4-HYDROXYTAMOXIFEN Property

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

Hazard Codes 

Xn

Risk Statements 

20/21/22-63

Safety Statements 

22-23-36

WGK Germany 

3

RTECS 

SL1210000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H350May cause cancer

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

4-HYDROXYTAMOXIFEN Chemical Properties,Usage,Production

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.