Ixabepilone

CAT#: H201610

CAS#: 219989-84-1

Description: 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.

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Synthetic Routes

Ixabepilone - Synthetic Route 1

Ixabepilone route01

Synthetic reference

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

Ixabepilone - Synthetic Route 2

Ixabepilone route02

Synthetic reference

Process for the manufacture of ixabepilone; Haddad, Jalal; Nadji, Sourena; Assignee Pharmaren, LLC, USA; 2018; Patent Information; Mar 15, 2018; US 20180072749 A1

Ixabepilone - Synthetic Route 3

Ixabepilone route03

Synthetic reference

Process for the preparation of ixabepilone, and intermediates thereof; Chen, Yue; Hsiao, Tsung Yu; Henschke, Julian P.; Assignee ScinoPharm Taiwan, Ltd., Taiwan; 2014; Patent Information; Sep 11, 2014; US 20140256952 A1

Ixabepilone - Synthetic Route 4

Ixabepilone route04

Synthetic reference

Thirumalai Rajan, Srinivasan; Eswaraiah, Sajja; Reddy, Ghojala Venkat. Process for the preparation of (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione and intermediates thereof. Assignee MSN Laboratories Private Limited, India. WO 2015087351. (2015).

Ixabepilone - Synthetic Route 5

Ixabepilone route05

Synthetic reference

Wang, Dagui; Zhang, Xiaoyong; Tian, Xiaoyan; Yan, Jiaqi. Total synthesis of Ixabepilone and its analogue. Assignee Shenzhen JATIE Pharmaceutical Co., Ltd., Peop. Rep. China. CN 103275091. (2013).

Ixabepilone - Synthetic Route 6

Ixabepilone route06

Synthetic reference

Borzilleri, Robert M.; Zheng, Xiaoping; Schmidt, Robert J.; Johnson, James A.; Kim, Soong-Hoon; DiMarco, John D.; Fairchild, Craig R.; Gougoutas, Jack Z.; Lee, Francis Y. F.; Long, Byron H.; Vite, Gregory D. A Novel Application of a Pd(0)-Catalyzed Nucleophilic Substitution Reaction to the Regio- and Stereoselective Synthesis of Lactam Analogues of the Epothilone Natural Products. Journal of the American Chemical Society. Volume 122. Issue 37. Pages 8890-8897. 2000.