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T9262

Sigma-Aldrich

Tamoxifen citrate salt

≥99%

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Synonym(s):
(Z)-1-(p-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene
Empirical Formula (Hill Notation):
C26H29NO · C6H8O7
CAS Number:
Molecular Weight:
563.64
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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1 of 4

This Item
H7904T00140001643306
vibrant-m

T9262

Tamoxifen citrate salt

vibrant-m

H7904

(Z)-4-Hydroxytamoxifen

vibrant-m

T0014000

Tamoxifen citrate

vibrant-m

1643306

Tamoxifen citrate

Quality Level

200

Quality Level

300

Quality Level

-

Quality Level

-

originator

AstraZeneca

originator

AstraZeneca

originator

-

originator

-

solubility

methanol: soluble 50 mg/mL, clear, colorless

solubility

methanol: 10 mg/mL, ethanol: 20 mg/mL (with heating)

solubility

-

solubility

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Gene Information

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

Gene Information

human ... ESR1(2099), ESR2(2100), ESRRG(2104), IL6(3569)
rat ... Ar(24208), Esr1(24890), Esr2(25149)

Gene Information

human ... ESR1(2099)

Gene Information

human ... ESR1(2099)

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

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.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Repr. 1B

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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4-Hydroxytamoxifen ≥70% Z isomer (remainder primarily E-isomer)

Sigma-Aldrich

H6278

4-Hydroxytamoxifen

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

Supelco

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4-Hydroxytamoxifen

H-7 dihydrochloride ≥98% (HPLC)

Sigma-Aldrich

I7016

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USP

USP

1148806

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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
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
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
P Fox et al.
British journal of cancer, 109(1), 147-153 (2013-06-20)
The host inflammatory response has a vital role in carcinogenesis and tumour progression. We examined the prognostic value of inflammatory markers (albumin, white-cell count and its components, and platelets) in pre-treated patients with advanced renal cell carcinoma (RCC). Using data

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