WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100250
CAS#: 2353-33-5
Description: Decitabine is a cytidine antimetabolite analogue with potential antineoplastic activity. Decitabine incorporates into DNA and inhibits DNA methyltransferase, resulting in hypomethylation of DNA and intra-S-phase arrest of DNA replication.
MedKoo Cat#: 100250
Name: Decitabine
CAS#: 2353-33-5
Chemical Formula: C8H12N4O4
Exact Mass: 228.08585
Molecular Weight: 228.2
Elemental Analysis: C, 42.10; H, 5.30; N, 24.55; O, 28.04
Synonym: 5-aza-dCyd; deoxyazacytidine; dezocitidine; US brand name: Dacogen. Abbreviations: 5AZA; DAC
IUPAC/Chemical Name: 4-amino-1-((2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one
InChi Key: XAUDJQYHKZQPEU-JKUQZMGJSA-N
InChi Code: 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
SMILES Code: O=C1N([C@H]2O[C@H](CO)[C@@H](O)C2)C=NC(N)=N1
Appearance: white solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, DMF, and PBS
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO or water
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 228.2 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Ganetsky A. The role of decitabine for the treatment of acute myeloid leukemia. Ann Pharmacother. 2012 Nov;46(11):1511-7. doi: 10.1345/aph.1R151. Epub 2012 Oct 31. Review. PubMed PMID: 23115225.
2: Joeckel TE, Lübbert M. Clinical results with the DNA hypomethylating agent 5-aza-2'-deoxycytidine (decitabine) in patients with myelodysplastic syndromes: an update. Semin Hematol. 2012 Oct;49(4):330-41. doi: 10.1053/j.seminhematol.2012.08.001. Review. PubMed PMID: 23079063.
3: Marks PW. Decitabine for acute myeloid leukemia. Expert Rev Anticancer Ther. 2012 Mar;12(3):299-305. doi: 10.1586/era.11.207. Review. PubMed PMID: 22369322.
4: Bryan J, Kantarjian H, Garcia-Manero G, Jabbour E. Pharmacokinetic evaluation of decitabine for the treatment of leukemia. Expert Opin Drug Metab Toxicol. 2011 May;7(5):661-72. doi: 10.1517/17425255.2011.575062. Review. PubMed PMID: 21500965.
5: Cowan LA, Talwar S, Yang AS. Will DNA methylation inhibitors work in solid tumors? A review of the clinical experience with azacitidine and decitabine in solid tumors. Epigenomics. 2010 Feb;2(1):71-86. doi: 10.2217/epi.09.44. Review. PubMed PMID: 22122748.
6: Daskalakis M, Blagitko-Dorfs N, Hackanson B. Decitabine. Recent Results Cancer Res. 2010;184:131-57. doi: 10.1007/978-3-642-01222-8_10. Review. PubMed PMID: 20072836.
7: Santos FP, Kantarjian H, Garcia-Manero G, Issa JP, Ravandi F. Decitabine in the treatment of myelodysplastic syndromes. Expert Rev Anticancer Ther. 2010 Jan;10(1):9-22. doi: 10.1586/era.09.164. Review. PubMed PMID: 20014881.
8: Stresemann C, Lyko F. Modes of action of the DNA methyltransferase inhibitors azacytidine and decitabine. Int J Cancer. 2008 Jul 1;123(1):8-13. doi: 10.1002/ijc.23607. Review. PubMed PMID: 18425818.
9: Jabbour E, Issa JP, Garcia-Manero G, Kantarjian H. Evolution of decitabine development: accomplishments, ongoing investigations, and future strategies. Cancer. 2008 Jun;112(11):2341-51. doi: 10.1002/cncr.23463. Review. PubMed PMID: 18398832.
10: Plimack ER, Kantarjian HM, Issa JP. Decitabine and its role in the treatment of hematopoietic malignancies. Leuk Lymphoma. 2007 Aug;48(8):1472-81. Review. PubMed PMID: 17701577.
Dacogen (decitabine) for Injection contains decitabine (5-aza-2'deoxycitidine), an analogue of the natural nucleoside 2'-deoxycytidine. Decitabine is a fine, white to almost white powder with the molecular formula of C8H12N4O4 and a molecular weight of 228.21. Its chemical name is 4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin2(1H)-one. Decitabine is slightly soluble in ethanol/water (50/50), methanol/water (50/50) and methanol; sparingly soluble in water and soluble in dimethylsulfoxide (DMSO). Dacogen (decitabine) for Injection is a white to almost white sterile lyophilized powder supplied in a clear colorless glass vial. Each 20 mL, single dose, glass vial contains 50 mg decitabine, 68 mg monobasic potassium phosphate (potassium dihydrogen phosphate) and 11.6 mg sodium hydroxide.
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.
Mechanism of Action
Decitabine is believed to exert its antineoplastic effects after phosphorylation and direct incorporation into DNA and inhibition of DNA methyltransferase, causing hypomethylation of DNA and cellular differentiation or apoptosis. Decitabine inhibits DNA methylation in vitro , which is achieved at concentrations that do not cause major suppression of DNA synthesis. Decitabine-induced hypomethylation in neoplastic cells may restore normal function to genes that are critical for the control of cellular differentiation and proliferation. In rapidly dividing cells, the cytotoxicity of decitabine may also be attributed to the formation of covalent adducts between DNA methyltransferase and decitabine incorporated into DNA. Non-proliferating cells are relatively insensitive to decitabine.
