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
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
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
Arzoxifene as therapy for endometrial cancer.	2003 Aug	12928005
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
Selective estrogen receptor modulators as inhibitors of repopulation of human breast cancer cell lines after chemotherapy.	2003 Oct 1	14555537
Arzoxifene Eli Lilly.	2003 Sep	12964068
Randomized, double-blind, multicenter trial comparing two doses of arzoxifene (LY353381) in hormone-sensitive advanced or metastatic breast cancer patients.	2003 Sep	12954577
Models of breast cancer: is merging human and animal models the future?	2004	14680482
The effect of the new SERM arzoxifene on growth and gene expression in MCF-7 breast cancer cells.	2004 Apr 30	15149724
The use of selective estrogen receptor modulators and selective estrogen receptor down-regulators in breast cancer.	2004 Mar	14687597
The selective estrogen receptor modulator arzoxifene and the rexinoid LG100268 cooperate to promote transforming growth factor beta-dependent apoptosis in breast cancer.	2004 May 15	15150113
Prevention of breast cancer using selective oestrogen receptor modulators (SERMs).	2006	17049068
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
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
New selective estrogen and androgen receptor modulators.	2009 Jul	19412100
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
Resistance to antiestrogen arzoxifene is mediated by overexpression of cyclin D1.	2009 Sep	19477949
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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:37:20 UTC 2023` Edited by `admin` on `Sat Dec 16 17:37:20 UTC 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