Structure via PubChem · Public domain (PubChem)
arzoxifene
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Arzoxifene (; developmental code name LY-353381) is a selective estrogen receptor modulator (SERM) of the benzothiophene group which was never marketed. 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 tamox
Chemical data
- Formula
- C28H29NO4S
- Molecular weight
- 475.6 g/mol
- IUPAC name
- 2-(4-methoxyphenyl)-3-[4-(2-piperidin-1-ylethoxy)phenoxy]-1-benzothiophen-6-ol
- SMILES
- COC1=CC=C(C=C1)C2=C(C3=C(S2)C=C(C=C3)O)OC4=CC=C(C=C4)OCCN5CCCCC5
- InChIKey
- MCGDSOGUHLTADD-UHFFFAOYSA-N
- XLogP
- 6.6
- Polar surface area
- 79.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- postmenopausal osteoporosis, osteoporosis, breast neoplasm, breast cancer
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 475.182
Show 3 more facts
- canonical SMILES
- COC1=CC=C(C=C1)C2=C(C3=C(S2)C=C(C=C3)O)OC4=CC=C(C=C4)OCCN5CCCCC5
- chemical formula
- C₂₈H₂₉NO₄S
- Commons category
- Arzoxifene
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Pharmacology
- Research
- References
- External links
Arzoxifene (; developmental code name LY-353381) is a selective estrogen receptor modulator (SERM) of the benzothiophene group which was never marketed. 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.
==Pharmacology== Arzoxifene is a selective estrogen receptor modulator (SERM), and hence is a mixed agonist and antagonist of the estrogen receptor with tissue-selective estrogenic and antiestrogenic activity. It has antiestrogenic effects in the breast, mixed estrogenic and antiestrogenic effects in the uterus, and estrogenic effects in bone. The medication has been found to suppress gonadotropin levels in postmenopausal women, increase sex hormone-binding globulin levels, and decrease insulin-like growth factor 1 and insulin-like growth factor-binding protein 3 levels.
Excerpted from Wikipedia’s “arzoxifene” article, available under the CC BY-SA 4.0 licence.