Azacitidine

CAT#: H100070

CAS#: 320-67-2

Description: Azacitidine is a pyrimidine nucleoside analogue of cytidine with antineoplastic activity. Azacitidine is incorporated into DNA, where it reversibly inhibits DNA methyltransferase, thereby blocking DNA methylation. Hypomethylation of DNA by azacitidine may activate tumor suppressor genes silenced by hypermethylation, resulting in an antitumor effect. This agent is also incorporated into RNA, thereby disrupting normal RNA function and impairing tRNA cytosine-5-methyltransferase activity.

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Synthetic Routes

Azacitidine - Synthetic Route 1

Azacitidine route01

Synthetic reference

Vujjini, Satish Kumar; Varanasi, Ganesh; Arevelli, Srinivas; Kandala, Sreenatha Charyulu; Tirumalaraju, Satyanarayana Raju; Bandichhor, Rakeshwar; Kagga, Mukkanti; Cherukupally, Praveen. An Improved and Scalable Process for the Synthesis of 5-Azacytidine: An Antineoplastic Drug. Organic Process Research & Development. API-Research and Development, Integrated Product Development. Dr. Reddy's Laboratories Ltd. Bachupally, India 500072. Volume 17. Issue 2. Pages 303-306. 2013

Azacitidine - Synthetic Route 2

Azacitidine route02

Synthetic reference

Bozhok, T. S.; Kalinichenko, E. N.; Kuz'mitskii, B. B.; Golubeva, M. B. Synthesis, Hydrolytic Stability, and Antileukemic Activity of Azacytidine Nucleoside Analogs. Pharmaceutical Chemistry Journal. Institute of Bioorganic Chemistry. National Academy of Sciences of Belarus. Minsk, Belarus 220141. Volume 49. Issue 12. Pages 804-809. 2016

Azacitidine - Synthetic Route 3

Azacitidine route03

Synthetic reference

Guo, Gang; Yang, Qianjiao; Zhao, Lihui; Liu, Dan; Zhao, Linxiang. Improved synthesis of azacytidine. Zhongguo Yaowu Huaxue Zazhi. School of Pharmaceutical Engineering. Shenyang Pharmaceutical University. Shenyang, Liaoning Province, Peop. Rep. China 110016. Volume 18. Issue 5. Pages 377-378, 383. 2008

Azacitidine - Synthetic Route 4

Azacitidine route04

Synthetic reference

Daifuku, Richard; Gall, Alexander; Sergueev, Dmitri. Treatment of viral diseases by 1,3,5-triazine nucleoside and nucleotide analogs, and preparation thereof. Assignee Koronis Pharmaceuticals, Incorporated, USA. WO 2004028454. 2004

Azacitidine - Synthetic Route 5

Azacitidine route05

Synthetic reference

Cherukupally, Praveen; Vujjini, Satish Kumar; Varanasi, Ganesh; Kandala, Sreenadha Charyulu; Areveli, Srinivas; Tirumalaraju, Satyanarayana Raju. Azacytidine process and polymorphs. Assignee Dr. Reddy's Laboratories Ltd., India; Dr. Reddy's Laboratories, Inc. WO 2010014883. 2010

Azacitidine - Synthetic Route 6

Azacitidine route06

Synthetic reference

Yao, Quanxing; Li, Jing; Yang, Junbo. Method for synthesizing azacytidine from hexamethyldisilazane and 5-azacytosine. Assignee Chongqing Taihao Pharmaceutical Co., Ltd., Peop. Rep. China. CN 101974051. 2011

Azacitidine - Synthetic Route 7

Azacitidine route07

Synthetic reference

Liu, Guanghai; Jin, Xiaomin. Process for preparation of azacitidine. Assignee Huzhou Zhanwang Pharmaceutical Co., Ltd., Peop. Rep. China. CN 102702292. 2012

Azacitidine - Synthetic Route 8

Azacitidine route08

Synthetic reference

Ionescu, Dumitru; Blumbergs, Peter. Synthesis of 5-azacytidine via ribosylation of azacytosine. Assignee Pharmion Corporation, USA. US 20040186283. 2004

Azacitidine - Synthetic Route 9

Azacitidine route09

Synthetic reference

Bigatti, Ettore; Lux, Giovanna; Paiocchi, Maurizio; Giolito, Andrea; Tosi, Simone. Process for preparing azacytidine intermediates. Assignee Sicor Inc., USA. WO 2010017374. 2010