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 namesDacogen
AHFS/Drugs.commonograph
MedlinePlusa608009
Pregnancy cat.D
Legal status Prescription only
RoutesIntravenous
Pharmacokinetic data
Protein binding<1%
Half-life30 minutes
Identifiers
CAS number2353-33-5 YesY
ATC codeL01BC08
PubChemCID 451668
DrugBankDB01262
ChemSpider397844 YesY
UNII776B62CQ27 YesY
KEGGD03665 YesY
ChEBICHEBI:50131 YesY
ChEMBLCHEMBL1201129 N
Chemical data
FormulaC8H12N4O4 
Mol. mass228.206 g/mol
 N (what is this?)  (verify)
 
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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 namesDacogen
AHFS/Drugs.commonograph
MedlinePlusa608009
Pregnancy cat.D
Legal status Prescription only
RoutesIntravenous
Pharmacokinetic data
Protein binding<1%
Half-life30 minutes
Identifiers
CAS number2353-33-5 YesY
ATC codeL01BC08
PubChemCID 451668
DrugBankDB01262
ChemSpider397844 YesY
UNII776B62CQ27 YesY
KEGGD03665 YesY
ChEBICHEBI:50131 YesY
ChEMBLCHEMBL1201129 N
Chemical data
FormulaC8H12N4O4 
Mol. mass228.206 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. ^
    1. REDIRECT Template:Cite pmid
  5. ^ Piml, J.; Sorm, F. (1964). Coll. Czech. Chem. Commun. 29: 2576. 

Further reading[edit]

External links[edit]