azacitidine   Click here for help

GtoPdb Ligand ID: 6796

Synonyms: 5-AZAC | 5-azacytidine | ladakamycin | Onureg® | Onureg® (CC-486; oral azacitidine) | U-18496 | Vidaza®
Approved drug PDB Ligand Immunopharmacology Ligand
azacitidine is an approved drug (FDA (2004), EMA (2009))
Compound class: Synthetic organic
Comment: DNA methyltransferase and RNA inhibitor. Azacitidine inhibits DNA methylation in vitro [3], but not by directly interacting with the methyltransferase enzyme DNMT1.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 143.72
Molecular weight 244.08
XLogP -1.81
No. Lipinski's rules broken 0
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Canonical SMILES OCC1OC(C(C1O)O)n1cnc(nc1=O)N
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc(nc1=O)N
InChI 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
1. Chen MY, Liao WS, Lu Z, Bornmann WG, Hennessey V, Washington MN, Rosner GL, Yu Y, Ahmed AA, Bast Jr RC. (2011)
Decitabine and suberoylanilide hydroxamic acid (SAHA) inhibit growth of ovarian cancer cell lines and xenografts while inducing expression of imprinted tumor suppressor genes, apoptosis, G2/M arrest, and autophagy.
Cancer, 117 (19): 4424-38. [PMID:21491416]
2. Dear AE. (2016)
Epigenetic Modulators and the New Immunotherapies.
N Engl J Med, 374 (7): 684-6. [PMID:26886527]
3. Jones PA, Taylor SM. (1980)
Cellular differentiation, cytidine analogs and DNA methylation.
Cell, 20 (1): 85-93. [PMID:6156004]
4. Stresemann C, Lyko F. (2008)
Modes of action of the DNA methyltransferase inhibitors azacytidine and decitabine.
Int J Cancer, 123 (1): 8-13. [PMID:18425818]