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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1489
CHEMBL1489
Compound Name AZACITIDINE
ChEMBL Synonyms AZACITIDINE | LADAKAMYCIN | U-18,496 | VIDAZA
Max Phase 4 (Approved)
Trade Names VIDAZA | AZACITIDINE
Molecular Formula C8H12N4O5

Additional synonyms for CHEMBL1489 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NC1=NC(=O)N(C=N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
Standard InChI InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13 ...
Download InChI
Standard InChI Key NMUSYJAQQFHJEW-KVTDHHQDSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1489

Molecule Features

CHEMBL1489 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:Y Oral:N Parenteral:Y Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA DailyMed
DNA (cytosine-5)-methyltransferase 1 inhibitor DNA (cytosine-5)-methyltransferase 1 DailyMed
DNA (cytosine-5)-methyltransferase 3A inhibitor DNA (cytosine-5)-methyltransferase 3A DailyMed
RNA inhibitor RNA DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma1ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome4ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma1ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma2ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma2ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma1ClinicalTrials
Hematologic NeoplasmsD019337EFO:0001642lymphoid neoplasm1ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
Leukemia, Erythroblastic, AcuteD004915EFO:1001257acute erythroblastic leukemia2ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia3ClinicalTrials
Leukemia, Myelomonocytic, ChronicD015477EFO:1001779chronic myelomonocytic leukemia4ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
LymphomaD008223EFO:0000574lymphoma1ClinicalTrials
EpendymomaD004806EFO:1000028ependymoma1ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
beta-ThalassemiaD017086Orphanet:848Beta-thalassemia2ClinicalTrials
Anemia, Refractory, with Excess of BlastsD000754EFO:0003811refractory anemia with excess blasts4DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma1ClinicalTrials
LiposarcomaD008080EFO:0000569liposarcoma1ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma1ClinicalTrials
beta-ThalassemiaD017086Orphanet:231214Beta-thalassemia major2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma1ClinicalTrials
MelanomaD008545EFO:0000389cutaneous melanoma2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
Brain NeoplasmsD001932EFO:0003833brain neoplasm0ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia1ClinicalTrials
ThrombocytopeniaD013921HP:0001873thrombocytopenia3ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma1ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma1ClinicalTrials
MelanomaD008545EFO:0002617metastatic melanoma2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
Primary MyelofibrosisD055728EFO:0002430primary myelofibrosis2ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia1ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells2ClinicalTrials

Clinical Data

ClinicalTrials.gov AZACITIDINE
The Cochrane Collaboration AZACITIDINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1489. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 1.000
CHEMBL3360 Adenosine A3 receptor Rattus norvegicus 1.000
CHEMBL226 Adenosine A1 receptor Homo sapiens 1.000
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 1.000
CHEMBL1997 Equilibrative nucleoside transporter 1 Homo sapiens 1.000
CHEMBL256 Adenosine A3 receptor Homo sapiens 1.000
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 1.000
CHEMBL5662 2,3-dihydroxybenzoate-AMP ligase Mycobacterium tuberculosis 1.000
CHEMBL3589 Adenosine kinase Homo sapiens 1.000
CHEMBL251 Adenosine A2a receptor Homo sapiens 1.000
CHEMBL1293237 Bloom syndrome protein Homo sapiens 1.000
CHEMBL1795117 Histone-lysine N-methyltransferase, H3 lysine-79 specific Homo sapiens 1.000
CHEMBL4398 Purinergic receptor P2Y2 Homo sapiens 1.000
CHEMBL5720 P2Y purinoceptor 1 Meleagris gallopavo 1.000
CHEMBL2664 Adenosylhomocysteinase Homo sapiens 1.000
CHEMBL4837 Adhesin protein fimH Escherichia coli K-12 1.000
CHEMBL4714 Pyrimidinergic receptor P2Y6 Homo sapiens 1.000
CHEMBL2966 Adenosine deaminase Bos taurus 1.000
CHEMBL3884 Sodium/glucose cotransporter 2 Homo sapiens 1.000
CHEMBL1910 Adenosine deaminase Homo sapiens 0.999



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 1.000
CHEMBL3360 Adenosine A3 receptor Rattus norvegicus 1.000
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 1.000
CHEMBL226 Adenosine A1 receptor Homo sapiens 1.000
CHEMBL2982 Adenosine kinase Toxoplasma gondii 1.000
CHEMBL1997 Equilibrative nucleoside transporter 1 Homo sapiens 1.000
CHEMBL256 Adenosine A3 receptor Homo sapiens 1.000
CHEMBL251 Adenosine A2a receptor Homo sapiens 1.000
CHEMBL5662 2,3-dihydroxybenzoate-AMP ligase Mycobacterium tuberculosis 1.000
CHEMBL2664 Adenosylhomocysteinase Homo sapiens 1.000
CHEMBL2966 Adenosine deaminase Bos taurus 1.000
CHEMBL3589 Adenosine kinase Homo sapiens 1.000
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 1.000
CHEMBL4696 Glycogen phosphorylase, muscle form Oryctolagus cuniculus 1.000
CHEMBL4398 Purinergic receptor P2Y2 Homo sapiens 1.000
CHEMBL1795117 Histone-lysine N-methyltransferase, H3 lysine-79 specific Homo sapiens 1.000
CHEMBL5720 P2Y purinoceptor 1 Meleagris gallopavo 1.000
CHEMBL4714 Pyrimidinergic receptor P2Y6 Homo sapiens 1.000
CHEMBL2284 Glyceraldehyde-3-phosphate dehydrogenase liver Homo sapiens 1.000
CHEMBL2123 Pyrimidinergic receptor P2Y4 Homo sapiens 1.000

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
244.2 244.0808 -3.17 2 143.72 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
9 4 0 9 5 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.46 3.29 -2.19 -2.19 1 17 0.43

Structural Alerts

There are no structural alerts for CHEMBL1489

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BC - Pyrimidine analogues
L01BC07 - azacitidine

ChemSpider ChemSpider:NMUSYJAQQFHJEW-KVTDHHQDSA-N
DailyMed azacitidine
PubChem SID: 124890084 SID: 144204583 SID: 144213302 SID: 170465076 SID: 17390033 SID: 26752817 SID: 50105470 SID: 50105471 SID: 50122846 SID: 56320704 SID: 56323580 SID: 90341307
Wikipedia Azacitidine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1489



ACToR 320-67-2
BindingDB 50424715
ChEBI 2038
DrugBank DB00928
DrugCentral 25
eMolecules 478923
EPA CompTox Dashboard DTXSID9020116
FDA SRS M801H13NRU
Guide to Pharmacology 6796
Human Metabolome Database HMDB0015063
IBM Patent System 24507197B5C7C4BBA2643A9F584C9CB3
KEGG Ligand C11262
LINCS LSM-5218
Mcule MCULE-8318770472
MolPort MolPort-003-665-502
NIH Clinical Collection SAM002264595
Nikkaji J1.523G
NMRShiftDB 20209750
PDBe 5AE
PharmGKB PA451996
PubChem 9444
PubChem: Drugs of the Future 12013374
PubChem: Thomson Pharma 14749656 15019893
Selleck Azacitidine(Vidaza)
SureChEMBL SCHEMBL3741
ZINC ZINC000003861768

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/NMUSYJAQQFHJEW-KVTDHHQDSA-N spacer
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