4-HYDROXYTAMOXIFEN Chemical Properties

Melting point:

105-107°C

Boiling point:

513.45°C (rough estimate)

Density 

1.1005 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

2-8°C

solubility 

95% ethanol: 20 mg/mL

form 

powder

pka

10.35±0.15(Predicted)

color 

white

Stability:

Stable. Store cool. Incompatible with strong oxidizing agents.

InChIKey

TXUZVZSFRXZGTL-OCEACIFDSA-N

CAS DataBase Reference

68047-06-3

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-63

Safety Statements 

22-23-36

WGK Germany 

3

RTECS 

SL1210000

4-HYDROXYTAMOXIFEN Usage And Synthesis

Chemical Properties

Powder

Uses

A metabolite of Tamoxifen (T006000). A hydroxylated analogue of Tamoxifen with anti-estrogenic properties.

Uses

(Z)-4-Hydroxy Tamoxifen is a metabolite of Tamoxifen (T006000). (Z)-4-Hydroxy Tamoxifen is a hydroxylated analogue of Tamoxifen. (Z)-4-Hydroxy Tamoxifen is a metabolite of Tamoxifen with anti-estrogenic properties.

Uses

tamoxifen metabolite, anti-estrogen, see Tamoxifen 1,01038

Uses

A hydroxylated analogue of tamoxifen with anti-estrogenic properties. A metabolite of Tamoxifen.

Definition

ChEBI: Afimoxifene is a tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen. It has a role as an antineoplastic agent, an estrogen receptor antagonist and a metabolite. It is a tertiary amino compound and a member of phenols. It is functionally related to a tamoxifen.

General Description

A cell-permeable, active metabolite of Tamoxifen (Cat. No. 579000) that acts as a potent inhibitor of PKC. It is more potent than the parent compound and inhibits PKC by modifying its catalytic domain. Also available as a 10 mM solution in EtOH (Cat. No. 508225).

Biological Activity

estrogen receptors (er) are members of the superfamily of ligand-modulated nuclear receptors that mediate the actions of steroid hormones, vitamin d, retinoids, and thyroid hormones. er is activated in vivo when bound by naturally occurring estrogens such as 17α-estradiol. in addition to regulating these physiological processes, estrogen also plays a central role in stimulating breast cancer growth. (z)-tamoxifen is a first generation selective er modulators that is currently approved by the fda and is widely used to treat estrogen-dependent breast cancers. its active metabolite, (z)-4-hydroxytamoxifen, is a potent estrogen receptor modulator.

Biochem/physiol Actions

Cell permeable: yes

in vitro

(z)-4-hydroxytamoxifen binds to er with 8-fold higher affinity than tamoxifen. it was found that only the z isomer has the required antiestrogenic activity; the (e)-4-hydroxytamoxifen has only about 5% of its affinity for the er [1].

in vivo

the antioestrogenic activities of (z)-4-hydroxytamoxifen and tamoxifen were determined after oral administration. (z)-4-hydroxytamoxifen was administered to groups of immature rats which also received s.c. injections of 0-2 μg oestradiol. both compounds produced a dose-related decrease in uterine wet weight when compared with the oestradiol-treated controls. at a dose of 1 μg/day, the antiuterotrophic effects of (z)-4-hydroxytamoxifen and tamoxifen were not significantly different but at 5μg/day, (z)-4-hydroxytamoxifen was more active (p < 0.01). (z)-4-hydroxytamoxifen therefore appears to retain its potent antioestrogenic activity after oral administration [2].

storage

-20°C

References

[1] donna d. yu and barry m. forman. simple and efficient production of (z)-4-hydroxytamoxifen, a potent estrogen receptor modulator. j. org. chem. 2003, 68, 9489-9491
[2] jordan vc, collins mm, rowsby l, prestwich g. a monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity. j endocrinol. 1977 nov;75(2):305-16.

4-HYDROXYTAMOXIFEN(68047-06-3)Related Product Information

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