H7904
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H7904
Sigma
4-Hydroxytamoxifen
≥98% (HPLC), powder
| Synonym: | 4-OHT, trans-4-Hydroxytamoxifen, (Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol |
| CAS Number: | 68047-06-3 |
| Linear Formula: | C26H29NO2 |
| Molecular Weight: | 387.51 |
| MDL number: | MFCD00278780 |
| PubChem Substance ID: | 24895814 |
Description
| Biochem/physiol Actions | Metabolite of the chemotherapeutic drug tamoxifen, exhibiting more potent estrogen agonist/antagonist activity than the parent drug. Also active as intra-membranous inhibitor of lipid peroxidation. |
| General description | 4-Hydroxytamoxifen is the active metabolite of tamoxifen which binds estrogen receptors (ER) and estrogen-related receptors (ERR) with estrogenic and anti-estrogenic effects. It is a selective estrogen receptor modulator (SERM). |
Properties
| assay | ≥98% (HPLC) |
| form | powder |
| color | white |
| solubility | 95% ethanol: 20 mg/mL |
| Gene Information | human ... ESR1(2099), ESR2(2100), ESRRG(2104), IL6(3569) |
| rat ... Ar(24208), Esr1(24890), Esr2(25149) | |
| storage temp. | 2-8°C |
Safety
| Personal Protective Equipment | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard Codes | Xn |
| Risk Statements | 20/21/22-63 |
| Safety Statements | 22-23-36 |
| WGK Germany | 3 |
| RTECS | SL1210000 |
References
| reference | Murphy CS, et al., Structure-function relationships of hydroxylated metabolites of tamoxifen that control the proliferation of estrogen-responsive T47D breast cancer cells in vitro Mol. Pharmacol. 38, 737-743, (1990) Abstract |
| Zhang CC, and Shapiro DJ., Activation of the p38 mitogen-activated protein kinase pathway by estrogen or by 4-hydroxytamoxifen is coupled to estrogen receptor-induced apoptosis J. Biol. Chem. 275, 479-486, (2000) Abstract | |
| Obrero M, et al., Estrogen receptor-dependent and estrogen receptor-independent pathways for tamoxifen and 4-hydroxytamoxifen-induced programmed cell death J. Biol. Chem. 277, 45695-45703, (2002) Abstract | |
| Rabenoelina F, et al., Effect of prolonged hydroxytamoxifen treatment of MCF-7 cells on mitogen activated kinase cascade Int. J. Cancer 98, 698-706, (2002) Abstract | |
| Zhou JH, et al., Delayed and persistent ERK1/2 activation is required for 4-hydroxytamoxifen-induced cell death Steroids 72, 765-777, (2007) Abstract | |
| Aesoy R, et al., An autocrine VEGF/VEGFR2 and p38 signaling loop confers resistance to 4-hydroxytamoxifen in MCF-7 breast cancer cells Mol. Cancer Res. 6, 1630-1638, (2008) Abstract | |
| Kupfer, D., et al. Cancer Res. 54, 3140, (1994) | |
| Custodio, J.B.A., et al. Biochem. Pharmacol. 47, 1989, (1994) | |
| Manns, J.E., et al. Anal. Proc. 30, 161, (1993) | |
| Murphy, C.S., et al. Mol. Pharmacol. 38, 737, (1991) |
