Arzoxifene information

Arzoxifene
Clinical data
Other names	LY-353381
Routes of; administration	By mouth
Drug class	Selective estrogen receptor modulator
Identifiers
	IUPAC name 2-(4-Methoxyphenyl)-3-[4-(2-piperidin-1-ylethoxy)phenoxy]-1-benzothiophen-6-ol;
CAS Number	182133-25-1 ; 182133-27-3 (hydrochloride);
PubChem CID	179337;
ChemSpider	156104 ;
UNII	E569WG6E60;
KEGG	D02993;
ChEMBL	ChEMBL226267 ;
CompTox Dashboard (EPA)	DTXSID10171255 ;
Chemical and physical data
Formula	C28H29NO4S
Molar mass	475.60 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC=C(C=C1)C2=C(C3=C(S2)C=C(C=C3)O)OC4=CC=C(C=C4)OCCN5CCCCC5;
	InChI 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 ; Key:MCGDSOGUHLTADD-UHFFFAOYSA-N ;
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Arzoxifene (INNTooltip International Nonproprietary Name; developmental code name LY-353381) is a selective estrogen receptor modulator (SERM) of the benzothiophene group which was never marketed.^[1] It is a potent estrogen antagonist in mammary and uterine tissue while acting as an estrogen agonist to maintain bone density and lower serum cholesterol. Arzoxifene is a highly effective agent for prevention of mammary cancer induced in the rat by the carcinogen nitrosomethylurea and is significantly more potent than raloxifene in this regard. Arzoxifene is devoid of the uterotrophic effects of tamoxifen, suggesting that, in contrast to tamoxifen, it is unlikely that the clinical use of arzoxifene will increase the risk of developing endometrial carcinoma.

^ Overk CR, Peng KW, Asghodom RT, et al. (2007). "Structure-activity relationships for a family of benzothiophene selective estrogen receptor modulators including raloxifene and arzoxifene". ChemMedChem. 2 (10): 1520–6. doi:10.1002/cmdc.200700104. PMID 17654759. S2CID 35664796.

[pmid17654759-1] Overk CR, Peng KW, Asghodom RT, et al. (2007). "Structure-activity relationships for a family of benzothiophene selective estrogen receptor modulators including raloxifene and arzoxifene". ChemMedChem. 2 (10): 1520–6. doi:10.1002/cmdc.200700104. PMID 17654759. S2CID 35664796.

Arzoxifene information

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Clinical data

Other names	LY-353381
Routes of administration	By mouth
Drug class	Selective estrogen receptor modulator
Identifiers
IUPAC name 2-(4-Methoxyphenyl)-3-[4-(2-piperidin-1-ylethoxy)phenoxy]-1-benzothiophen-6-ol
CAS Number	182133-25-1^Y 182133-27-3 (hydrochloride)
PubChem CID	179337
ChemSpider	156104^Y
UNII	E569WG6E60
KEGG	D02993
ChEMBL	ChEMBL226267^Y
CompTox Dashboard (EPA)	DTXSID10171255
Chemical and physical data
Formula	C₂₈H₂₉NO₄S
Molar mass	475.60 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=CC=C(C=C1)C2=C(C3=C(S2)C=C(C=C3)O)OC4=CC=C(C=C4)OCCN5CCCCC5
InChI 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^Y Key:MCGDSOGUHLTADD-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)