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SML1666

Sigma-Aldrich

4-Hydroxytamoxifen

≥98% (HPLC), solution, Tamoxifen metabolite

Synonyme(s) :

4-OHT, cis/trans-4-Hydroxytamoxifen

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About This Item

Formule empirique (notation de Hill):
C26H29NO2
Numéro CAS:
68392-35-8
Poids moléculaire :
387.51
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

product name

4-Hydroxytamoxifen Ready Made Solution, 5 mg/mL in ethanol: isopropanol (95:5)

Source biologique

synthetic

Niveau de qualité

200

Forme

solution

Concentration

5 mg/mL in ethanol: isopropanol (95:5)

Conditions d'expédition

dry ice

Température de stockage

−20°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-

Clé InChI

TXUZVZSFRXZGTL-QPLCGJKRSA-N

Actions biochimiques/physiologiques

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.

Notes préparatoires

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.

Pictogrammes

FlameHealth hazardExclamation mark
GHS02,GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H225,H319,H350,H360FD,H412

Classification des risques

Aquatic Chronic 3 - Carc. 1B - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 1B

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

55.4 °F

Point d'éclair (°C)

13 °C

Certificats d'analyse (COA)

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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.
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