AZACITIDINE

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Search structure


Trade Names	AZACITIDINE VIDAZA
Synonyms	5-azacitidine Azacitidine Ladakamycin NSC-102816 Onureg U-18,496 U-18496 Vidaza
Status
Molecule Category	Free-form
ATC	L01BC07
UNII	M801H13NRU
EPA CompTox	DTXSID9020116


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	NMUSYJAQQFHJEW-KVTDHHQDSA-N
Smiles	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

Bioactivity

Mechanism of Action	Action	Reference
DNA (cytosine-5)-methyltransferase 1 inhibitor	INHIBITOR	DailyMed Wikipedia Wikipedia


Protein: DNA (cytosine-5)-methyltransferase 1 Description: DNA (cytosine-5)-methyltransferase 1 Organism : Homo sapiens P26358 ENSG00000130816

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

Assay Description	Organism	Bioactivity	Reference
Compound was tested for its inhibitory activity against L1210 lymphoid leukemia	Mus musculus	409.0 nM
Antiproliferative activity against human A427 cells after 96 hrs by crystal violet assay	Homo sapiens	630.0 nM
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells at 20 uM after 1.5 mins by fluorescence assay	Homo sapiens	50.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	108.45 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	96.87 %
Inhibition of UHRF1 in human MCF7 cells assessed as reduction in global 5-methylcytosine level at 15 uM after 72 hrs by HPLC-MS/MS analysis relative to control	Homo sapiens	48.0 %
Antiproliferative activity against human SKM1-S cells after 48 hrs by XTT assay	Homo sapiens	500.0 nM
Antiproliferative activity against human SKM1-S cells after 48 hrs by DAPI-staining-based flow cytometric method	Homo sapiens	510.0 nM
Inhibition of human DNMT1 using polydeoxyinosine polydeoxycytosine DNA as substrate after 15 mins in presence of SAM by TR-FRET assay	Homo sapiens	300.0 nM
Growth inhibition of human KB cells	Homo sapiens	0.23 ug.mL-1
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-5.86 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	26.88 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	3.746 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.0 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.12 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.12 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.0 %

Cross References

Resources	Reference
ChEBI	2038
ChEMBL	CHEMBL1489
DrugBank	DB00928
DrugCentral	25
FDA SRS	M801H13NRU
Human Metabolome Database	HMDB0015063
Guide to Pharmacology	6796
KEGG	C11262
PDB	5AE
PharmGKB	PA451996
PubChem	9444
SureChEMBL	SCHEMBL3741
ZINC	ZINC000003861768

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).