Arzoxifene

Title: Arzoxifene
CAS Registry Number: 182133-25-1
CAS Name: 2-(4-Methoxyphenyl)-3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]benzo[b]thiophene-6-ol
Additional Names: [6-hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]2-(4-methoxyphenyl)]benzo[b]thiophene
Manufacturers' Codes: LY-353381
Molecular Formula: C28H29NO4S
Molecular Weight: 475.60
Percent Composition: C 70.71%, H 6.15%, N 2.95%, O 13.46%, S 6.74%
Literature References: Selective estrogen receptor modulator (SERM). Prepn: A. D. Palkowitz, K. J. Thrasher, EP 729956; idem, US 5981765 (1996, 1999 both to Eli Lilly). Pharmacology: M. Sato et al., Endocrinology 139, 4642 (1998); N. Suh et al., Cancer Res. 61, 8412 (2001). Clinical pharmacokinetics: P. N. Münster et al., J. Clin. Oncol. 19, 2002 (2001). Review of clinical evaluations and therapeutic potential: S. Chan, Semin. Oncol. 29, Suppl. 1, 129-133 (2002).
Properties: Solid from hexane, mp 174-176°.
Melting point: mp 174-176°
Derivative Type: Hydrochloride
CAS Registry Number: 182133-27-3
Molecular Formula: C28H29NO4S.HCl
Molecular Weight: 512.06
Percent Composition: C 65.68%, H 5.91%, N 2.74%, O 12.50%, S 6.26%, Cl 6.92%
Properties: Crystals from ethanol/ethyl acetate, mp 156-160°.
Melting point: mp 156-160°
Therap-Cat: Antineoplastic (hormonal).
Keywords: Antineoplastic (Hormonal); Antiestrogens; Selective Estrogen Receptor Modulator (SERM).
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Arzoxifene
Arzoxifene.svg
Identifiers
CAS number 182133-25-1 N
PubChem 179337
ChemSpider 156104 YesY
ChEMBL CHEMBL226267 YesY
Jmol-3D images Image 1
Properties
Molecular formula C28H29NO4S
Molar mass 475.60 g/mol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Arzoxifene is a selective estrogen receptor modulator.[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.