174592-47-3

Basic information

• Product Name: (E)-4-Hydroxytamoxifen
• Synonyms: (E)-4-Hydroxytamoxifen;cis-4-Hydroxy Tamoxifen Discontinued;4-[(1E)-1-[4-[2-(DiMethylaMino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol
• CAS NO: 174592-47-3
• Molecular Formula: C₂₆H₂₉NO₂
• Molecular Weight: 387.52
• Product Categories: Aromatics;Drug Analogues;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Aromatics, Drug Analogues, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 174592-47-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 514.4°C at 760 mmHg
• Flash Point: 264.9°C
• Appearance: /
• Density: 1.092g/cm³
• Vapor Pressure: 3.35E-11mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform
• CAS DataBase Reference: (E)-4-Hydroxytamoxifen(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-Hydroxytamoxifen(174592-47-3)
• EPA Substance Registry System: (E)-4-Hydroxytamoxifen(174592-47-3)

Safety Data

• Hazardous Substances Data: 174592-47-3(Hazardous Substances Data)

Usage

Description

(E)-4-Hydroxytamoxifen is a metabolite of Tamoxifen, a hydroxylated analogue with anti-estrogenic properties. It is derived from Tamoxifen through metabolic processes and exhibits similar pharmacological actions, playing a crucial role in the treatment of hormone-dependent cancers.

Uses

Used in Pharmaceutical Industry:
(E)-4-Hydroxytamoxifen is used as an active pharmaceutical ingredient for the development of medications targeting hormone-dependent cancers, such as breast cancer. Its anti-estrogenic properties help in blocking the effects of estrogen, a hormone that can promote the growth of certain cancer cells.
Used in Cancer Treatment:
(E)-4-Hydroxytamoxifen is used as a therapeutic agent for the treatment of hormone-dependent cancers, particularly breast cancer. It works by competing with estrogen for binding to its receptors, thereby inhibiting the growth and proliferation of cancer cells that rely on estrogen for survival and growth.
Used in Research Applications:
(E)-4-Hydroxytamoxifen is used as a research tool in the study of estrogen receptor signaling pathways and the development of novel anti-estrogenic drugs. Its structural and functional similarities to Tamoxifen make it a valuable compound for investigating the mechanisms of estrogen-dependent cancers and identifying potential therapeutic targets.

InChI:InChI=1/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+

Upstream product

• 103628-14-4 (Z)-1-<4-(2-chloroethoxy)phenyl>-1-<4-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>phenyl>-2-phenyl-1-butene 
• 124-40-3 dimethyl amine 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 93-55-0 1-phenyl-propan-1-one 
• 91221-46-4 1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 147323-02-2 E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene 
• 68047-06-3 Z-1-<4-(2-dimethylaminoethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene 
• 106-41-2 4-bromo-phenol 
• 36603-49-3 4-(tetrahydropyran-2'-yloxy)-1-bromobenzene 
• 622-86-6 2-chloroethoxybenzene 
• 108-95-2 phenol 
• 119757-57-2 (E,Z)-1-<4-(2-chloroethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene 
• 103628-22-4 1--2-phenyl-butan-1-one 

Relevant articles and documents

Simple and Efficient Production of (Z)-4-Hydroxytamoxifen, a Potent Estrogen Receptor Modulator

A McMurry coupling reaction and selective crystallization were used to develop a simple and efficient two-step synthesis of (Z)-4-hydroxytamoxifen (2a). This compound is an active metabolite of tamoxifen, a selective estrogen receptor (ER) modulator widely used to treat breast cancer. The synthesis employed 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene (1) as a useful building block.

TARGETED DRUG-FORMALDEHYDE CONJUGATES AND METHODS OF MAKING AND USING THE SAME

The invention provides a prodrug platform technology for improving the therapeutic value of a variety of parent drug compounds by altering and improving drug characteristics such as aqueous solubility, hydrolytic stability, therapeutic index, toxicity profile, pharmacokinetics and selectivity while allowing the potential for synthetic elaboration. The prodrug platform is particularly well suited for targeting therapeutic drugs, including anti-tumor drugs and antibiotics, to specific receptors on target cells (e.g., cancer cells and bacteria). The platform is a technology for providing an improved, preactivated form of a therapeutic drug, and for optionally targeting such drug to target cells or biological molecules. The invention is broadly applicable to many different therapeutic drugs, as well as to a variety of diseases and conditions, including a variety of forms of cancer and bacterial infections.

Synthesis and Sulfatase Inhibitory Activities of (E)- and (Z)-4-Hydroxytamoxifen Sulfamates

We report the development of (E)- and (Z)-4-hydroxytamoxifen sulfamates as estrone sulfatase inhibitors, potential therapeutic agents for the treatment of breast cancer. Both compounds competitively inhibit estrone sulfatase isolated from rat liver with apparent Ki of 35.9 μM for (E)-4-hydroxytamoxifen sulfamate and an apparent Ki of >500 μM for the (Z) isomer.