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Merck

85256

Tamoxifen

analytical standard

Synonym(s):

(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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All Photos(2)

About This Item

Linear Formula:
C6H5C(C2H5)=C(C6H5)C6H4OCH2CH2N(CH3)2
CAS Number:
10540-29-1
Molecular Weight:
371.51
NACRES:
NA.24
PubChem Substance ID:
329769367
UNSPSC Code:
41116107
EC Number:
234-118-0
MDL number:
MFCD00010454

Product Name

Tamoxifen, analytical standard

InChI key

NKANXQFJJICGDU-QPLCGJKRSA-N

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-

SMILES string

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

grade

analytical standard

assay

≥98.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

impurities

≤0.5% water

mp

97-98 °C (lit.)

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... ESR1(2099)

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Estrogen antagonist in mammary gland. Blocks estradiol-stimulated VEGF production in breast tumor cells. Protein kinase C inhibitor.
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.

pictograms

Health hazardEnvironment
GHS08,GHS09

signalword

Danger

Hazard Classifications

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

Storage Class

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN0185
BCCL6241
BCCK6230
BCCH5113
BCCG8921

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P Saladores et al.
The pharmacogenomics journal, 15(1), 84-94 (2014-08-06)
Tamoxifen is the standard-of-care treatment for estrogen receptor-positive premenopausal breast cancer. We examined tamoxifen metabolism via blood metabolite concentrations and germline variations of CYP3A5, CYP2C9, CYP2C19 and CYP2D6 in 587 premenopausal patients (Asians, Middle Eastern Arabs, Caucasian-UK; median age 39
Marcelo A Mori et al.
The Journal of clinical investigation, 124(8), 3339-3351 (2014-07-02)
miRNAs are important regulators of biological processes in many tissues, including the differentiation and function of brown and white adipocytes. The endoribonuclease dicer is a major component of the miRNA-processing pathway, and in adipose tissue, levels of dicer have been
Wataru Ise et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(32), 11792-11797 (2014-07-30)
In primary humoral responses, B-cell lymphoma 6 (Bcl6) is a master regulator of follicular helper T (TFH) cell differentiation; however, its activation mechanisms and role in memory responses remain unclear. Here we demonstrate that survival of CXCR5(+) TFH memory cells
Takeo Nakaya et al.
Cancer research, 74(10), 2882-2891 (2014-03-15)
The intestinal epithelium maintains homeostasis by a self-renewal process involving resident stem cells, including Lgr5(+) crypt-base columnar cells, but core mechanisms and their contributions to intestinal cancer are not fully defined. In this study, we examined a hypothesized role for
L Binkhorst et al.
Clinical pharmacology and therapeutics, 92(4), 431-433 (2012-08-23)
Traditionally, all patients treated with tamoxifen receive a standard dose. A number of studies claimed a clinically relevant impact of cytochrome P450 2D6 (CYP2D6) genotype on outcome, and therefore genotyping before tamoxifen therapy was advocated. Recent data showed that adequate
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