ospemifene   Click here for help

GtoPdb Ligand ID: 7349

Synonyms: FC-1271 | Osphena® | Senshio®
Approved drug
ospemifene is an approved drug (FDA (2013), EMA (2015))
Compound class: Synthetic organic
Comment: Ospemifene is a selective estrogen receptor modulator (SERM) [2]. Like other SERMs it has mixed agonist/antagonist activities that are tissue-dependent.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 29.46
Molecular weight 378.14
XLogP 6.29
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES ClCCC(=C(c1ccccc1)c1ccc(cc1)OCCO)c1ccccc1
Isomeric SMILES ClCC/C(=C(\c1ccccc1)/c1ccc(cc1)OCCO)/c1ccccc1
InChI InChI=1S/C24H23ClO2/c25-16-15-23(19-7-3-1-4-8-19)24(20-9-5-2-6-10-20)21-11-13-22(14-12-21)27-18-17-26/h1-14,26H,15-18H2/b24-23-
Bioactivity Comments
In vitro, ospemifene binds human ERα and ERβ with similar affinity, but with lower affinity than estradiol [3]. Ospemifene exhibits antagonist (anti-estrogenic) activity in breast cancer cells, and agonist (estrogenic) activity in vaginal epithelium and stroma.
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Estrogen receptor-α Primary target of this compound Hs Antagonist Antagonist 6.4 pKi - 3
pKi 6.4 (Ki 3.8x10-7 M) [3]
Estrogen receptor-β Primary target of this compound Hs Antagonist Antagonist 6.4 pKi - 3
pKi 6.4 (Ki 4.1x10-7 M) [3]