65213-48-1

Basic information

• Product Name: (Z)-4-HYDROXYTAMOXIFEN
• Synonyms: 4-OH-TAM;TAMOXIFEN, (Z)-4-HYDROXY-;TAMOXIFEN, 4-HYDROXY-, (Z)-;(Z)-4-HYDROXYTAMOXIFEN;(Z)-4-[1-[4-[2-(DIMETHYLAMINO)ETHOXY]PHENYL]-2-PHENYL-1-BUTENYL-PHENOL;(Z)-4-[1-(P-(DIMETHYLAMINOETHOXY)PHENYL)-2-PHENYL-1-BUTENYL]PHENOL;[Z]-1-[P-DIMETHYLAMINOETHOXYPHENYL]-1,2-DIPHENYL-1-BUTEN-4-OL;(Z)-1-(4-Hydroxyphenyl)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-butene
• CAS NO: 65213-48-1
• Molecular Formula: C26H29NO2
• Molecular Weight: 387.51
• Mol File: 65213-48-1.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 514.4°C at 760 mmHg
• Flash Point: 264.9°C
• Appearance: white/powder
• Density: 1.092g/cm³
• Vapor Pressure: 3.35E-11mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: 2-8°C
• Solubility: 95% ethanol: 20 mg/mL
• Stability: Light Sensitive
• CAS DataBase Reference: (Z)-4-HYDROXYTAMOXIFEN(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4-HYDROXYTAMOXIFEN(65213-48-1)
• EPA Substance Registry System: (Z)-4-HYDROXYTAMOXIFEN(65213-48-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-63
• Safety Statements: 22-23-36
• WGK Germany: 3
• RTECS: SL1210000
• Hazardous Substances Data: 65213-48-1(Hazardous Substances Data)

Usage

Description

(Z)-4-HYDROXYTAMOXIFEN, also known as (Z)-4-Hydroxy Tamoxifen, is a metabolite of Tamoxifen, a well-known drug used in the treatment of certain types of cancer. It is a hydroxylated analogue of Tamoxifen, which means it has an additional hydroxyl group attached to its molecular structure. This modification gives (Z)-4-HYDROXYTAMOXIFEN its unique properties, including anti-estrogenic effects.

Uses

Used in Pharmaceutical Industry:
(Z)-4-HYDROXYTAMOXIFEN is used as a pharmaceutical compound for its anti-estrogenic properties. It is particularly relevant in the treatment of hormone receptor-positive breast cancer, as it can help block the effects of estrogen, a hormone that can promote the growth of some breast cancers.
Additionally, due to its metabolite status, (Z)-4-HYDROXYTAMOXIFEN may be used in research and development to better understand the mechanisms of action and potential side effects of Tamoxifen, potentially leading to the development of improved treatments for various conditions.
Used in Research and Development:
(Z)-4-HYDROXYTAMOXIFEN is used as a research tool for studying the effects of Tamoxifen and its metabolites on cellular processes and signaling pathways. This can help scientists gain a deeper understanding of the drug's mode of action, as well as identify potential new targets for therapeutic intervention in cancer and other diseases.

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

• 91221-46-4 1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 93-55-0 1-phenyl-propan-1-one 
• 10540-29-1 tamoxifen 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 1361392-98-4 uridine 3'-(4-hydroxytamoxifen phosphate) 
• 115499-97-3 4-(methoxymethoxy)-4'-methoxybenzophenone 
• 124-40-3 dimethyl amine 
• 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 

Relevant articles and documents

Synthesis of Tamoxifen-Artemisinin and Estrogen-Artemisinin Hybrids Highly Potent Against Breast and Prostate Cancer

In the search for new and effective treatments of breast and prostate cancer, a series of hybrid compounds based on tamoxifen, estrogens, and artemisinin were successfully synthesized and analyzed for their in vitro activities against human prostate (PC-3) and breast cancer (MCF-7) cell lines. Most of the hybrid compounds exhibit a strong anticancer activity against both cancer cell lines – for example, EC50 (PC-3) down to 1.07 μM, and EC50 (MCF-7) down to 2.08 μM – thus showing higher activities than their parent compounds 4-hydroxytamoxifen (afimoxifene, 7; EC50=75.1 (PC-3) and 19.3 μM (MCF-7)), dihydroartemisinin (2; EC50=263.6 (PC-3) and 49.3 μM (MCF-7)), and artesunic acid (3; EC50=195.1 (PC-3) and 32.0 μM (MCF-7)). The most potent compounds were the estrogen-artemisinin hybrids 27 and 28 (EC50=1.18 and 1.07 μM, respectively) against prostate cancer, and hybrid 23 (EC50=2.08 μM) against breast cancer. These findings demonstrate the high potential of hybridization of artemisinin and estrogens to further improve their anticancer activities and to produce synergistic effects between linked pharmacophores.

New approach based on immunochemical techniques for monitoring of selective estrogen receptor modulators (SERMs) in human urine

Antiestrogenic compounds such as tamoxifen, toremifen and chlomifen are used illegally by athletes to minimize physical impacts such as gynecomastia resulting from the secondary effects of anabolic androgenic steroids, used to increase athletic efficiency unlawfully. The use of these compounds is banned by the World Anti-Doping Agency (WADA) and controls are made through analytical methodologies such as HPLC–MS/MS, which do not fulfil the sample throughput requirements. Moreover, compounds such as tamoxifen are also used to treat hormone receptor-positive breast cancer (ER +).Therapeutic drug monitoring (TDM) of tamoxifen may also be clinically useful for guiding treatment decisions. An accurate determination of these drugs requires a solid phase extraction of patient serum followed by HPLC–MS/MS. In the context of an unmet need of high-throughput screening (HTS) and quantitative methods for antiestrogenic substances we have approached the development of antibodies and an immunochemical assay for the determination of these antiestrogenic compounds. The strategy applied has taken into consideration that these drugs are metabolized and excreted in urine as the corresponding 4-hydroxylated compounds. A microplate-based ELISA procedure has been developed for the analysis of these metabolites in urine with a LOD of 0.15, 0.16 and 0.63 μg/L for 4OH-tamoxifen, 4OH-toremifen and 4OH-clomifen, respectively, much lower than the MRPL established by WADA (20 μg/L).

ANTICANCER AGENT DELIVERY MOLECULE

PROBLEM TO BE SOLVED: To provide a compound which can be used as an anticancer agent targeting a cancer cell that highly expresses Lysine-specific demethylase 1 (LSD1) or salt thereof. SOLUTION: The present invention provides a compound represented by the following formula (I) or a pharmaceutically acceptable salt thereof, where Ar, R1, R2, L, Z, p, q, *1 and *2 are as defined in the specifications. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT