Tamoxifen, =99%

Synonym: (Z)-1-(p-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene, trans-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine

CAS Number: 10540-29-1

Linear Formula: C₆H₅C(C₂H₅)=C(C₆H₅)C₆H₄OCH₂CH₂N(CH₃)₂

Molecular Weight: 371.51

EC Number: 234-118-0

MDL number: MFCD00010454

PubChem Substance ID: 24900307

General Description
Tamoxifen is a selective estrogen response modifier (SERM), protein kinase C inhibitor and anti-angiogenetic factor. Tamoxifen is a prodrug that is metabolized to active metabolites 4-hydroxytamoxifen (4-OHT) and endoxifen by cytochrome P450 isoforms CYP2D6 and CYP3A4. In breast cancer, the gene repressor activity of tamoxifen against ERBB2 is dependent upon PAX2. Blocks estradiol-stimulated VEGF production in breast tumor cells.

Preparation Note
Tamoxifen is soluble in chloroform at 50 mg/ml and yields a clear, colorless to faint yellow solution. It is also soluble in methanol, ethanol, 2-propanol and propylene glycol. Stock solutions of tamoxifen can also be prepared in DMSO at 10 mM. However, it is practically insoluble in water (solubility is <0.01%, 20° C). Solutions are sensitive to UV light, and DMSO solutions are stable when stored at -20° C in the dark.

Application
Tamoxifen has been used to facilitate the recombination of ect2^flox allele in mouse organs⁹¹. It has also been used to study its effect on lipopolysaccharide (LPS)-induced microglial activation⁹².

Biochem/physiol Actions
Protein kinase C inhibitor. Induces apoptosis in human malignant glioma cell lines. Tamoxifen and its metabolite 4-hydroxytamoxifen are selective estrogen response modifiers (SERMs) that act as estrogen antagonists in mammary gland. Blocks estradiol-stimulated VEGF production in breast tumor cells.