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Merck

T9262

Sigma-Aldrich

Tamoxifen citrate salt

≥99% (TLC), powder, PKC inhibitor

Synonym(s):

(Z)-1-(p-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene

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About This Item

Empirical Formula (Hill Notation):
C26H29NO · C6H8O7
CAS Number:
54965-24-1
Molecular Weight:
563.64
EC Number:
259-415-2
MDL number:
MFCD00058321
UNSPSC Code:
12161501
PubChem Substance ID:
24278059
NACRES:
NA.77

Key Documents

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Product Name

Tamoxifen citrate salt, ≥99%

Quality Level

200

Assay

≥99%

solubility

methanol: soluble 50 mg/mL, clear, colorless

originator

AstraZeneca

storage temp.

2-8°C

SMILES string

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

InChI

1S/C26H29NO.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-18H,4,19-20H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25-;

InChI key

FQZYTYWMLGAPFJ-OQKDUQJOSA-N

Gene Information

human ... ESR1(2099), PRKCA(5578), PRKCB(5579), PRKCD(5580), PRKCE(5581), PRKCG(5582), PRKCH(5583), PRKCI(5584)

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Application

Tamoxifen has been used for analyzing its effects on radiation sensitivity and steroid receptor content in human breast cancer cells. It has also been used for studying the accumulation of triacylglycerol in hepatic tissues of female rats. Furthermore, studies have reported that environmental magnetic fields can block antiproliferative functions of tamoxifen in human breast cancer cells.

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.

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 is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
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 citrate salt dissolves in methanol at 50 mg/ml to yield a clear, colorless solution.

Signal Word

Danger

Hazard Statements

H302,H350,H360D,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - 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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Certificates of Analysis (COA)

Lot/Batch Number
WXBD3760V
WXBC9434V
WXBC6121V
WXBC1372
WXBB6777V

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J D Harland et al.
Bioelectromagnetics, 18(8), 555-562 (1997-01-01)
We have previously reported that environmental-level magnetic fields (1.2 microT [12 milligauss], 60 Hz) block the growth inhibition of the hormone melatonin (10(-9) M) on MCF-7 human breast cancer cells in vitro. We now report that the same 1.2 microT
Oddrun Anita Gudbrandsen et al.
Journal of lipid research, 47(10), 2223-2232 (2006-07-26)
Tamoxifen can induce hepatic steatosis in women. In this study, we wanted to elucidate the mechanism behind the tamoxifen-induced accumulation of triacylglycerol in liver in female rats, and we hoped to prevent this development by combination treatment with the modified
G H Paulsen et al.
Acta oncologica (Stockholm, Sweden), 35(8), 1011-1019 (1996-01-01)
Possible influences of tamoxifen and estradiol on in vitro radiation sensitivity and cellular receptor content after irradiation and/or tamoxifen treatment were studied in breast cancer cell lines; estrogen receptor (ER) and progesterone receptor (PgR) positive cell lines MCF-7 and MCF-7/TAM(R)-1
K I Pritchard
Journal of internal medicine, 274(2), 144-152 (2013-07-13)
Hormonal therapy for breast cancer is the first targeted therapy used in any type of cancer. It was used successfully without a known target for more than 50 years before Jensen described the oestrogen receptor (ER) in the 1960s. Subsequently, it
Kevin S Hughes et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 31(19), 2382-2387 (2013-05-22)
To determine whether there is a benefit to adjuvant radiation therapy after breast-conserving surgery and tamoxifen in women age ≥ 70 years with early-stage breast cancer. Between July 1994 and February 1999, 636 women (age ≥ 70 years) who had
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