SML1666
4-Hydroxytamoxifen
≥98% (HPLC), solution, Estrogen receptor antagonist
Synonym(s):
4-OHT, cis/trans-4-Hydroxytamoxifen
Sign In to View Organizational & Contract Pricing.
Select a Size
Change View
About This Item
Empirical Formula (Hill Notation):
C26H29NO2
CAS Number:
Molecular Weight:
387.51
UNSPSC Code:
12352200
NACRES:
NA.77
Form:
solution
Quality level:
Product Name
4-Hydroxytamoxifen Ready Made Solution, 5 mg/mL in ethanol: isopropanol (95:5)
biological source
synthetic
Quality Level
form
solution
concentration
5 mg/mL in ethanol: isopropanol (95:5)
shipped in
dry ice
storage temp.
−20°C
SMILES string
N(CCOc1ccc(cc1)\C(=C(\CC)/c3ccccc3)\c2ccc(cc2)O)(C)C
InChI
1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
InChI key
TXUZVZSFRXZGTL-QPLCGJKRSA-N
Biochem/physiol Actions
4-Hydroxytamoxifen is an active metabolite of Tamoxifen.
4-Hydroxytamoxifen is an active metabolite of Tamoxifen. 4-Hydroxytamoxifen is formed by cytochrome P450 2D6 in human liver and is a potent and selective estrogen receptor antagonist. 4-Hydroxytamoxifen has been used to stimulate LC3 lipidation and to form autophagic vesicles in a superoxide-dependent manner. Tamoxifen and 4-Hydroxytamoxifen markedly induce cytochrome P450 3A4 (a major drug-metabolizing enzyme) in primary cultures of human hepatocytes. 4-Hydroxytamoxifen undergoes a cis-trans (E-Z) isomerization, a process that occurs in all common laboratory solvents.
Trans isoform of 4-hydroxytamoxifen possesses antiestrogenic activity, while the cis 4-hydroxytamoxifen serves as a key agonist for estrogen receptor. 4-Hydroxytamoxifen promotes apoptosis via activation of p38 pathway in breast cancer cell cultures.
Preparation Note
4-Hydroxytamoxifen is provided in a 13 mM solution. The recommended working concentration is 10-100 μM. Therefore, 4-Hydroxytamoxifen Ready Made Solution should be diluted 1:130 - 1:1,300 in cell culture media.
Disclaimer
Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.
Still not finding the right product?
Explore all of our products under 4-Hydroxytamoxifen Ready Made Solution
signalword
Danger
Hazard Classifications
Aquatic Chronic 3 - Carc. 1B - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 1B
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
55.4 °F
flash_point_c
13 °C
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants.
Sun D, et al.
Breast Cancer Research, 8(4), R50-R50 (2006)
Activation of the p38 mitogen-activated protein kinase pathway by estrogen or by 4-hydroxytamoxifen is coupled to estrogen receptor-induced apoptosis.
Zhang C C and Shapiro D J
The Journal of Biological Chemistry, 275(1), 479-486 (2000)
Jinming Zhao et al.
iScience, 24(12), 103425-103425 (2021-12-09)
We previously showed stabilization of NIK-induced activation of NF-κB non-canonical signaling suppresses MLL-AF9-induced AML. In the current study, we demonstrate that deletion of NF-κB non-canonical RelB prevents the inhibitory effect of NIK stabilization in MLL-AF9 AML. Mechanistically, RelB suppresses its