Drug Information

Drug (ID: DG00860) and It's Reported Resistant Information
Name
Azacitidine
Synonyms
5-azacytidine; Azacitidine; 320-67-2; Ladakamycin; Azacytidine; Vidaza; Mylosar; 5-azacitidine; Azacitidinum; Azacitidina; Azacitidinum [INN-Latin]; 5-AZAC; Azacitidina [INN-Spanish]; NSC-102816; C8H12N4O5; NSC 102816; U-18496; 4-Amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one; UNII-M801H13NRU; NSC102816; 5AzaC; 4-Amino-1-beta-d-ribofuranosyl-1,3,5-triazin-2(1H)-one; Antibiotic U 18496; CHEBI:2038; M801H13NRU; 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one; 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; MFCD00006539; 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one; 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one; WR-183027; NCGC00090851-04; DSSTox_CID_116; U 18496; DSSTox_RID_75378; DSSTox_GSID_20116; U-18,496; CCRIS 60; SMR000857239; Vidaza (TN); HSDB 6879; 5-aza-CR; SR-01000075662; EINECS 206-280-2; BRN 0620461; Onureg; Azacitidine (JAN/USAN/INN); Azacitidine [USAN:INN:BAN]; 4-Amino-1-beta-D-ribofuranosyl-1,3,5-traizin-2(1H)-one; NS-17; 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2-one; CAS-320-67-2; Azacitidine (Vidaza); 2-(beta-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-one; Antibiotic U18496; U18496; Spectrum_001262; 4-Amino-1-beta-D-ribofuranosyl-1,3,5-triazine-2(1H)-one; Spectrum2_000786; Spectrum3_001509; Spectrum4_000922; Spectrum5_001166; MolMap_000062; A 2385; SCHEMBL3741; CHEMBL1489; Azacitidine (5-Azacytidine); Lopac0_000035; BSPBio_003157; KBioGR_001444; KBioGR_002556; KBioSS_001742; KBioSS_002565; MLS001333121; MLS001333122; MLS002153249; MLS002548894; DivK1c_000125; SPECTRUM1502111; SPBio_000892; GTPL6796; DTXSID9020116; BCBcMAP01_000083; HMS500G07; KBio1_000125; KBio2_001742; KBio2_002556; KBio2_004310; KBio2_005124; KBio2_006878; KBio2_007692; KBio3_002657; KBio3_003034; NMUSYJAQQFHJEW-KVTDHHQDSA-; pyrimidine antimetabolite: inhibits nucleic acid replication; cMAP_000082; NINDS_000125; HMS1921J22; HMS2092D08; HMS2231F15; HMS3259D19; HMS3260G11; Pharmakon1600-01502111; ZINC3861768; 5-Azacytidine, >=98% (HPLC); Tox21_111032; Tox21_302985; Tox21_500035; BDBM50424715; CCG-39046; NSC758186; s1782; Onureg (CC-486; oral azacitidine); AKOS015896938; Tox21_111032_1; AM83944; CS-1287; DB00928; LP00035; MCULE-8318770472; NC00672; NSC-758186; NSC103-627; 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triaz; IDI1_000125; NCGC00090851-01; NCGC00090851-02; NCGC00090851-03; NCGC00090851-05; NCGC00090851-06; NCGC00090851-07; NCGC00090851-08; NCGC00090851-10; NCGC00090851-14; NCGC00090851-22; NCGC00178234-01; NCGC00256541-01; NCGC00260720-01; AS-13697; HY-10586; SRI-10756_10; SRI-10756_12; WR183027; DB-006955; SL-000003; EU-0100035; D03021; F10504; J10124; 320A672; A821115; Q416451; J-700085; SR-01000075662-1; SR-01000075662-3; SR-01000075662-7; BRD-K03406345-001-02-1; BRD-K03406345-001-27-8; 4-Amino-1- -D-ribofuranosyl-1,3,5-triazin-2(1H)-one; Z1522566611; 4-Amino-1-(bet.-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; 4-Amino-1-beta-D-ribofuranosyl-1,3,5-tr iazin-2(1H)-one; s-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl- (8CI); Azacitidine, United States Pharmacopeia (USP) Reference Standard; 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; Ladakamycin; Azacitidine, Pharmaceutical Secondary Standard; Certified Reference Material; 1401238-97-8; 5-Azacytidine, Hybri-Max(TM), gamma-irradiated, lyophilized powder, BioXtra, suitable for hybridoma; 5AE; 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-1,3,5-triazin-3-ium-2-one
    Click to Show/Hide
Indication
In total 2 Indication(s)
Myelodysplastic syndrome [ICD-11: 2A37]
Approved
[1]
Myelodysplastic syndrome [ICD-11: 2A37]
Approved
[1]
Structure
Drug Resistance Disease(s)
Disease(s) with Resistance Information Discovered by Cell Line Test for This Drug (1 diseases)
