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T5648

Sigma-Aldrich

Tamoxifen

≥99% (TLC), powder, PKC inhibitor

Synonym(s):

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

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About This Item

Linear Formula:
C6H5C(C2H5)=C(C6H5)C6H4OCH2CH2N(CH3)2
CAS Number:
Molecular Weight:
371.51
EC Number:
MDL number:
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.54

product name

Tamoxifen, ≥99%

sterility

(Not packaged in a sterile environment)

assay

≥99%

mp

97-98 °C (lit.)

solubility

H2O: insoluble <0.1% at 20 °C
chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow
2-propanol: soluble
DMSO: soluble
ethanol: soluble
methanol: soluble
propylene glycol: soluble

antibiotic activity spectrum

neoplastics

mode of action

enzyme | inhibits

originator

AstraZeneca

storage temp.

2-8°C

SMILES string

CC\C(c1ccccc1)=C(/c2ccccc2)c3ccc(OCCN(C)C)cc3

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

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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.

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 ect2flox allele in mouse organs
  • to study its effect on lipopolysaccharide (LPS)-induced microglial activation

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.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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.

pictograms

Health hazardEnvironment

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Repr. 1B

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


Certificates of Analysis (COA)

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Tamoxifen (TAM) is an antiestrogenic agent and can enter the aquatic environment in wastewater. It has been reported that TAM can induce hepatic steatosis in vertebrates, however, the effects of TAM exposure on lipid metabolism of hepatopancreas in crustaceans remains
Bon-Kyoung Koo et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(24), 7548-7550 (2015-05-30)
Rnf43 (RING finger protein 43) and Znrf3 (zinc/RING finger protein 3) (RZ) are two closely related transmembrane E3 ligases, encoded by Wnt target genes, that remove surface Wnt (wingless-int) receptors. The two genes are mutated in various human cancers. Such
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Tamoxifen
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Tripartite motif (TRIM) family proteins participate in a variety of important cellular processes, including apoptosis, cell-cycle arrest, DNA repair, and senescence. In this study, we demonstrated that a novel TRIM family member, TRIM67, was commonly silenced in colorectal cancer and

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Chromatograms

application for HPLC, application for SPE

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