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Drug Details

General Information of the Drug (ID: DR2370)
Name
Azacitidine
Synonyms
Azacitidina; Azacitidinum; Azacytidine; Ladakamycin; Mylosar; Vidaza; Mylo sar; Pharmion Brand of Azacitidine; A 2385; Antibiotic U 18496; U 18496; Wr 183027; Azacitidina [INN-Spanish]; Azacitidine [USAN:INN]; Azacitidinum [INN-Latin]; NS-17; Pyrimidine antimetabolite: inhibits nucleic acid replication; U-18496; Vidaz (TN); Vidaza (TN); WR-183027; Azacitidine (JAN/USAN/INN); S-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-(8CI); 2-(beta-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-one; 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; 4-Amino-1-beta-D-ribofuranosyl-1,3,5-traizin-2(1H)-one; 4-Amino-1-beta-D-ribofuranosyl-1,3,5-triazine-2(1H)-one; 4-Amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one; 4-Amino-1-beta-d-ribofuranosyl-1,3,5-triazin-2(1H)-one; 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triaz; 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one; 4-amino-1-beta-L-ribofuranosyl-1,3,5-triazin-2(1H)-one; 5 AZC; 5 Azacytidine; 5-AC; 5-AZAC; 5-AZCR; 5-aza-CR; 5-azacitidine; 5-azacytidine; 5-azacytidine, Mylosar, Ladakamycin, Vidaza, Azacitidine; 5AzaC
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Molecular Type
Small molecule
Disease Myelodysplastic syndrome [ICD-11: 2A37] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C8H12N4O5
PubChem CID
9444
Canonical SMILES
C1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N
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
InChIKey
NMUSYJAQQFHJEW-KVTDHHQDSA-N
CAS Number
CAS 320-67-2
ChEBI ID
CHEBI:2038
TTD Drug ID
D09FAZ
DrugBank ID
DB00928
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Arsenic trioxide      Realgar and orpiment     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression XAF1  Molecule Info 
Pathway MAP
                    In-vitro Model 8226 CVCL_0014 Plasma cell myeloma Homo sapiens
XG-7 CVCL_A772 Plasma cell myeloma Homo sapiens
                    Experimental
                    Result(s)
Combination of DNA methylation inhibitor 5-azacytidine and arsenic trioxide has synergistic activity in myeloma.
          Curcumin      Hellenia speciosa     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model HL-60 CVCL_0002 Adult acute myeloid leukemia Homo sapiens
U-937 CVCL_0007 Adult acute monocytic leukemia Homo sapiens
K-562 CVCL_0004 Chronic myelogenous leukemia Homo sapiens
OCI-AML-3 CVCL_1844 Adult acute myeloid leukemia Homo sapiens
                    Experimental
                    Result(s)
Combination of Azacitidine and curcumin showed a synergy in all leukemic lines and in most leukemic samples, with a decrease in proliferation and an increase in apoptosis compared to the activity of each drug separately. Azacitidine plus curcumin showed low cytotoxicity in healthy samples.
Target and Pathway
Target(s) DNA [cytosine-5]-methyltransferase (DNMT)  Molecule Info  [4]
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6796).
Reference 2 Combination of DNA methylation inhibitor 5-azacytidine and arsenic trioxide has synergistic activity in myeloma. Eur J Haematol. 2009 Mar;82(3):176-83.
Reference 3 Synergistic Antioncogenic Activity of Azacitidine and Curcumin in Myeloid Leukemia Cell Lines and Patient Samples. Anticancer Res. 2019 Sep;39(9):4757-4766.
Reference 4 The DNA methyltransferase inhibitors azacitidine, decitabine and zebularine exert differential effects on cancer gene expression in acute myeloid l... Leukemia. 2009 Jun;23(6):1019-28.
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Cite NPCDR
Visitor Map
Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China