5AE

4-amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one

Created: 2014-05-19
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count29
Chiral Atom Count4
Bond Count30
Aromatic Bond Count0
2D diagram of 5AE

Chemical Component Summary

Name4-amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
Synonyms5-azacytidine
Systematic Name (OpenEye OEToolkits)4-azanyl-1-[(2R,3R,4S,5R)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]-1,3,5-triazin-2-one
FormulaC8 H12 N4 O5
Molecular Weight244.205
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C1N=C(N=CN1C2OC(C(O)C2O)CO)N
SMILESCACTVS3.385NC1=NC(=O)N(C=N1)[CH]2O[CH](CO)[CH](O)[CH]2O
SMILESOpenEye OEToolkits1.7.6C1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N
Canonical SMILESCACTVS3.385 NC1=NC(=O)N(C=N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
Canonical SMILESOpenEye OEToolkits1.7.6 C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N
InChIInChI1.03 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
InChIKeyInChI1.03 NMUSYJAQQFHJEW-KVTDHHQDSA-N

Drug Info: DrugBank

DrugBank IDDB00928 
NameAzacitidine
Groups
  • approved
  • investigational
DescriptionAzacitidine is a pyrimidine nucleoside analogue with anti-neoplastic activity. It differs from cytosine by the presence of nitrogen in the C5-position, key in its hypomethylating activity.[A1406,A1413,A1415] Two main mechanisms of action have been proposed for azacitidine. One of them is the induction of cytotoxicity. As an analogue of cytidine, it is able to incorporate into RNA and DNA, disrupting RNA metabolism and inhibiting protein and DNA synthesis. The other one is through the inhibition of DNA methyltransferase, impairing DNA methylation.[A1407] Due to its anti-neoplastic activity and its ability to inhibit methylation in replicating DNA, azacytidine has been used mainly used in the treatment of myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML), two types of cancer characterized by the presence of aberrant DNA methylation.[A1407,A1410,A1411,A1416,A1417] In May 2004, the FDA approved the use of azacitidine administered subcutaneously for the treatment of MDS of all French-American-British (FAB) subtypes. In January 2007, the FDA approved the intravenous administration of azacitidine.[A1415] The use of oral azacitidine for the treatment of AML in patients in complete remission was approved by the FDA in September 2020.[L35335]
Synonyms
  • Azacitidina
  • Azacytidine
  • 4-amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one
  • 5-azacytidine
  • Azacitidinum
Brand Names
  • Azacitidine
  • Azacitidine For
  • Nat-azacitidine
  • Azacitidine Mylan
  • Onureg
IndicationAzacitidine (for subcutaneous or intravenous use) is indicated for the treatment of adult patients with the following French-American-British (FAB) myelodysplastic syndrome (MDS) subtypes: refractory anemia (RA) or refractory anemia with ringed sideroblasts (RARS) (if accompanied by neutropenia or thrombocytopenia or requiring transfusions), refractory anemia with excess blasts (RAEB), refractory anemia with excess blasts in transformation (RAEB-T), and chronic myelomonocytic leukemia (CMMoL). Azacitidine is also indicated for the treatment of pediatric patients aged 1 month and older with newly diagnosed Juvenile Myelomonocytic Leukemia (JMML).[L41910,L46861] Azacitidine (for oral use) is indicated for continued treatment of adult patients with acute myeloid leukemia (AML) who achieved first complete remission or complete remission with incomplete blood count recovery following intensive induction chemotherapy and are not able to complete intensive curative therapy.[L35335]
Categories
  • Antimetabolites
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Aza Compounds
  • Cytidine Deaminase Substrates
ATC-CodeL01BC07
CAS number320-67-2

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA (cytosine-5)-methyltransferase 1MPARTAPARVPTLAVPAISLPDDVRRRLKDLERDSLTEKECVKEKLNLLH...unknowninhibitor
RNA-unknownother
DNA-unknownother
Cytidine deaminaseMAQKRPACTLKPECVQQLLVCSQEAKKSAYCPYSHFPVGAALLTQEGRIF...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1489
PubChem 9444
ChEMBL CHEMBL1489
ChEBI CHEBI:2038