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
Activation of a uterine insulin-like growth factor I signaling pathway by clinical and environmental estrogens: requirement of estrogen receptor-alpha.	2000 Sep	10965916
Breast cancer chemoprevention: beyond tamoxifen.	2001	11250754
Selective estrogen receptor modulators for the chemoprevention of prostate cancer.	2001 Apr	11295598
Analysis of cross-resistance of the selective estrogen receptor modulators arzoxifene (LY353381) and LY117018 in tamoxifen-stimulated breast cancer xenografts.	2001 Aug	11489833
Endocrine manipulation in advanced breast cancer: recent advances with SERM therapies.	2001 Dec	11916228
Where do selective estrogen receptor modulators (SERMs) and aromatase inhibitors (AIs) now fit into breast cancer treatment algorithms?	2001 Dec	11850229
Arzoxifene, a new selective estrogen receptor modulator for chemoprevention of experimental breast cancer.	2001 Dec 1	11731420
Selective estrogen receptor modulators: tissue actions and potential for CNS protection.	2002 Fall	12353060
Novel therapeutic options for osteoporosis.	2002 Jul	12118183
SERMs: current status and future trends.	2002 Jul	12098608
A review of selective estrogen receptor modulators in the treatment of breast and endometrial cancer.	2002 Jun	12138407
Effects of oral estrogen, raloxifene and arzoxifene on gene expression in serotonin neurons of macaques.	2002 May	11911997
Advances in breast cancer treatment and prevention: preclinical studies on aromatase inhibitors and new selective estrogen receptor modulators (SERMs).	2003	12927029
Pharmacokinetics of selective estrogen receptor modulators.	2003	12648026
Novel therapies for osteoporosis.	2003 Apr	12665416
Arzoxifene as therapy for endometrial cancer.	2003 Aug	12928005
A phase II trial of arzoxifene, a selective estrogen response modulator, in patients with recurrent or advanced endometrial cancer.	2003 Jul	12821343
Phase II, randomized, double-blind study of two dose levels of arzoxifene in patients with locally advanced or metastatic breast cancer.	2003 Mar 15	12637464
The effect of the new SERM arzoxifene on growth and gene expression in MCF-7 breast cancer cells.	2004 Apr 30	15149724
Prevention of breast cancer using selective oestrogen receptor modulators (SERMs).	2006	17049068
Developments in the pharmacotherapeutic management of osteoporosis.	2006 Aug	16872263
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	17020999
Update on bazedoxifene: a novel selective estrogen receptor modulator.	2007	18044180
Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development.	2007	17503894
Phase III double-blind trial of arzoxifene compared with tamoxifen for locally advanced or metastatic breast cancer.	2007 Nov 1	17971595
The rexinoid, bexarotene, prevents the development of premalignant lesions in MMTV-erbB2 mice.	2008 Apr 22	18362934
Arzoxifene: the evidence for its development in the management of breast cancer.	2008 Jul 31	21221190
Selective estrogen receptor modulators: an update on recent clinical findings.	2008 Mar	18279543
Effects of celecoxib and ly117018 combination on human breast cancer cells in vitro.	2009 Apr 7	21556247
Structural modulation of oxidative metabolism in design of improved benzothiophene selective estrogen receptor modulators.	2009 Jan	18936111
Effects of arzoxifene on bone mineral density and endometrium in postmenopausal women with normal or low bone mass.	2009 Jul	19351734
Emerging drugs for postmenopausal osteoporosis.	2009 Mar	19249985
Designing the ideal selective estrogen receptor modulator--an achievable goal?	2009 May-Jun	19182697
The influence of P-glycoprotein expression and its inhibitors on the distribution of doxorubicin in breast tumors.	2009 Oct 6	19807929
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
Treating postmenopausal osteoporosis in women at increased risk of fracture - critical appraisal of bazedoxifene: a review.	2010 Aug 9	21072279
Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update.	2010 Aug 9	21072271
Effects of arzoxifene on bone, lipid markers, and safety parameters in postmenopausal women with low bone mass.	2010 Jul	19798460

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