| Identification | Back Directory | [Name]
4-HYDROXYTAMOXIFEN | [CAS]
68047-06-3 | [Synonyms]
4-OHT
C05011
(Z)-4-OHT
ici79,280
hydroxytamoxifen
4-HYDROXYTAMOXIFEN
TAMOXIFEN, 4-HYDROXY-
cis-4-Hydroxytamoxifen
trans-4-Hydroxytamoxifen
See H9711, H9712, or H9716
TAMOXIFEN 4-HYDROXY, (E) AND (Z) ISOMERS (50:50)
4-(1-(4-(dimethylaminoethoxy)phenyl)-2-phenyl-1-butenyl)phenol
(Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol
(Z)-3,4-Diphenyl-4-[4-[2-(dimethylamino)ethoxy]phenyl]-3-buten-1-ol
4-[(E)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]phenol
trans-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)phenol
2-[4-[(E)-1-(4-Hydroxyphenyl)-2-phenyl-1-butenyl]phenoxy]-N,N-dimethylethanamine
N,N-Dimethyl-2-[4-[(E)-1-(4-hydroxyphenyl)-2-phenyl-1-butenyl]phenoxy]ethanamine
trans-4-Hydroxytamoxifen, (Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol | [Molecular Formula]
C26H29NO2 | [MDL Number]
MFCD00468090 | [MOL File]
68047-06-3.mol | [Molecular Weight]
387.51 |
| Chemical Properties | Back Directory | [Appearance]
Powder | [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 |
| Hazard Information | Back Directory | [Chemical Properties]
Powder | [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]
A hydroxylated analogue of tamoxifen with anti-estrogenic properties. A metabolite of Tamoxifen.
| [Uses]
A metabolite of Tamoxifen (T006000). A hydroxylated analogue of Tamoxifen with anti-estrogenic properties. | [Uses]
tamoxifen metabolite, anti-estrogen, see Tamoxifen 1,01038 | [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]
Store at -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. |
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