Myelodysplastic syndrome [ICD-11: 2A37]
[1]
Target DNA [cytosine-5]-methyltransferase (DNMT) NOUNIPROTAC [1]
Click to Show/Hide the Molecular Information and External Link(s) of This Drug
Formula
C8H12N4O5
IsoSMILES
C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](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
PubChem CID
9444
ChEBI ID
CHEBI:2038
TTD Drug ID
D09FAZ
VARIDT ID
DR00983
INTEDE ID
DR0163
DrugBank ID
DB00928
Type(s) of Resistant Mechanism of This Drug due to Structure Alteration
  UAPP: Unusual Activation of Pro-survival Pathway
Drug Resistance Data Categorized by Their Corresponding Diseases
ICD-02: Benign/in-situ/malignant neoplasm
Click to Show/Hide the Resistance Disease of This Class
Brain cancer [ICD-11: 2A00]
Click to Show/Hide
Drug Sensitivity Data Categorized by Their Corresponding Mechanisms
  Unusual Activation of Pro-survival Pathway (UAPP) Click to Show/Hide
Key Molecule: Oxalosuccinate decarboxylase (IDH1) [2]
Sensitive Disease FGFR-tacc positive glioblastoma [ICD-11: 2A00.01]
 Disease Info 
Molecule Alteration Missense mutation
p.R132H (c.395G>A)
 Molecule Info 
Wild Type Structure Method: X-ray diffraction Resolution: 1.65  Å
PDB: 6BKX
Mutant Type Structure Method: X-ray diffraction Resolution: 1.88  Å
PDB: 4UMX
   Download The Information of Sequence       Download The Structure File   
RMSD: 3.46
TM score: 0.85834
Amino acid change:
R132H
 : Wild Type Structure
 : Mutant Type Structure
  Mutation site(s) have been marked in red
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M
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70
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100
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120
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L
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130
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140
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150
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160
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170
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H
H
N
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F
F
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E
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E
G
G
G
G
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A
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180
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190
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200
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330
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350
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370
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G
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410
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420
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H
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Click to Show/Hide the Structure
Experimental Note Identified from the Human Clinical Data
In Vitro Model Brain N.A.
In Vivo Model Female athymic nude mouse (NCI-Frederick) model Mus musculus
Experiment for
Molecule Alteration		 Western blot analysis
Experiment for
Drug Resistance		 Tumor volume measurement assay
References
Ref 1 Azacitidine resistance caused by LAMP2 deficiency: a therapeutic window for the use of autophagy inhibitors in MDS/AML patients .Autophagy. 2019 May;15(5):927-929. doi: 10.1080/15548627.2019.1586259. Epub 2019 Mar 1. 10.1080/15548627.2019.1586259
Ref 2 5-azacytidine reduces methylation, promotes differentiation and induces tumor regression in a patient-derived IDH1 mutant glioma xenograftOncotarget. 2013 Oct;4(10):1737-47. doi: 10.18632/oncotarget.1408.

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