Tuesday, January 27, 2015


Common name: Decitabine; Dacogen; 5-Aza-2'-deoxycytidine; Dezocitidine; 5-Azadeoxycytidine; Azadc
Trademarks:  Dacogen
Molecular Formula: C8H12N4O4
CAS Registry Number: 2353-33-5
CAS Name: 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
Molecular Weight: 228.206
SMILES: NC1=NC(=O)N(C=N1)[C@H]1C[C@H](O)[C@@H](CO)O1
InChI: InChI=1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1
Activity: Acute Myeloid Leukemia Therapy; AML Therapy; Treatment of Myelodysplastic Syndromes; DNA Methyltransferase Inhibitor; Enzyme Inhibitor; Antimetabolites; Antineoplastic; Oncolytic Drugs; Leukemia Therapy
Status: Launched 2006
Originator: Pharmachemie/SuperGen (Licensee)

Decitabine synthesis: WO2008101448A2 (Piskala's patent)

Decitabine synthesis: Collect Czech Chem Commun 1964, 29, 2576-2577 (The very first reported synthesis. Authors have not separated anomers.)

1. Henschke, J. P.; et. al. Synthesis of Decitabine. US20100087637 (cites many synthetic routes)
2. Piskala, A.; et. al. Method of manufacturing 1-(2-deoxy-alpha-d-erythro-pentofuranosyl)-5-azacytosine. WO2008101448A2
3. Li, J. J.; Johnson, D. S. Modern Drug Synthesis. 2010 Wiley publications (caution: they have reported wrong patent number, WO 08101445 instead of WO 08101448)
4. Jabbour, E.; et. al. Evolution of decitabine development: accomplishments, ongoing investigations, and future strategies. Cancer 2008, 112(11), 2341-2351. (activity)
5. Daskalakis, M.; et. al. Decitabine. Recent Results Cancer Res 2010, 184, 131-157. (activity)
4. Piskala, A.; et. al. Synthesis of a 2-deoxy-d-ribofuranosyl-s-azacytosine. Collect Czech Chem Commun 196429, 2576-2577.