ChemicalBook CAS DataBase List IXABEPILONE

IXABEPILONE synthesis

9synthesis methods

Product Name:IXABEPILONE
CAS Number:219989-84-1
Molecular formula:C27H42N2O5S
Molecular Weight:506.7

Ixabepilone (also known as azaepothilone B, or BMS-247550) is an orally bioavailable microtubule inhibitor. Ixabepilone was a semisynthetic analogue of epothilone B with antineoplastic activity. Ixabepilone binds to tubulin and promotes tubulin polymerization and microtubule stabilization, thereby arresting cells in the G2-M phase of the cell cycle and inducing tumor cell apoptosis. This agent demonstrates antineoplastic activity against taxane-resistant cell lines. Ixabepilone was approved in 2007.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

Synthesis of epothilones, intermediates and analogs for use in treatment of cancers with multidrug resistant phenotype; Danishefsky, Samuel J.; Lee, Chul Bom; Chappell, Mark; Stachel, Shawn; Chou, Ting-chao; Assignee Sloan-Kettering Institute for Cancer Research, USA; 2001; Patent Information; Sep 07, 2001; WO 2001064650 A2

152044-54-7 Synthesis