ARZOXIFENE

Possibly Marketed Outside US

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 Search

SMILES

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9765314 | https://www.ncbi.nlm.nih.gov/pubmed/16503767 | https://www.ncbi.nlm.nih.gov/pubmed/12964068 | https://adisinsight.springer.com/drugs/800010379

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

PubMed

Title	Date	PubMed
Evidence-based guidelines for the pharmacological treatment of postmenopausal osteoporosis: a consensus document by the Belgian Bone Club.	2010-10	20480148
New selective estrogen receptor modulators (SERMs) in development.	2010-09	20603714
Treating postmenopausal osteoporosis in women at increased risk of fracture - critical appraisal of bazedoxifene: a review.	2010-08-09	21072279
Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update.	2010-08-09	21072271
Effects of arzoxifene on bone, lipid markers, and safety parameters in postmenopausal women with low bone mass.	2010-07	19798460
Lasofoxifene: Evidence of its therapeutic value in osteoporosis.	2010-06-15	20694069
Developing drugs to treat osteoporosis: lessons learned?	2010-04	20113199
Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene.	2010-02-02	20169039
Endometrial safety: a key hurdle for selective estrogen receptor modulators in development.	2010-01-29	20107426
Modulators of androgen and estrogen receptor activity.	2010	21395502
Anti-tumor effects of retinoids combined with trastuzumab or tamoxifen in breast cancer cells: induction of apoptosis by retinoid/trastuzumab combinations.	2010	20696059
Alternative strategies for the treatment of classical congenital adrenal hyperplasia: pitfalls and promises.	2010	20652035
Endometrial cancer: what is new in adjuvant and molecularly targeted therapy?	2010	20148071
The influence of P-glycoprotein expression and its inhibitors on the distribution of doxorubicin in breast tumors.	2009-10-06	19807929
Current and emerging pharmacologic therapies for the management of postmenopausal osteoporosis.	2009-10	19857095
Resistance to antiestrogen arzoxifene is mediated by overexpression of cyclin D1.	2009-09	19477949
New selective estrogen and androgen receptor modulators.	2009-07	19412100
Effects of arzoxifene on bone mineral density and endometrium in postmenopausal women with normal or low bone mass.	2009-07	19351734
Effects of celecoxib and ly117018 combination on human breast cancer cells in vitro.	2009-04-07	21556247
Emerging drugs for postmenopausal osteoporosis.	2009-03	19249985
Designing the ideal selective estrogen receptor modulator--an achievable goal?	2009-02-03	19182697
Structural modulation of oxidative metabolism in design of improved benzothiophene selective estrogen receptor modulators.	2009-01	18936111
Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis.	2009	19898646
Arzoxifene: the evidence for its development in the management of breast cancer.	2008-07-31	21221190
The rexinoid, bexarotene, prevents the development of premalignant lesions in MMTV-erbB2 mice.	2008-04-22	18362934
Selective estrogen receptor modulators: an update on recent clinical findings.	2008-03	18279543
Phase III double-blind trial of arzoxifene compared with tamoxifen for locally advanced or metastatic breast cancer.	2007-11-01	17971595
Structure-activity relationships for a family of benzothiophene selective estrogen receptor modulators including raloxifene and arzoxifene.	2007-10	17654759
Structural modulation of reactivity/activity in design of improved benzothiophene selective estrogen receptor modulators: induction of chemopreventive mechanisms.	2007-09	17876041
The future of the new selective estrogen receptor modulators.	2007-03	17448265
Update on bazedoxifene: a novel selective estrogen receptor modulator.	2007	18044180
Effect of estrogens on skin aging and the potential role of SERMs.	2007	18044179
Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development.	2007	17503894
Interactions of the human cytosolic sulfotransferases and steroid sulfatase in the metabolism of tibolone and raloxifene.	2006-12-19	17662596
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	17020999
Developments in the pharmacotherapeutic management of osteoporosis.	2006-08	16872263
Chemical modification modulates estrogenic activity, oxidative reactivity, and metabolic stability in 4'F-DMA, a new benzothiophene selective estrogen receptor modulator.	2006-06	16780356
Arzoxifene: the development and clinical outcome of an ideal SERM.	2006-03	16503767
Prevention of breast cancer using selective oestrogen receptor modulators (SERMs).	2006	17049068
Estrogen receptors as therapeutic targets in breast cancer.	2006	16515478
Emerging selective estrogen receptor modulators: special focus on effects on coronary heart disease in postmenopausal women.	2006	16451093
Effect of the selective estrogen receptor modulator arzoxifene on repopulation of hormone-responsive breast cancer xenografts between courses of chemotherapy.	2005-11-15	16299252
Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 4'-fluoro substitution prevents quinoid formation.	2005-02	15720120
Endocrine treatment options for advanced breast cancer--the role of fulvestrant.	2005-02	15691633
Endocrinology and hormone therapy in breast cancer: selective oestrogen receptor modulators and downregulators for breast cancer - have they lost their way?	2005	15987442
Selective oestrogen receptor modulators/new antioestrogens: a clinical perspective.	2004-12	15541579
Use of estrogen antagonists and aromatase inhibitors in breast cancer and hormonally sensitive tumors of the uterine body.	2004-10	15535424
Breast cancer chemoprevention phase I evaluation of biomarker modulation by arzoxifene, a third generation selective estrogen receptor modulator.	2004-08-15	15328178
Arzoxifene: a promising new selective estrogen receptor modulator for clinical chemoprevention of breast cancer.	2004-08-15	15328166
A new MCF-7 breast cancer cell line resistant to the arzoxifene metabolite desmethylarzoxifene.	2004-05-31	15196704

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:21:13 GMT 2025` Edited by `admin` on `Wed Apr 02 09:21:13 GMT 2025`
Record UNII	E569WG6E60
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARZOXIFENE

Official Name

English

LY-353381

Preferred Name

English

arzoxifene [INN]

Common Name

English

LY353381

Code

English

ARZOXIFENE [MART.]

Common Name

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