Tamoxifen

SIGMA/T5648 - ≥99%

Synonym: trans-Tamoxifen; (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
Empirical Formula (Hill Notation): C₂₆H₂₉NO
Molecular Weight: 371.51
EC Number: 234-118-0
MDL Number: MFCD00010454
Linear Formula: C₆H₅C(C₂H₅)=C(C₆H₅)C₆H₄OCH₂CH₂N(CH₃)₂
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-T5648-1G	1 g	$297.00 1/EA	Add To Favorites
45-T5648-5G	5 g	$1190.00 1/EA	Add To Favorites

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Properties
Descriptions
Safety Info.
Basic Data

antibiotic activity spectrum	neoplastics
assay	≥99%
InChI	1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
InChI key	NKANXQFJJICGDU-QPLCGJKRSA-N
mode of action	enzyme \| inhibits
mp	97-98 °C (lit.)
originator	AstraZeneca
SMILES string	CCC(c1ccccc1)=C(/c2ccccc2)c3ccc(OCCN(C)C)cc3
solubility	2-propanol: soluble
	chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow
	DMSO: soluble
	ethanol: soluble
	H₂O: insoluble <0.1% at 20 °C
	methanol: soluble
	propylene glycol: soluble
sterility	(Not packaged in a sterile environment)
storage temp.	2-8°C

Application:	Tamoxifen has been used: in the MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) assay and crystal violet staining assay to access cell viability to induce Dicer ablation in Dicer-conditional mice, to study the effects of Dicer deficiency on adipocyte differentiation and function. to study its biological effects on the glucocorticoid (GC)-resistant cell line Jurkat, derived from acute lymphoblastic leukemia of T lineage (T-ALL) to study the physiological effects of tamoxifen treatment on the hypothalamus-POA mediated by estrogen receptor alpha (ERα) in mice to induce Cre recombinase activity for gene manipulation. to facilitate the recombination of the ect2^flox allele in mouse organs to study its effect on lipopolysaccharide (LPS)-induced microglial activation
Biochem/physiol Actions:	Estrogen antagonist in mammary gland. Blocks estradiol-stimulated VEGF production in breast tumor cells. Protein kinase C inhibitor.
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.
Features and Benefits:	This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm .
Features and Benefits:	This compound was developed by AstraZeneca . To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here .
General description:	Tamoxifen (TC), a selective estrogen receptor modulator (SERM), is used against breast cancer in both men and women. It also acts as a prophylactic agent against breast cancer in women. This protein kinase C inhibitor and anti-angiogenetic factor 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. TC blocks estradiol-stimulated vascular endothelial growth factor (VEGF) production in breast tumor cells. Patients with estrogen receptor-positive tumors are more likely to benefit from tamoxifen. It exhibits both estrogenic agonist and antagonist effects by selectively binding to estrogen receptors in different parts of the body. This nonsteroidal triphenylethylene derivative suppresses tumor growth and has been reported to be a carcinogen and teratogen in animals. Additionally, TC may also protect bone from estrogen-deficiency bone loss, lower plasma cholesterol, and have been implicated in liver carcinogenesis in rats. Other actions of TC include the reduction of plasma levels of insulin-like growth factor, induction of cells surrounding cancer cells to secrete transforming growth factor β, and inhibition of membrane lipid peroxidation, likely by decreasing membrane fluidity.
Other Notes:	2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research
Other Notes:	This product is not packaged in a sterile environment.
Packaging:	1, 5 g in glass bottle
Preparation Note:	Tamoxifen is relatively stable. The powder should be stable for at least two years when stored desiccated at 2-8C, protected from light.
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.

Symbol	GHS08,GHS09
Signal word	Danger
Hazard statements	H350 - H360 - H410
Precautionary statements	P201 - P273 - P308 + P313
Hazard Codes	T
Risk Statements	45-60-61-64
Safety Statements	53-45
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥99%
mp	97-98 °C (lit.)
Storage Temp.	2-8°C
UNSPSC	12161501

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