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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: beyond tamoxifen.
2001
Analysis of cross-resistance of the selective estrogen receptor modulators arzoxifene (LY353381) and LY117018 in tamoxifen-stimulated breast cancer xenografts.
2001 Aug
Where do selective estrogen receptor modulators (SERMs) and aromatase inhibitors (AIs) now fit into breast cancer treatment algorithms?
2001 Dec
Long-term dosing of arzoxifene lowers cholesterol, reduces bone turnover, and preserves bone quality in ovariectomized rats.
2002 Dec
Novel therapeutic options for osteoporosis.
2002 Jul
A review of selective estrogen receptor modulators in the treatment of breast and endometrial cancer.
2002 Jun
Arzoxifene in breast cancer.
2002 Nov
Prevention and treatment of experimental breast cancer with the combination of a new selective estrogen receptor modulator, arzoxifene, and a new rexinoid, LG 100268.
2002 Oct
Pharmacokinetics of selective estrogen receptor modulators.
2003
Arzoxifene as therapy for endometrial cancer.
2003 Aug
Phase II, randomized, double-blind study of two dose levels of arzoxifene in patients with locally advanced or metastatic breast cancer.
2003 Mar 15
Breast cancer chemoprevention phase I evaluation of biomarker modulation by arzoxifene, a third generation selective estrogen receptor modulator.
2004 Aug 15
The use of selective estrogen receptor modulators and selective estrogen receptor down-regulators in breast cancer.
2004 Mar
Endocrinology and hormone therapy in breast cancer: selective oestrogen receptor modulators and downregulators for breast cancer - have they lost their way?
2005
Effect of the selective estrogen receptor modulator arzoxifene on repopulation of hormone-responsive breast cancer xenografts between courses of chemotherapy.
2005 Nov 15
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
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
The future of the new selective estrogen receptor modulators.
2007 Mar
Structural modulation of reactivity/activity in design of improved benzothiophene selective estrogen receptor modulators: induction of chemopreventive mechanisms.
2007 Sep
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
Developing drugs to treat osteoporosis: lessons learned?
2010 Apr
Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene.
2010 Feb 2
Endometrial safety: a key hurdle for selective estrogen receptor modulators in development.
2010 May-Jun
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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