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 phase I evaluation of biomarker modulation by arzoxifene, a third generation selective estrogen receptor modulator.	2004 Aug 15	15328178
Arzoxifene: a promising new selective estrogen receptor modulator for clinical chemoprevention of breast cancer.	2004 Aug 15	15328166
Selective oestrogen receptor modulators/new antioestrogens: a clinical perspective.	2004 Dec	15541579
A new MCF-7 breast cancer cell line resistant to the arzoxifene metabolite desmethylarzoxifene.	2004 May 31	15196704
Use of estrogen antagonists and aromatase inhibitors in breast cancer and hormonally sensitive tumors of the uterine body.	2004 Oct	15535424
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
Endocrine treatment options for advanced breast cancer--the role of fulvestrant.	2005 Feb	15691633
Effect of the selective estrogen receptor modulator arzoxifene on repopulation of hormone-responsive breast cancer xenografts between courses of chemotherapy.	2005 Nov 15	16299252
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
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
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
The future of the new selective estrogen receptor modulators.	2007 Mar	17448265
Phase III double-blind trial of arzoxifene compared with tamoxifen for locally advanced or metastatic breast cancer.	2007 Nov 1	17971595
Interactions of the human cytosolic sulfotransferases and steroid sulfatase in the metabolism of tibolone and raloxifene.	2007 Nov-Dec	17662596
Structure-activity relationships for a family of benzothiophene selective estrogen receptor modulators including raloxifene and arzoxifene.	2007 Oct	17654759
Structural modulation of reactivity/activity in design of improved benzothiophene selective estrogen receptor modulators: induction of chemopreventive mechanisms.	2007 Sep	17876041
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
Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis.	2009	19898646
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
Designing the ideal selective estrogen receptor modulator--an achievable goal?	2009 May-Jun	19182697
Current and emerging pharmacologic therapies for the management of postmenopausal osteoporosis.	2009 Oct	19857095
The influence of P-glycoprotein expression and its inhibitors on the distribution of doxorubicin in breast tumors.	2009 Oct 6	19807929
Resistance to antiestrogen arzoxifene is mediated by overexpression of cyclin D1.	2009 Sep	19477949
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
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
Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update.	2010 Aug 9	21072271
Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene.	2010 Feb 2	20169039
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
Evidence-based guidelines for the pharmacological treatment of postmenopausal osteoporosis: a consensus document by the Belgian Bone Club.	2010 Oct	20480148
New selective estrogen receptor modulators (SERMs) in development.	2010 Sep	20603714

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