4Hydroxy Tamoxifen Chemical Properties

Melting point:

150-153°C

Boiling point:

514.4±50.0 °C(Predicted)

Density 

1.092±0.06 g/cm3(Predicted)

storage temp. 

Amber Vial, -20°C Freezer, Under Inert Atmosphere

solubility 

Chloroform (Slightly), Dichloromethane, Methanol (Slightly)

form 

Solid

pka

10.32±0.15(Predicted)

color 

White to Off-White

Stability:

Light Sensitive

4Hydroxy Tamoxifen Usage And Synthesis

Description

4’-hydroxy Tamoxifen is one of five main phase I metabolites of tamoxifen , a well-known estrogen receptor antagonist in breast but partial estrogen receptor agonist in endometrium. 4’-hydroxy Tamoxifen is a product of cytochrome P450 (CYP)2D6 and CYP2B6 activity. With the addition of a hydroxyl group, 4’-hydroxy tamoxifen has been shown to have a higher affinity for estrogen receptors compared to tamoxifen. At 10-100 μM, 4’-hydroxy tamoxifen is cytotoxic, in a non-apoptotic manner, to HEC-1B and HEC-1A human endometrial adenocarcinoma cell lines.

Chemical Properties

White Solid

Uses

A metabolite of Tamoxifen (T006000).

References

[1] ROLAND L?SER . In vivo and in vitro antiestrogenic action of 3-hydroxytamoxifen, tamoxifen and 4-hydroxytamoxifen[J]. European Journal of Cancer and Clinical Oncology, 1985, 21 8: Pages 985-990. DOI: 10.1016/0277-5379(85)90119-1
[2] H KIM CREWE. Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4’-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen.[J]. Drug Metabolism and Disposition, 2002, 32 1: 869-874. DOI: 10.1124/dmd.30.8.869
[3] H SEEGER. Inhibition of human breast cancer cell proliferation with estradiol metabolites is as effective as with tamoxifen.[J]. Hormone and Metabolic Research, 2004, 36 5: 277-280. DOI: 10.1055/s-2004-814480
[4] MARIA E CUEVAS  Tracey E L. In vitro cytotoxicity of 4’-OH-tamoxifen and estradiol in human endometrial adenocarcinoma cells HEC-1A and HEC-1B.[J]. Oncology reports, 2015, 33 1: 464-470. DOI: 10.3892/or.2014.3565
[5] GIORGIA URBINATI. Therapeutic potential of new 4-hydroxy-tamoxifen-loaded pH-gradient liposomes in a multiple myeloma experimental model.[J]. Pharmaceutical Research, 2010, 27 2: 327-339. DOI: 10.1007/s11095-009-0023-z

4Hydroxy Tamoxifen(82413-23-8)Related Product Information

• (E/Z)-Tamoxifen
• N-Desmethyl-4-hydroxy Tamoxifen (approx. 1:1 E/Z Mixture)
• Tamoxifen Impurity 3
• 4-Benzyloxy β-Hydroxy TaMoxifen
• TaMoxifen DiMer
• 1-(4-(2-Dimethylamino)-2-ethoxyphenyl butanone
• N-Desmethyl-4-hydroxy Tamoxifen β-D-Glucuronide (E/Z Mixture)
• Tamoxifen EP Impurity D
• (E)-4-Alloxycarboxyl Tamoxifen
• desdimethyltamoxifen
• TAMOXIFEN-N-OXIDE
• Droloxifene
• (E)-4-Acetoxy Tamoxifen
• N-Desmethyl Tamoxifen Methanethiosulfonate
• 2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethyl-ethanamine
• alpha-[4-[2-(dimethylamino)ethoxy]phenyl]-beta-ethyl-alpha-phenylphenethyl alcohol
• (E)-4-Hydroxy-N-desmethyl Tamoxifen
• Avacopan