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T5648

Sigma-Aldrich

Tamoxifen

≥99%

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Synonym(s):
(Z)-1-(p-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene, trans-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine
Linear Formula:
C6H5C(C2H5)=C(C6H5)C6H4OCH2CH2N(CH3)2
CAS Number:
Molecular Weight:
371.51
EC Number:
MDL number:
PubChem Substance ID:

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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1 of 4

This Item
85256T2859T9262
Tamoxifen &#8805;99%

Sigma-Aldrich

T5648

Tamoxifen

Tamoxifen analytical standard

Supelco

85256

Tamoxifen

Tamoxifen powder, Suitable for cell culture

Sigma-Aldrich

T2859

Tamoxifen

Tamoxifen citrate salt &#8805;99%

Sigma-Aldrich

T9262

Tamoxifen citrate salt

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

solubility

-

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

solubility

methanol: soluble 50 mg/mL, clear, colorless

originator

AstraZeneca

originator

-

originator

-

originator

AstraZeneca

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

mp

97-98 °C (lit.)

mp

97-98 °C (lit.)

mp

97-98 °C (lit.)

mp

-

(Z)-1-(p-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene, trans-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine, Tamoxifen citrate, Lopac-T-9262, ICI-46,474, ICI-46474, ICI-47699, Nolvadex, Novaldex, Soltamox, Tamoxifen Citrate, Tomaxithen, PKC, SERM, apoptosis, P450, CYP2D6, CYP3A4, PAX2, ERBB2, angiogenesis, .

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(Z)-1-(p-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene, trans-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine, Tamoxifen citrate, Lopac-T-9262, ICI-46,474, ICI-46474, ICI-47699, Nolvadex, Novaldex, Soltamox, Tamoxifen Citrate, Tomaxithen, PKC, SERM, apoptosis, P450, CYP2D6, CYP3A4, PAX2, ERBB2, angiogenesis,.

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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.

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tamoxifen citrate European Pharmacopoeia (EP) Reference Standard

T0014000

Tamoxifen citrate

USP

USP

1148806

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4-Hydroxytamoxifen (E) and (Z) isomers (50:50), analytical standard

Supelco

94873

4-Hydroxytamoxifen

Tamoxifen Citrate Tamoxifen is a potent synthetic anti-estrogenic agent.

Sigma-Aldrich

579000

Tamoxifen Citrate

Peanut oil delivery vehicle for lipophilic compounds

Sigma-Aldrich

P2144

Peanut oil

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
Meimei Liu et al.
Aquatic toxicology (Amsterdam, Netherlands), 213, 105220-105220 (2019-06-16)
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
Microglia-Specific Expression of Olfml3 Is Directly Regulated by Transforming Growth Factor ?1-Induced Smad2 Signaling
Neidert N, et al.
Frontiers in Immunology, 9, 1728-1728 (2018)
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Cancer research, 79(16), 4086-4098 (2019-06-27)
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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Cancer research, 74(10), 2882-2891 (2014-03-15)
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Chromatograms

application for HPLC, application for SPE

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