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Details

Stereochemistry ACHIRAL
Molecular Formula C28H29NO4S.ClH
Molecular Weight 512.06
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARZOXIFENE HYDROCHLORIDE

SMILES

Cl.COC1=CC=C(C=C1)C2=C(OC3=CC=C(OCCN4CCCCC4)C=C3)C5=C(S2)C=C(O)C=C5

InChI

InChIKey=NHSNLUIMAQQXGR-UHFFFAOYSA-N
InChI=1S/C28H29NO4S.ClH/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;1H

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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Unknown
149124
PubMed

PubMed

TitleDatePubMed
Evidence-based guidelines for the pharmacological treatment of postmenopausal osteoporosis: a consensus document by the Belgian Bone Club.
2010-10
New selective estrogen receptor modulators (SERMs) in development.
2010-09
Treating postmenopausal osteoporosis in women at increased risk of fracture - critical appraisal of bazedoxifene: a review.
2010-08-09
Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update.
2010-08-09
Effects of arzoxifene on bone, lipid markers, and safety parameters in postmenopausal women with low bone mass.
2010-07
Lasofoxifene: Evidence of its therapeutic value in osteoporosis.
2010-06-15
Developing drugs to treat osteoporosis: lessons learned?
2010-04
Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene.
2010-02-02
Endometrial safety: a key hurdle for selective estrogen receptor modulators in development.
2010-01-29
Modulators of androgen and estrogen receptor activity.
2010
Anti-tumor effects of retinoids combined with trastuzumab or tamoxifen in breast cancer cells: induction of apoptosis by retinoid/trastuzumab combinations.
2010
Alternative strategies for the treatment of classical congenital adrenal hyperplasia: pitfalls and promises.
2010
Endometrial cancer: what is new in adjuvant and molecularly targeted therapy?
2010
The influence of P-glycoprotein expression and its inhibitors on the distribution of doxorubicin in breast tumors.
2009-10-06
Current and emerging pharmacologic therapies for the management of postmenopausal osteoporosis.
2009-10
Resistance to antiestrogen arzoxifene is mediated by overexpression of cyclin D1.
2009-09
New selective estrogen and androgen receptor modulators.
2009-07
Effects of arzoxifene on bone mineral density and endometrium in postmenopausal women with normal or low bone mass.
2009-07
Effects of celecoxib and ly117018 combination on human breast cancer cells in vitro.
2009-04-07
Emerging drugs for postmenopausal osteoporosis.
2009-03
Designing the ideal selective estrogen receptor modulator--an achievable goal?
2009-02-03
Structural modulation of oxidative metabolism in design of improved benzothiophene selective estrogen receptor modulators.
2009-01
Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis.
2009
Arzoxifene: the evidence for its development in the management of breast cancer.
2008-07-31
The rexinoid, bexarotene, prevents the development of premalignant lesions in MMTV-erbB2 mice.
2008-04-22
Selective estrogen receptor modulators: an update on recent clinical findings.
2008-03
Phase III double-blind trial of arzoxifene compared with tamoxifen for locally advanced or metastatic breast cancer.
2007-11-01
Structure-activity relationships for a family of benzothiophene selective estrogen receptor modulators including raloxifene and arzoxifene.
2007-10
Structural modulation of reactivity/activity in design of improved benzothiophene selective estrogen receptor modulators: induction of chemopreventive mechanisms.
2007-09
The future of the new selective estrogen receptor modulators.
2007-03
Update on bazedoxifene: a novel selective estrogen receptor modulator.
2007
Effect of estrogens on skin aging and the potential role of SERMs.
2007
Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development.
2007
Interactions of the human cytosolic sulfotransferases and steroid sulfatase in the metabolism of tibolone and raloxifene.
2006-12-19
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.
2006-10-01
Developments in the pharmacotherapeutic management of osteoporosis.
2006-08
Chemical modification modulates estrogenic activity, oxidative reactivity, and metabolic stability in 4'F-DMA, a new benzothiophene selective estrogen receptor modulator.
2006-06
Arzoxifene: the development and clinical outcome of an ideal SERM.
2006-03
Prevention of breast cancer using selective oestrogen receptor modulators (SERMs).
2006
Estrogen receptors as therapeutic targets in breast cancer.
2006
Emerging selective estrogen receptor modulators: special focus on effects on coronary heart disease in postmenopausal women.
2006
Effect of the selective estrogen receptor modulator arzoxifene on repopulation of hormone-responsive breast cancer xenografts between courses of chemotherapy.
2005-11-15
Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 4'-fluoro substitution prevents quinoid formation.
2005-02
Endocrine treatment options for advanced breast cancer--the role of fulvestrant.
2005-02
Endocrinology and hormone therapy in breast cancer: selective oestrogen receptor modulators and downregulators for breast cancer - have they lost their way?
2005
Selective oestrogen receptor modulators/new antioestrogens: a clinical perspective.
2004-12
Use of estrogen antagonists and aromatase inhibitors in breast cancer and hormonally sensitive tumors of the uterine body.
2004-10
Breast cancer chemoprevention phase I evaluation of biomarker modulation by arzoxifene, a third generation selective estrogen receptor modulator.
2004-08-15
Arzoxifene: a promising new selective estrogen receptor modulator for clinical chemoprevention of breast cancer.
2004-08-15
A new MCF-7 breast cancer cell line resistant to the arzoxifene metabolite desmethylarzoxifene.
2004-05-31
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:59:58 GMT 2025
Edited
by admin
on Mon Mar 31 17:59:58 GMT 2025
Record UNII
FU88PI0433
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LY-353381.HCL
Preferred Name English
ARZOXIFENE HYDROCHLORIDE
MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
ARZOXIFENE HCL
Common Name English
ARZOXIFENE HYDROCHLORIDE [MART.]
Common Name English
LY353381.HCL
Code English
2-(P-METHOXYPHENYL)-3-(P-(2-PIPERIDINOETHOXY)PHENOXY)BENZO(B)THIOPHENE-6-OL HYDROCHLORIDE
Common Name English
ARZOXIFENE HYDROCHLORIDE [MI]
Common Name English
Arzoxifene hydrochloride [WHO-DD]
Common Name English
ARZOXIFENE HYDROCHLORIDE [USAN]
Common Name English
SERM 3
Code English
2-(4-METHOXYPHENYL)-3-(4-(2-(1-PIPERIDINYL)ETHOXY)PHENOXY)BENZO(B)THIOPHENE-6-OL HYDROCHLORIDE
Systematic Name English
SERM-3
Code English
Classification Tree Code System Code
NCI_THESAURUS C1821
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
Code System Code Type Description
FDA UNII
FU88PI0433
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
PRIMARY
MERCK INDEX
m2080
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID40939527
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
PRIMARY
CAS
182133-27-3
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
PRIMARY
DRUG BANK
DBSALT002002
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
PRIMARY
USAN
KK-31
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
PRIMARY
PUBCHEM
179338
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
PRIMARY
NCI_THESAURUS
C2460
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
PRIMARY
SMS_ID
300000045508
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
PRIMARY
ChEMBL
CHEMBL226267
Created by admin on Mon Mar 31 17:59:58 GMT 2025 , Edited by admin on Mon Mar 31 17:59:58 GMT 2025
PRIMARY
Related Record Type Details
Structure of ARZOXIFENE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ARZOXIFENE
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