Toremifene

Product Details – Toremifene

Toremifene is a nonsteroidal selective estrogen receptor modulator (SERM) belonging to the triphenylethylene class of compounds. It is structurally related to other SERMs and is commonly utilized in investigational research for the study of estrogen receptor signaling and ligand-receptor interactions.

Toremifene is frequently examined in its citrate salt form due to improved solubility characteristics. The compound serves as a reference ligand in in vitro studies exploring receptor binding dynamics, transcriptional modulation, and endocrine pathway regulation.

Mechanism of Action

Toremifene functions as a competitive ligand for estrogen receptors (ERα and ERβ), binding to the receptor’s ligand-binding domain and inducing conformational changes that influence transcriptional activity.

In research models, receptor binding by toremifene alters the recruitment of coactivators and corepressors, leading to modulation of estrogen-responsive gene expression. This results in tissue-selective receptor activity, dependent on cellular context and cofactor availability in experimental systems.

Similar to other SERMs, toremifene exhibits mixed agonist-antagonist properties in preclinical models, making it a valuable compound for studying selective estrogen receptor modulation at the molecular level.

Properties

• Molecular Formula: C26H28ClNO
• Molecular Weight: 405.91 g/mol 
• CAS Number: 89778-27-8
• PubChem CID: 3005573
• Synonyms: Toremifene, Toremifene citrate, Fareston, FC 1157a, (Z)-Toremifene

Research Applications

Applications in in vitro and experimental models include:

• Investigation of estrogen receptor (ER) binding affinity and ligand selectivity
• Study of transcriptional regulation via estrogen response elements (EREs)
• Analysis of coactivator and corepressor recruitment in nuclear receptor signaling
• Comparative evaluation of SERM compounds in preclinical models
• Exploration of structure-activity relationships (SAR) within the triphenylethylene class

Its well-characterized receptor interaction profile makes toremifene a valuable tool for mechanistic studies of selective estrogen receptor modulation in controlled research environments.

References:

• Zhao, Y., Ren, J., Harlos, K., Jones, D. M., Zeltina, A., Bowden, T. A., Padilla-Parra, S., Fry, E. E., & Stuart, D. I. (2016). Toremifene interacts with and destabilizes the Ebola virus glycoprotein. Nature, 535(7610), 169–172. https://doi.org/10.1038/nature18615
• Raghow, S., Hooshdaran, M. Z., Katiyar, S., & Steiner, M. S. (2002). Toremifene prevents prostate cancer in the transgenic adenocarcinoma of mouse prostate model. PubMed, 62(5), 1370–1376. https://pubmed.ncbi.nlm.nih.gov/11888907
• Anttila, M., Valavaara, R., Kivinen, S., & Maenpaa, J. (1990). Pharmacokinetics of toremifene. Journal of Steroid Biochemistry, 36(3), 249–252. https://doi.org/10.1016/0022-4731(90)90019-o