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General Properties, Chemistry, Biological Action, Structure Activity Relationship and Therapeutic Applications of Tamoxifen

Tamoxifen is a selective estrogen receptor modulator (SERM) that is used primarily to treat and prevent breast cancer. Here's an overvie...



Tamoxifen is a selective estrogen receptor modulator (SERM) that is used primarily to treat and prevent breast cancer. Here's an overview of its general properties, chemistry, biological action, structure-activity relationship, and therapeutic applications:

General Properties:

Chemical name: (Z)-2-[4-(1,2-diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine

Molecular formula: C26H29NO

Molecular weight: 371.52 g/mol

Melting point: 97-98°C

Solubility: slightly soluble in water, soluble in ethanol and methanol

Route of administration: oral

Chemistry:

Tamoxifen is a nonsteroidal compound with an active metabolite, endoxifen. It belongs to the triphenylethylene group of compounds, which act as estrogen receptor antagonists in breast tissue and as partial agonists in other tissues. Tamoxifen is a racemic mixture of two enantiomers, with the (Z)-isomer being the biologically active form.


Biological Action:

Tamoxifen binds to the estrogen receptor (ER) and blocks the binding of estrogen, thereby preventing estrogen-induced proliferation of breast cancer cells. It is also believed to induce apoptosis (programmed cell death) in breast cancer cells. In addition, tamoxifen has estrogen-like effects on bone and lipid metabolism, which may contribute to its therapeutic benefits.

Structure-Activity Relationship:

The structure-activity relationship of tamoxifen is complex, as it acts as an antagonist in breast tissue and a partial agonist in other tissues. The (Z)-isomer is the biologically active form, with the (E)-isomer having little to no activity. Modifications to the tamoxifen molecule can alter its estrogenic and antiestrogenic activity, as well as its affinity for the ER.

for more detailed SAR please read this post

SAR of Tamoxifen

Therapeutic Applications:

Tamoxifen is primarily used to treat and prevent breast cancer. It is indicated for the treatment of estrogen receptor-positive breast cancer in both pre- and postmenopausal women. It may also be used to reduce the risk of breast cancer in women at high risk, as well as to treat gynecomastia (enlargement of breast tissue in men). Tamoxifen has also been investigated for its potential therapeutic applications in other types of cancer, such as endometrial and ovarian cancer.

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