General
Preferred name
AZACITIDINE
Synonyms
5-Azacytidine ()
5-AzaC ()
Mylosar ()
Ladakamycin ()
NSC 102816 ()
Vidaza ()
AZA ()
Azacitidine(Vidaza) ()
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one ()
Azacitidine (5-Azacytidine) ()
5-AzaC,Ladakamycin, AZA,5-Aza, CC-486,NSC 102816,5-Azacytidine ()
5-azacitidine ()
NSC-102816 ()
U-18,496 ()
Onureg ()
U-18496 ()
P&D ID
PD001379
CAS
320-67-2
1401238-97-8
Tags
prodrug
natural product
drug
available
Approved by
PMDA
EMA
FDA
First approval
2004
Drug Status
investigational
approved
Drug indication
Antineoplastic
Myelodysplastic syndrome
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION DNA methyltransferase and RNA inhibitor. Azacitidine inhibits DNA methylation in vitro , but not by directly interacting with the methyltransferase enzyme DNMT1. (GtoPdb)
ROE Following IV administration of radioactive azacitidine to 5 cancer patients, the cumulative urinary excretion was 85% of the radioactive dose.; Fecal excretion accounted for <1% of administered radioactivity over three days. Mean excretion of radioactivity in urine following SC administration of 14C-azacitidine was 50%.
MOA Azacitidine (5-azacytidine) is a chemical analogue of the cytosine nucleoside used in DNA and RNA. Azacitidine may induce antineoplastic activity by inhibition of DNA methyltransferase at low doses and cytotoxicity through incorporation into RNA and DNA at high doses. Covalent binding to DNA methyltransferase results in hypomethylation of DNA and prevents DNA synthesis. As azacitidine is a ribonucleoside, it incoporates into RNA to a larger extent than into DNA. The incorporation into RNA leads to the dissembly of polyribosomes, defective methylation and acceptor function of transfer RNA, and inhibition of the production of protein, resulting in cell death.
DESCRIPTION inhibitor of DNA methyltransferase (Informer Set)
DESCRIPTION DNA methyltransferase inhibitor (LOPAC library)
DESCRIPTION DNA methyltransferase inhibitor (Tocriscreen Plus)
DESCRIPTION ROCK inhibitor ; improves the efficiency of fibroblast reprogramming and induction of iPSCs (Tocris Bioactive Compound Library)
Cell lines
7
Organisms
1
Compound Sets
28
AdooQ Bioactive Compound Library
A10105
Cayman Chemical Bioactives
11164
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL1489
ChEMBL Drugs
CHEMBL1489
Drug Repurposing Hub
DrugBank
DB00928
DrugBank Approved Drugs
DB00928
DrugCentral
25
DrugCentral Approved Drugs
25
DrugMAP
DMTA5OE
DrugMAP Approved Drugs
DMTA5OE
Enamine BioReference Compounds
Guide to Pharmacology
6796
Informer Set
26874
JUMP-Target 1 Compound Set
9444
LINCS compound set
10300-101
LOPAC library
NCATS Inxight Approved Drugs
M801H13NRU
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
Azacitidine(Vidaza)
TargetMol Bioactive Compound Library
T1339
The Spectrum Collection
Tocris Bioactive Compound Library
3842
Tocriscreen Plus
3842
External IDs
42
Properties
(calculated by RDKit )
Molecular Weight
244.08
Hydrogen Bond Acceptors
9
Hydrogen Bond Donors
4
Rotatable Bonds
2
Ring Count
2
Aromatic Ring Count
1
cLogP
-3.17
TPSA
143.72
Fraction CSP3
0.62
Chiral centers
4.0
Largest ring
6.0
QED
0.43
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
DNMT1
RNA
DNA
DNA (cytosine-5)-methyltransferase 3A
DNA (cytosine-5)-methyltransferase 1
DNA methyltransferase (DNMT)
DNMT1, DNMT3A
DNMT3A
Autophagy,DNA Methyltransferase,Nucleoside Analog/Antimetabolite
Compound status
FDA
Target Type
Enzymes
Selectivity
DNA methyltransferase
MOA
DNA Methyltransferase inhibitor
Inhibitor
Antimetabolites
Apoptosis Inducers
DNA Methyltransferase (DNMT) Inhibitors
"DNMT1
DNA Methyltransferase (DNMT) Inhibitors"
Pathway
Chromatin/Epigenetic
Primary Target
DNA Methyltransferases
Member status
member
Indication
myelodysplastic diseases (MDS), anemia, chronic myelomonocytic leukemia (CMMoL)
Disease Area
hematologic malignancy, hematology
Therapeutic Class
Anticancer Agents
Source data