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=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

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
Breast cancer chemoprevention: beyond tamoxifen.	2001	11250754
Selective estrogen receptor modulators for the chemoprevention of prostate cancer.	2001 Apr	11295598
Endocrine manipulation in advanced breast cancer: recent advances with SERM therapies.	2001 Dec	11916228
Long-term dosing of arzoxifene lowers cholesterol, reduces bone turnover, and preserves bone quality in ovariectomized rats.	2002 Dec	12469920
Selective estrogen receptor modulators: tissue actions and potential for CNS protection.	2002 Fall	12353060
Novel therapeutic options for osteoporosis.	2002 Jul	12118183
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
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	14559845
Arzoxifene: a promising new selective estrogen receptor modulator for clinical chemoprevention of breast cancer.	2004 Aug 15	15328166
A new MCF-7 breast cancer cell line resistant to the arzoxifene metabolite desmethylarzoxifene.	2004 May 31	15196704
Endocrinology and hormone therapy in breast cancer: selective oestrogen receptor modulators and downregulators for breast cancer - have they lost their way?	2005	15987442
Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 4'-fluoro substitution prevents quinoid formation.	2005 Feb	15720120
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
Developments in the pharmacotherapeutic management of osteoporosis.	2006 Aug	16872263
Chemical modification modulates estrogenic activity, oxidative reactivity, and metabolic stability in 4'F-DMA, a new benzothiophene selective estrogen receptor modulator.	2006 Jun	16780356
Arzoxifene: the development and clinical outcome of an ideal SERM.	2006 Mar	16503767
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
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
The future of the new selective estrogen receptor modulators.	2007 Mar	17448265
Arzoxifene: the evidence for its development in the management of breast cancer.	2008 Jul 31	21221190
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
New selective estrogen and androgen receptor modulators.	2009 Jul	19412100
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
Resistance to antiestrogen arzoxifene is mediated by overexpression of cyclin D1.	2009 Sep	19477949
Modulators of androgen and estrogen receptor activity.	2010	21395502
Developing drugs to treat osteoporosis: lessons learned?	2010 Apr	20113199
Treating postmenopausal osteoporosis in women at increased risk of fracture - critical appraisal of bazedoxifene: a review.	2010 Aug 9	21072279
Effects of arzoxifene on bone, lipid markers, and safety parameters in postmenopausal women with low bone mass.	2010 Jul	19798460
Lasofoxifene: Evidence of its therapeutic value in osteoporosis.	2010 Jun 15	20694069
Endometrial safety: a key hurdle for selective estrogen receptor modulators in development.	2010 May-Jun	20107426

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:37:20 GMT 2023` Edited by `admin` on `Sat Dec 16 17:37:20 GMT 2023`
Record UNII	E569WG6E60
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARZOXIFENE

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