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/h4-6,13-14H,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
Technical Data
Appearance: white solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Certificate of Analysis: View current batch of CoA
QC Data: View NMR, View HPLC, View MS
Safety Data Sheet (MSDS): View Material Safety Data Sheet (MSDS)
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 to 50 mM in water and to 50 mM in DMSO
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).
Harmonized System Code: 293490
Additional Information
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.
References
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