A DNA methyltransferase inhibitor
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Pro-drug Form(s)
133732',3',5'-triacetyl-5-Azacytidine
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5-Azacytidine

Item No. 11164

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-amino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
CAS Number
320-67-2
Synonyms
  • Antibiotic U 18496
  • 5-AzaC
  • Ladakamycin
  • Mylosar
  • NSC 102816
  • NSC 103-627
  • U 18496
  • WR 183027
Molecular Formula
C8H12N4O5
Formula Weight
244.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
O[C@]1([H])[C@@](O)([H])[C@](CO)([H])O[C@@]1([H])N2C=NC(N)=NC2=O
InChi Code
InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
InChi Key
NMUSYJAQQFHJEW-KVTDHHQDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 mg

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    Product Description

    5-Azacytidine, a chemical analogue of the DNA and RNA nucleoside cytidine, is an inhibitor of DNA methyltransferases, potentially serving to reverse epigenetic changes.1 It reduces hypermethylation associated with certain diseases, including myelodysplastic syndromes (IC50s = 2.4 and 2.6 μM for in vitro anti-myeloma activity) and cancer (IC50s ~ 0.4 μM for inhibiting proliferation of various cancer cell lines).2,3,4 5-Azacytidine has a reported half-life of 17 hours and is considerably cytotoxic; it must be incorporated into DNA to covalently trap DNA methyltransferases.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brueckner, B., Boy, R.G., Siedlecki, P., et al. Epigenetic reactivation of tumor suppressor genes by a novel small-molecule inhibitor of human DNA methyltransferases. Cancer Res. 65(14), 6305-6311 (2005).

    2. Esteller, M. Epigenetics in cancer. N. Engl. J. Med. 358(11), 1148-1159 (2008).

    3. Lyko, F., and Brown, R. DNA methyltransferase inhibitors and the development of epigenetic cancer therapies. J. Natl. Cancer Inst. 97(20), 1498-1506 (2005).

    4. Stresemann, C., Brueckner, B., Musch, T., et al. Functional diversity of DNA methyltransferase inhibitors in human cancer cell lines. Cancer Res. 66(5), 2794-2800 (2006).