CAS 174592-47-3

(E)-4-Hydroxytamoxifen

Description:

(E)-4-Hydroxytamoxifen is a selective estrogen receptor modulator (SERM) primarily used in the treatment of estrogen receptor-positive breast cancer. It is a derivative of tamoxifen, featuring a hydroxyl group at the 4-position of the ethylene bridge, which enhances its anti-estrogenic activity. This compound exhibits a unique ability to bind to estrogen receptors, modulating their activity depending on the target tissue. In breast tissue, it acts as an antagonist, inhibiting estrogen-driven tumor growth, while in other tissues, it may exhibit estrogen-like effects. The substance is characterized by its relatively high lipophilicity, which influences its pharmacokinetics and bioavailability. Its chemical structure includes a phenolic group, contributing to its biological activity. (E)-4-Hydroxytamoxifen is often administered orally and is known for its side effects, which can include hot flashes, nausea, and an increased risk of thromboembolic events. Overall, it plays a crucial role in breast cancer therapy, particularly in pre- and post-menopausal women.

Formula: C₂₆H₂₉NO₂

InChI: 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: InChIKey=TXUZVZSFRXZGTL-OCEACIFDSA-N

SMILES: C(=C(\CC)/C1=CC=CC=C1)(\C2=CC=C(OCCN(C)C)C=C2)/C3=CC=C(O)C=C3

Synonyms:

• (E)-4-[1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenylbut-1-en-1-yl]phenol
• 4-[(1E)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol
• 4-[(1E)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]phenol
• 4-[(1E)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol
• Cis-4-Hydroxytamoxifen
• Phenol, 4-(1-(4-(2-(Dimethylamino)Ethoxy)Phenyl)-2-Phenyl-1-Butenyl)-,
• Phenol, 4-[(1E)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]-
• Phenol, 4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]-, (E)-
• phenol, 4-[(1E)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-
• trans-4-(1-(4-(2-(Dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)phenol

(E)-4-Hydroxytamoxifen

CAS: 174592-47-3

(E)-4-Hydroxytamoxifen is a less active isomer of (Z)-4-hydroxytamoxifen and also is an estrogen receptor modulator.

Formula: C₂₆H₂₉NO₂

Color and Shape: Solid

Molecular weight: 387.51

Ref: TM-T15186

(E)-4-Hydroxy Tamoxifen

CAS: 174592-47-3

Formula: C₂₆H₂₉NO₂

Molecular weight: 387.52

Ref: 4Z-T-0140

(E)-4-Hydroxy Tamoxifen-d5 (Contains up to 10% Z isomer)

Controlled Product

CAS: 174592-47-3

Applications (E)-4-Hydroxy Tamoxifen-d5 is an labelled metabolite of Tamoxifen (T006000). A hydroxylated analogue of Tamoxifen with anti-estrogenic properties.
References Muerdter, T.E., et al.: Clin. Pharmacol. Therapeut., 89, 708 (2011); Dorchies, O. M., et al.: Am. J. Pathol., 182, 485 (2013);

Formula: C₂₆H₂₄D₅NO₂

Color and Shape: Neat

Molecular weight: 392.54

Ref: TR-H954772

4-Hydroxy Tamoxifen-d5 (E/Z Mixture)

Controlled Product

CAS: 174592-47-3

Formula: C₂₆H₂₄D₅NO₂

Color and Shape: Neat

Molecular weight: 392.54

Ref: TR-H954771

(E)-4-Hydroxy tamoxifen

Controlled Product

CAS: 174592-47-3

(E)-4-Hydroxy tamoxifen is a drug that binds to the estrogen receptor and inhibits its ability to bind to DNA. It binds specifically to the response element of the gene for estrogen receptor. (E)-4-Hydroxy tamoxifen has been shown to have anti-cancer effects in breast cancer cells, but does not affect healthy cells. The drug also has a high affinity for skin tumors, where it causes an increase in cell proliferation and inhibits apoptosis. This drug is also used as a marker for chromatographic analysis of tamoxifen and 4-hydroxytamoxifen in biological samples.

Formula: C₂₆H₂₉NO₂

Purity: Min. 95%

Molecular weight: 387.51 g/mol

Ref: 3D-FH158367