mkM of MG132 for 6 h, and then the cells were collected and extracted with lysis buffer (1% SDS, 0.1 M Tris–HCl (pH 7.0), 10% glycerol) and boiled for 10 min. Protein concentrations were determined by the BCA method, and equal amounts of protein lysate were separated by SDS–PAGE, transferred to a PVDF membrane, and Western blotted using the following antibodies: anti-human ERa mouse monoclonal antibody (Santa Cruz), anti-b-actin mouse monoclonal antibody (SIGMA), and anti-human cIAP1 goat polyclonal antibody (R&D systems).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:25:59 GMT 2025` Edited by `admin` on `Mon Mar 31 21:25:59 GMT 2025`
Record UNII	46AF8680RC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENDOXIFEN

Common Name

English

4-HYDROXY-N-DESMETHYLTAMOXIFEN

Preferred 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

Code System Code Type Description

CAS

110025-28-0