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Details

Stereochemistry ACHIRAL
Molecular Formula C28H29NO4S.ClH
Molecular Weight 512.06
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARZOXIFENE HYDROCHLORIDE

SMILES

Cl.COC1=CC=C(C=C1)C2=C(OC3=CC=C(OCCN4CCCCC4)C=C3)C5=CC=C(O)C=C5S2

InChI

InChIKey=NHSNLUIMAQQXGR-UHFFFAOYSA-N
InChI=1S/C28H29NO4S.ClH/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;1H

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

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

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Breast cancer chemoprevention phase I evaluation of biomarker modulation by arzoxifene, a third generation selective estrogen receptor modulator.
2004 Aug 15
Arzoxifene: a promising new selective estrogen receptor modulator for clinical chemoprevention of breast cancer.
2004 Aug 15
Selective oestrogen receptor modulators/new antioestrogens: a clinical perspective.
2004 Dec
A new MCF-7 breast cancer cell line resistant to the arzoxifene metabolite desmethylarzoxifene.
2004 May 31
Use of estrogen antagonists and aromatase inhibitors in breast cancer and hormonally sensitive tumors of the uterine body.
2004 Oct
Endocrinology and hormone therapy in breast cancer: selective oestrogen receptor modulators and downregulators for breast cancer - have they lost their way?
2005
Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 4'-fluoro substitution prevents quinoid formation.
2005 Feb
Endocrine treatment options for advanced breast cancer--the role of fulvestrant.
2005 Feb
Effect of the selective estrogen receptor modulator arzoxifene on repopulation of hormone-responsive breast cancer xenografts between courses of chemotherapy.
2005 Nov 15
Prevention of breast cancer using selective oestrogen receptor modulators (SERMs).
2006
Estrogen receptors as therapeutic targets in breast cancer.
2006
Emerging selective estrogen receptor modulators: special focus on effects on coronary heart disease in postmenopausal women.
2006
Developments in the pharmacotherapeutic management of osteoporosis.
2006 Aug
Chemical modification modulates estrogenic activity, oxidative reactivity, and metabolic stability in 4'F-DMA, a new benzothiophene selective estrogen receptor modulator.
2006 Jun
Arzoxifene: the development and clinical outcome of an ideal SERM.
2006 Mar
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
Update on bazedoxifene: a novel selective estrogen receptor modulator.
2007
Effect of estrogens on skin aging and the potential role of SERMs.
2007
Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development.
2007
The future of the new selective estrogen receptor modulators.
2007 Mar
Phase III double-blind trial of arzoxifene compared with tamoxifen for locally advanced or metastatic breast cancer.
2007 Nov 1
Interactions of the human cytosolic sulfotransferases and steroid sulfatase in the metabolism of tibolone and raloxifene.
2007 Nov-Dec
Structure-activity relationships for a family of benzothiophene selective estrogen receptor modulators including raloxifene and arzoxifene.
2007 Oct
Structural modulation of reactivity/activity in design of improved benzothiophene selective estrogen receptor modulators: induction of chemopreventive mechanisms.
2007 Sep
The rexinoid, bexarotene, prevents the development of premalignant lesions in MMTV-erbB2 mice.
2008 Apr 22
Arzoxifene: the evidence for its development in the management of breast cancer.
2008 Jul 31
Selective estrogen receptor modulators: an update on recent clinical findings.
2008 Mar
Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis.
2009
Effects of celecoxib and ly117018 combination on human breast cancer cells in vitro.
2009 Apr 7
Structural modulation of oxidative metabolism in design of improved benzothiophene selective estrogen receptor modulators.
2009 Jan
New selective estrogen and androgen receptor modulators.
2009 Jul
Effects of arzoxifene on bone mineral density and endometrium in postmenopausal women with normal or low bone mass.
2009 Jul
Emerging drugs for postmenopausal osteoporosis.
2009 Mar
Designing the ideal selective estrogen receptor modulator--an achievable goal?
2009 May-Jun
Current and emerging pharmacologic therapies for the management of postmenopausal osteoporosis.
2009 Oct
The influence of P-glycoprotein expression and its inhibitors on the distribution of doxorubicin in breast tumors.
2009 Oct 6
Resistance to antiestrogen arzoxifene is mediated by overexpression of cyclin D1.
2009 Sep
Modulators of androgen and estrogen receptor activity.
2010
Anti-tumor effects of retinoids combined with trastuzumab or tamoxifen in breast cancer cells: induction of apoptosis by retinoid/trastuzumab combinations.
2010
Alternative strategies for the treatment of classical congenital adrenal hyperplasia: pitfalls and promises.
2010
Endometrial cancer: what is new in adjuvant and molecularly targeted therapy?
2010
Developing drugs to treat osteoporosis: lessons learned?
2010 Apr
Treating postmenopausal osteoporosis in women at increased risk of fracture - critical appraisal of bazedoxifene: a review.
2010 Aug 9
Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update.
2010 Aug 9
Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene.
2010 Feb 2
Effects of arzoxifene on bone, lipid markers, and safety parameters in postmenopausal women with low bone mass.
2010 Jul
Lasofoxifene: Evidence of its therapeutic value in osteoporosis.
2010 Jun 15
Endometrial safety: a key hurdle for selective estrogen receptor modulators in development.
2010 May-Jun
Evidence-based guidelines for the pharmacological treatment of postmenopausal osteoporosis: a consensus document by the Belgian Bone Club.
2010 Oct
New selective estrogen receptor modulators (SERMs) in development.
2010 Sep
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:31:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:31:30 GMT 2023
Record UNII
FU88PI0433
Record Status Validated (UNII)
Record Version
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Name Type Language
ARZOXIFENE HYDROCHLORIDE
MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
ARZOXIFENE HCL
Common Name English
ARZOXIFENE HYDROCHLORIDE [MART.]
Common Name English
LY353381.HCL
Code English
2-(P-METHOXYPHENYL)-3-(P-(2-PIPERIDINOETHOXY)PHENOXY)BENZO(B)THIOPHENE-6-OL HYDROCHLORIDE
Common Name English
LY-353381.HCL
Code English
ARZOXIFENE HYDROCHLORIDE [MI]
Common Name English
Arzoxifene hydrochloride [WHO-DD]
Common Name English
ARZOXIFENE HYDROCHLORIDE [USAN]
Common Name English
SERM 3
Code English
2-(4-METHOXYPHENYL)-3-(4-(2-(1-PIPERIDINYL)ETHOXY)PHENOXY)BENZO(B)THIOPHENE-6-OL HYDROCHLORIDE
Systematic Name English
SERM-3
Code English
Classification Tree Code System Code
NCI_THESAURUS C1821
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
Code System Code Type Description
FDA UNII
FU88PI0433
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
PRIMARY
MERCK INDEX
m2080
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID40939527
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
PRIMARY
CAS
182133-27-3
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
PRIMARY
DRUG BANK
DBSALT002002
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
PRIMARY
USAN
KK-31
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
PRIMARY
PUBCHEM
179338
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
PRIMARY
NCI_THESAURUS
C2460
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
PRIMARY
SMS_ID
300000045508
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL226267
Created by admin on Fri Dec 15 15:31:30 GMT 2023 , Edited by admin on Fri Dec 15 15:31:30 GMT 2023
PRIMARY
Related Record Type Details
Structure of ARZOXIFENE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ARZOXIFENE
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