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Details

Stereochemistry ACHIRAL
Molecular Formula C28H29NO4S
Molecular Weight 475.599
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARZOXIFENE

SMILES

COC1=CC=C(C=C1)C2=C(OC3=CC=C(OCCN4CCCCC4)C=C3)C5=CC=C(O)C=C5S2

InChI

InChIKey=MCGDSOGUHLTADD-UHFFFAOYSA-N
InChI=1S/C28H29NO4S/c1-31-22-8-5-20(6-9-22)28-27(25-14-7-21(30)19-26(25)34-28)33-24-12-10-23(11-13-24)32-18-17-29-15-3-2-4-16-29/h5-14,19,30H,2-4,15-18H2,1H3

HIDE SMILES / InChI

Molecular Formula C28H29NO4S
Molecular Weight 475.599
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Arzoxifene (LY353381) is a synthetic, nonsteroidal ligand termed selective estrogen receptor modulator. Arzoxifene has antiestrogenic effects on the breast and endometrium, but pro-estrogenic effects on bone and lipids. Arzoxifene has been studied in the treatment of various hormone-responsive neoplasms. Its development has been discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Endocrine manipulation in advanced breast cancer: recent advances with SERM therapies.
2001 Dec
Where do selective estrogen receptor modulators (SERMs) and aromatase inhibitors (AIs) now fit into breast cancer treatment algorithms?
2001 Dec
Arzoxifene, a new selective estrogen receptor modulator for chemoprevention of experimental breast cancer.
2001 Dec 1
Effects of oral estrogen, raloxifene and arzoxifene on gene expression in serotonin neurons of macaques.
2002 May
Comparison of the selective estrogen receptor modulator arzoxifene (LY353381) with tamoxifen on tumor growth and biomarker expression in an MCF-7 human breast cancer xenograft model.
2003 Oct 1
Models of breast cancer: is merging human and animal models the future?
2004
The effect of the new SERM arzoxifene on growth and gene expression in MCF-7 breast cancer cells.
2004 Apr 30
Arzoxifene: a promising new selective estrogen receptor modulator for clinical chemoprevention of breast cancer.
2004 Aug 15
A new MCF-7 breast cancer cell line resistant to the arzoxifene metabolite desmethylarzoxifene.
2004 May 31
Prevention of breast cancer using selective oestrogen receptor modulators (SERMs).
2006
Estrogen receptors as therapeutic targets in breast cancer.
2006
Developments in the pharmacotherapeutic management of osteoporosis.
2006 Aug
Chemical modification modulates estrogenic activity, oxidative reactivity, and metabolic stability in 4'F-DMA, a new benzothiophene selective estrogen receptor modulator.
2006 Jun
The combination of the rexinoid, LG100268, and a selective estrogen receptor modulator, either arzoxifene or acolbifene, synergizes in the prevention and treatment of mammary tumors in an estrogen receptor-negative model of breast cancer.
2006 Oct 1
Structure-activity relationships for a family of benzothiophene selective estrogen receptor modulators including raloxifene and arzoxifene.
2007 Oct
Arzoxifene: the evidence for its development in the management of breast cancer.
2008 Jul 31
Selective estrogen receptor modulators: an update on recent clinical findings.
2008 Mar
Effects of celecoxib and ly117018 combination on human breast cancer cells in vitro.
2009 Apr 7
New selective estrogen and androgen receptor modulators.
2009 Jul
Effects of arzoxifene on bone mineral density and endometrium in postmenopausal women with normal or low bone mass.
2009 Jul
Resistance to antiestrogen arzoxifene is mediated by overexpression of cyclin D1.
2009 Sep
Modulators of androgen and estrogen receptor activity.
2010
Endometrial cancer: what is new in adjuvant and molecularly targeted therapy?
2010
Developing drugs to treat osteoporosis: lessons learned?
2010 Apr
Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update.
2010 Aug 9
Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene.
2010 Feb 2
Effects of arzoxifene on bone, lipid markers, and safety parameters in postmenopausal women with low bone mass.
2010 Jul
Evidence-based guidelines for the pharmacological treatment of postmenopausal osteoporosis: a consensus document by the Belgian Bone Club.
2010 Oct
New selective estrogen receptor modulators (SERMs) in development.
2010 Sep
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:37:20 UTC 2023
Edited
by admin
on Sat Dec 16 17:37:20 UTC 2023
Record UNII
E569WG6E60
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARZOXIFENE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
arzoxifene [INN]
Common Name English
LY353381
Code English
ARZOXIFENE [MART.]
Common Name English
LY-353381
Code English
2-(4-METHOXYPHENYL)-3-(4-(2-(1-PIPERIDINYL)ETHOXY)PHENOXY)BENZO(B)THIOPHENE-6-OL
Systematic Name English
ARZOXIFENE [MI]
Common Name English
Arzoxifene [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1821
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
Code System Code Type Description
FDA UNII
E569WG6E60
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
CAS
182133-25-1
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
PUBCHEM
179337
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
INN
7791
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
EVMPD
SUB00599MIG
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
MERCK INDEX
m2080
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL226267
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
DRUG BANK
DB06249
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID10171255
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
WIKIPEDIA
ARZOXIFENE
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
SMS_ID
100000085341
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
NCI_THESAURUS
C1805
Created by admin on Sat Dec 16 17:37:20 UTC 2023 , Edited by admin on Sat Dec 16 17:37:20 UTC 2023
PRIMARY
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TARGET->DEGRADER, SELECTIVE
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Competitive binding with estrogen
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TARGET -> INHIBITOR
serm Competitive binding with estrogen
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ACTIVE MOIETY