AZACITIDINE

Search structure
Trade Names:
Synonyms:
Status: Approved (2004)
Entry Type: Small molecule
Molecule Category: UNKNOWN Prodrug
ATC: L01BC07
UNII: M801H13NRU

Structure
InChI Key NMUSYJAQQFHJEW-KVTDHHQDSA-N
Smile Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H12N4O5
Molecular Weight 244.21
AlogP -3.17
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 2.0
Polar Surface Area 143.72
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 17.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) -3.830 - EST
Henry's Law Constant 3.80E-21 atm-m3/mole EST
Atmospheric OH Rate Constant 9.72E-11 cm3/molecule-sec EST
Melting Point 229 deg C EXP
Water Solubility 8.90E+04 mg/L EST
Vapor Pressure 4.10E-12 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA (cytosine-5)-methyltransferase 1 inhibitor DailyMed Wikipedia Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Epigenetic regulator Reader Methyl-lysine/arginine binding protein Tudor domain
- - - - 48
Epigenetic regulator Reader Plant homeodomain
- - - - 48
Epigenetic regulator Writer DNA methyltransferase
- 300 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 109
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- - - - 50

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Thrombocytopenia 4 D013921 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Immunoblastic Lymphadenopathy 3 D007119 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Breast Neoplasms, Male 2 D018567 ClinicalTrials
Leukemia, Erythroblastic, Acute 2 D004915 ClinicalTrials
beta-Thalassemia 2 D017086 ClinicalTrials
beta-Thalassemia 2 D017086 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Rectal Neoplasms 2 D012004 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Colonic Neoplasms 2 D003110 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Primary Myelofibrosis 2 D055728 ClinicalTrials
Lymphoma, T-Cell, Peripheral 2 D016411 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Lymphoma, T-Cell, Peripheral 2 D016411 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Osteosarcoma 1 D012516 ClinicalTrials
Carcinoma, Squamous Cell 1 D002294 ClinicalTrials
Tuberculosis 1 D014376 ClinicalTrials
Carcinoma, Pancreatic Ductal 1 D021441 ClinicalTrials
Carcinoma, Renal Cell 1 D002292 ClinicalTrials
Lymphoma, Non-Hodgkin 1 D008228 ClinicalTrials
Head and Neck Neoplasms 1 D006258 ClinicalTrials
Ependymoma 1 D004806 ClinicalTrials
Ependymoma 1 D004806 ClinicalTrials
Hodgkin Disease 1 D006689 ClinicalTrials
Colorectal Neoplasms 1 D015179 ClinicalTrials
Esophageal Neoplasms 1 D004938 ClinicalTrials
Ovarian Neoplasms 1 D010051 ClinicalTrials
Myelodysplastic-Myeloproliferative Diseases 1 D054437 ClinicalTrials
Liposarcoma 1 D008080 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 1 D015464 ClinicalTrials
Brain Neoplasms 0 D001932 ClinicalTrials

Related Entries

MCS

Scaffolds

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Blood and lymphatic system disorders
12.54
General disorders and administration site conditions
11.92
Infections and infestations
11.21
Investigations
9.39
Gastrointestinal disorders
8.68
Respiratory, thoracic and mediastinal disorders
8.48
Vascular disorders
6.76
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
4.2
Injury, poisoning and procedural complications
3.99
Cardiac disorders
3.76
Skin and subcutaneous tissue disorders
3.47
Metabolism and nutrition disorders
3.34
Nervous system disorders
2.97
Renal and urinary disorders
2.18

Cross References

Resources Reference
CAS NUMBER 320-67-2
ChEBI 2038
ChEMBL CHEMBL1489
DrugBank DB00928
DrugCentral 25
EPA CompTox DTXSID9020116
FDA SRS M801H13NRU
Human Metabolome Database HMDB0015063
Guide to Pharmacology 6796
KEGG C11262
PDB 5AE
PharmGKB PA451996
PubChem 9444
SureChEMBL SCHEMBL3741
ZINC ZINC000003861768
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