SML1666
4-Hydroxytamoxifen
≥98% (HPLC), solution, Estrogen receptor antagonist
Synonym(s):
4-OHT, cis/trans-4-Hydroxytamoxifen
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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
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.
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.
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.
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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
Regulatory Information
危险化学品
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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)
Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants.
Sun D, et al.
Breast Cancer Research, 8(4), R50-R50 (2006)
Izumi Kaji et al.
JCI insight, 6(16) (2021-07-02)
Functional loss of myosin Vb (MYO5B) induces a variety of deficits in intestinal epithelial cell function and causes a congenital diarrheal disorder, microvillus inclusion disease (MVID). The impact of MYO5B loss on differentiated cell lineage choice has not been investigated.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML1666-1ML | 04061838093042 |