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H7904

(Z)-4-Hydroxytamoxifen

Name: (Z)-4-Hydroxytamoxifen
Brand: SIGMA

≥98% (HPLC), powder, estrogen receptor modulator

Synonym(s):

4OH-Tamoxifen, (Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol, (Z)-4-OHT, trans-4-Hydroxytamoxifen

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About This Item

Empirical Formula (Hill Notation):

C₂₆H₂₉NO₂

CAS Number:

68047-06-3

Molecular Weight:

387.51

MDL number:

MFCD00278780

UNSPSC Code:

51111800

PubChem Substance ID:

24895814

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

300

Storage condition:

desiccated, protect from light

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Properties

Product Name

(Z)-4-Hydroxytamoxifen, ≥98% Z isomer

Quality Level

300

assay

≥98% (HPLC)

form

powder

storage condition

desiccated, protect from light

solubility

methanol: 10 mg/mL, ethanol: 20 mg/mL (with heating)

antibiotic activity spectrum

neoplastics

mode of action

enzyme | inhibits

originator

AstraZeneca

storage temp.

2-8°C

SMILES string

CC\C(c1ccccc1)=C(/c2ccc(O)cc2)c3ccc(OCCN(C)C)cc3

InChI

1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-

InChI key

TXUZVZSFRXZGTL-QPLCGJKRSA-N

Gene Information

human ... ESR1(2099), ESR2(2100), ESRRG(2104), IL6(3569)
rat ... Ar(24208), Esr1(24890), Esr2(25149)

Description

General description

4-Hydroxytamoxifen (4-OHT) is a metabolite of the antiestrogen tamoxifen in humans and other mammals. Both the Z (trans) and E (cis) 4-OHT isomers exhibit antiestrogenic properties in immature rats. Studies on the structure-function relationships of fixed ring systems have revealed that the trans isomer is a potent antiestrogen, while the cis isomer is relatively weaker (about 100 times less potent) as an antiestrogen in T47D breast cancer cells in vitro. 4-OHT binds to estrogen receptors (ER) and estrogen-related receptors (ERR), exerting both estrogenic and anti-estrogenic effects. This compound is a cell-permeable, selective estrogen receptor modulator (SERM). Compared to tamoxifen and its other metabolites, 4-OHT demonstrates a higher affinity for binding to estrogen receptors, resulting in 50 to 100-fold greater potency in inhibiting cell proliferation in normal human breast cells and breast cancer cell lines in culture. Moreover, 4-OHT has been found effective in inhibiting the growth of these cells in the absence of estrogen when cell proliferation was induced by insulin or epidermal growth factor.

Application

(Z)-4-Hydroxytamoxifen has been used:

as a media supplement to study the cell viability by WST-1 Assay
for inducing deletion of transforming growth factor-β (TGF-β gene in mice
to induce Cre recombinase activity in vitro.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.