116057-75-1

Basic information

• Product Name: IDOXIFENE
• Synonyms: IDOXIFENE;(e)-1-(2-(4-(1-(4-iodophenyl)-2-phenyl-1-butenyl)phenoxy)ethyl)pyrrolidine;(e)-pyrrolidin;cb7432;iodoxifene;pyrrolidino-4-iodotamoxifen;(E)-1-[4-(2-(Pyrrolidin-1-yl)ethoxy)phenyl]-1-(4-iodophenyl)-2-phenyl-1-butene;1-[2-[4-[(1E)-1-(4-Iodophenyl)-2-phenyl-1-buten-1-yl]phenoxy]ethyl]pyrrolidine
• CAS NO: 116057-75-1
• Molecular Formula: C₂₈H₃₀INO
• Molecular Weight: 523.45
• Mol File: 116057-75-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 108-109° (McCague et al.)
• Boiling Point: 573.447 °C at 760 mmHg
• Flash Point: 300.61 °C
• Appearance: /
• Density: 1.329
• Vapor Pressure: 3.72E-13mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: 2-8°C
• PKA: 9.61±0.20(Predicted)
• CAS DataBase Reference: IDOXIFENE(CAS DataBase Reference)
• NIST Chemistry Reference: IDOXIFENE(116057-75-1)
• EPA Substance Registry System: IDOXIFENE(116057-75-1)

Safety Data

• Hazardous Substances Data: 116057-75-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 116057-75-1 differently. You can refer to the following data:
1. SERM for treatment of urogenital atrophy weak estrogen and antiestrogen in uterus
2. Idoxifene is a non-steroidal estrogen antagonist. It is structurally analogous to tamoxifen (T006000).

InChI:InChI=1/C28H30INO/c1-2-27(22-8-4-3-5-9-22)28(23-10-14-25(29)15-11-23)24-12-16-26(17-13-24)31-21-20-30-18-6-7-19-30/h3-5,8-17H,2,6-7,18-21H2,1H3/b28-27-

Upstream product

• 622-86-6 2-chloroethoxybenzene 
• 116057-72-8 1-[4-(2-Chloro-ethoxy)-phenyl]-1-(4-iodo-phenyl)-2-phenyl-butan-1-ol 
• 103628-22-4 1--2-phenyl-butan-1-one 
• 122-99-6 2-Phenoxyethanol 
• 123-75-1 pyrrolidine 
• 116057-73-9 (E)-1-<4-(2-chloroethoxy)phenyl>-1-(4-iodophenyl)-2-phenyl-1-butene 
• 90-27-7 2-Phenylbutyric acid 

Relevant articles and documents

Development of an efficient and stereoselective manufacturing route to idoxifene

A literature route to 1-(2-{4-[(E)-1-(4-iodophenyl)-2-phenyl-but-1-enyl]phenoxy}ethyl)pyrrolidine (idoxifene) has been modified to tackle various scale-up issues and provide initial supplies. A new highly efficient, robust, and stereoselective manufacturing route is described in detail. This route involves diastereoselective synthesis of tertiary alcohol (1RS,2SR)-1-(4-iodophenyl)-2-phenyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]butan- 1-ol by Grignard addition to the ketone 1-(4-iodophenyl)-2-phenyl-1-butanone followed by derivatisation and stereoselective syn elimination to provide idoxifene in excellent yield and geometric purity. Evaluation of a more direct route to idoxifene using a McMurry low-valent titanium coupling reaction is also described.

Derivatives of Tamoxifen. Dependence of Antiestrogenicity on the 4-Substituent

A range of tamoxifen derivatives substituted in the 4-position of the 1-phenyl ring are described.The key steps in the synthesis of 4-iodo-, 4-bromo-, and 4-(methylthio)tamoxifen were reactions of 1,2-diarylbutanones with the (4-halogenophenyl)lithium or magnesium bromide.Oxidized precursors of 4-(methylthio)tamoxifen were used to prepare the methylsulfinyl and methylsulfonyl derivatives.Further derivatives (formyl, hydroxymethyl, oxirane, mercapto) were prepared from 4-bromotamoxifen via the 4-lithio derivative.Several of the derivatives (Br, I, SMe, SoMe, SO2Me, oxirane, CHO, CH2OH) displayed a higher affinity for estrogen receptors (ER) of calf uterine cytosol than did tamoxifen, but there was no relationship between affinity to ER and the ability to inhibit the growth of the MCF-7 breast cancer cell line in vitro.