Decitabine

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Decitabine
Decitabine.svg
Systematic (IUPAC) name
4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one
Clinical data
Trade names Dacogen
AHFS/Drugs.com monograph
MedlinePlus a608009
Pregnancy cat.
  • D
Legal status
  • Prescription only
Routes Intravenous
Pharmacokinetic data
Protein binding <1%
Half-life 30 minutes
Identifiers
CAS number 2353-33-5 YesY
ATC code L01BC08
PubChem CID 451668
DrugBank DB01262
ChemSpider 397844 YesY
UNII 776B62CQ27 YesY
KEGG D03665 YesY
ChEBI CHEBI:50131 YesY
ChEMBL CHEMBL1201129 N
Chemical data
Formula C8H12N4O4 
Mol. mass 228.206 g/mol
 N (what is this?)  (verify)

Decitabine (trade name Dacogen), or 5-aza-2'-deoxycytidine, is a drug for the treatment of myelodysplastic syndromes, a class of conditions where certain blood cells are dysfunctional, and for acute myeloid leukemia (AML).[1] Chemically, it is a cytidine analog.

Mechanism[edit]

Decitabine is a hypomethylating agent.[2][3] It hypomethylates DNA by inhibiting DNA methyltransferase.

It functions in a similar manner to azacitidine, although decitabine can only be incorporated into DNA strands while azacitidine can be incorporated into both DNA and RNA chains.

Clinical uses[edit]

Decitabine is indicated for the treatment of myelodysplastic syndromes (MDS) including previously treated and untreated, de novo and secondary MDS of all French-American-British subtypes (refractory anemia, refractory anemia with ringed sideroblasts, refractory anemia with excess blasts, refractory anemia with excess blasts in transformation, and chronic myelomonocytic leukemia) and Intermediate-1, Intermediate-2, and High-Risk International Prognostic Scoring System groups. In patients with renal insufficiency, Batty and colleagues reported the first case series on the feasibility of therapy with hypomethylating agents in patients with renal insufficiency.[4]

Chemical synthesis[edit]

Decitabine can be synthesized from a benzoyl-protected chlorosugar:[5] Decitabine.png

References[edit]

  1. ^ "EC Approves Marketing Authorization Of DACOGEN For Acute Myeloid Leukemia". 2012-09-28. Retrieved 28 September 2012. 
  2. ^ Kantarjian H, Issa JP, Rosenfeld CS, et al. (April 2006). "Decitabine improves patient outcomes in myelodysplastic syndromes: results of a phase III randomized study". Cancer 106 (8): 1794–1803. doi:10.1002/cncr.21792. PMID 16532500. 
  3. ^ Kantarjian HM, O'Brien S, Cortes J, et al. (August 2003). "Results of decitabine (5-aza-2'deoxycytidine) therapy in 130 patients with chronic myelogenous leukemia". Cancer 98 (3): 522–528. doi:10.1002/cncr.11543. PMID 12879469. 
  4. ^ Ravandi, F.; Kantarjian, J. E.; Issa, S.; Jabbour, S.; Santos, G.; McCue, D.; Garcia-Manero, F. P. S.; Pierce, E.; O'Brien, J. P.; Cortés, J. E.; Ravandi, F. (2010). "Feasibility of Therapy with Hypomethylating Agents in Patients with Renal Insufficiency". Clinical Lymphoma, Myeloma & Leukemia 10 (3): 205–210. doi:10.3816/CLML.2010.n.032. PMC 3726276. PMID 20511166.  edit
  5. ^ Piml, J.; Sorm, F. (1964). Coll. Czech. Chem. Commun. 29: 2576. 

Further reading[edit]

External links[edit]