H6278

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H6278

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4-Hydroxytamoxifen

Minimum 70% of Z isomer (remainder primarily E-isomer)

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:24895736

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Description

Biochem/physiol ActionsThe trans (Z) isomer has efficacy against estrogen-sensitive cancers. The cis (E) isomer is an estrogen agonist.
 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 descriptionMetabolite of the chemotherapeutic drug tamoxifen, exhibiting more potent estrogen agonist/antagonist activity than the parent drug. While the cis (E) isomer is an estrogen agonist, the trans (Z) isomer has efficacy against estrogen-sensitive cancers. Also active as intra-membranous inhibitor of lipid peroxidation.

Properties

assay≥98% (HPLC)
Gene Informationhuman ... ESR1(2099), ESR2(2100), ESRRG(2104), IL6(3569)
 rat ... Ar(24208), Esr1(24890), Esr2(25149)
storage temp.2-8°C

Safety

Personal Protective Equipmentdust mask type N95 (US), Eyeshields, Gloves
Hazard CodesXn
Risk Statements20/21/22-63
Safety Statements22-23-36
WGK Germany3
RTECSSL1210000

References

referenceMcCague R, et al., Nonisomerizable analogues of (Z)- and (E)-4-hydroxytamoxifen; Synthesis and endocrinological properties of substituted diphenylbenzocycloheptenes J. Med. Chem. 31, 1285-1290, (1988) Abstract
 Osborne CK, et al., Acquired tamoxifen resistance: correlation with reduced breast tumor levels of tamoxifen and isomerization of trans-4-hydroxytamoxifen J. Natl. Cancer Inst. 83, 1477-1482, (1991) Abstract
 Osborne CK, et al., Tamoxifen and the isomers of 4-hydroxytamoxifen in tamoxifen-resistant tumors from breast cancer patients J. Clin. Oncol. 10, 304-310, (1992) Abstract
 Yu DD, and Forman BM., Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator J. Org. Chem. 68, 9489-9491, (2003) Abstract
 Zheng Y, et al., Elimination of antiestrogenic effects of active tamoxifen metabolites by glucuronidation Drug Metab. Dispos. 35, 1942-1948, (2007) 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)