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Compound Detail

CHEMBL1489

AZACITIDINE
💊 Approved Drug
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💊 Approved Drug
Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1489
Name AZACITIDINE
Phase Approved
Structure Type MOL
InChI Key NMUSYJAQQFHJEW-KVTDHHQDSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL3797973

Known Names

5-azacitidine Azacitidina Azacitidine Azacitidine accord Azacitidine betapharm Azacitidine celgene Azacitidine kabi Azacitidine mylan Ladakamycin NSC-102816 Onureg U-18,496 +2 more
10
Targets
36
Activities
2
Assay Types
6
PK Parameters
20
Publications
14
Known Names
20
Indications
4
Mechanisms

Molecular Properties

244.2
MW (Da)
-3.17
ALogP
9
HBA
4
HBD
143.7
PSA (Ų)
0.43
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2004
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product Prodrug
USAN Stem -tidine
USAN Year 1978

Extended Properties

Molecular Formula C8H12N4O5
MW 244.21
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 1.32

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA (cytosine-5)-methyltransferase 3A inhibitor INHIBITOR DNA (cytosine-5)-methyltransferase 3A ✓ ✓
DNA (cytosine-5)-methyltransferase 1 inhibitor INHIBITOR DNA (cytosine-5)-methyltransferase 1 ✓ ✓
DNA inhibitor INHIBITOR DNA ✓ ✓
RNA inhibitor INHIBITOR RNA ✓ ✓

Indications

Anemia, Refractory, with Excess of Blasts Leukemia, Myeloid, Acute Leukemia, Myelomonocytic, Chronic Myelodysplastic Syndromes Neoplasms Neoplasms Immunoblastic Lymphadenopathy Leukemia Leukemia, Myeloid Lymphoma Lymphoma, Large B-Cell, Diffuse Lymphoma, T-Cell, Peripheral Lymphoma, T-Cell, Peripheral Thrombocytopenia beta-Thalassemia beta-Thalassemia Breast Neoplasms Breast Neoplasms Breast Neoplasms, Male Carcinoma, Non-Small-Cell Lung

ATC Classification

L01BC07
azacitidine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 30 meas. best 6.52
EC50 6 meas. best 6.29

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DNA (cytosine-5)-methyltransferase 1
CHEMBL1993
 IC50 6.52 6.52 300.0 1
L1210
CHEMBL386
 IC50 6.39 6.39 409.0 1
Unchecked
CHEMBL612545
 IC50 6.3 4.9159 500.0 22
Unchecked
CHEMBL612545
 EC50 6.29 5.116 510.0 5
A-427
CHEMBL614515
 IC50 6.2 6.2 630.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.8 5.8 1590.0 1
5637
CHEMBL612565
 IC50 5.76 5.76 1730.0 1
HT-29
CHEMBL384
 IC50 5.42 5.42 3800.0 1
P388
CHEMBL389
 IC50 5.3 5.3 5000.0 1
MCF7
CHEMBL387
 IC50 5.17 5.17 6780.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 4.28 4.28 53000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 35.0 mL.min-1.kg-1 Homo sapiens
MRT 0.22 hr Homo sapiens
T1/2 0.36 hr Homo sapiens
T1/2 6.0 hr Rattus norvegicus
T1/2 48.0 hr -
T1/2 0.6833 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DNA (cytosine-5)-methyltransferase 1 IC50 = 300.0 nM 6.52 Inhibition of human DNMT1 using polydeoxyinosine polydeoxycytosine DNA as substr... 29953809
L1210 IC50 = 409.0 nM 6.39 Compound was tested for its inhibitory activity against L1210 lymphoid leukemia 3806615
Unchecked IC50 = 500.0 nM 6.3 Antiproliferative activity against human SKM1-S cells after 48 hrs by XTT assay 28094938
Unchecked EC50 = 510.0 nM 6.29 Antiproliferative activity against human SKM1-S cells after 48 hrs by DAPI-stain... 28094938
A-427 IC50 = 630.0 nM 6.2 Antiproliferative activity against human A427 cells after 96 hrs by crystal viol... 18434163
NON-PROTEIN TARGET IC50 = 1590.0 nM 5.8 Antiproliferative activity against human KYSE70 cells after 96 hrs by crystal vi... 18434163
5637 IC50 = 1730.0 nM 5.76 Antiproliferative activity against human 5637 cells after 96 hrs by crystal viol... 18434163
Unchecked IC50 = 1802.7 nM 5.74 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 2550.2 nM 5.59 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 3036.4 nM 5.52 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
HT-29 IC50 = 3800.0 nM 5.42 Antiproliferative activity against human HT-29 cells after 96 hrs by MTT assay 2778449
Unchecked IC50 = 4760.0 nM 5.32 PUBCHEM_BIOASSAY: Dose response counterscreen of uHTS chemical inhibitors of T-c... -
P388 IC50 = 5000.0 nM 5.3 Antiproliferative activity against mouse P388 cells after 48 hrs by MTT assay 2778449
MCF7 IC50 = 6780.0 nM 5.17 Antiproliferative activity against human MCF7 cells after 96 hrs by crystal viol... 18434163
Unchecked IC50 = 7400.4 nM 5.13 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked IC50 = 10060.0 nM 5.0 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Unchecked IC50 = 10800.0 nM 4.97 PUBCHEM_BIOASSAY: Dose response confirmation of uHTS chemical inhibitors of T-ce... -
Unchecked EC50 = 10820.0 nM 4.97 PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP... -
Unchecked IC50 = 11223.0 nM 4.95 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Unchecked IC50 = 11900.0 nM 4.92 PUBCHEM_BIOASSAY: Dose Response selectivity of uHTS chemical inhibitors of T-cel... -

Literature References

PubMed DOI Target Context # Activities
69026 10.1021/jm00216a013 L1210 28
27117260 10.1016/j.bmc.2016.03.052 Human immunodeficiency virus 1 12
74412 10.1021/jm00200a012 Mus musculus 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
69026 10.1021/jm00216a013 Mus musculus 8
28094938 10.1021/acs.jmedchem.6b01803 Unchecked 6
92567 10.1021/jm00196a015 Mus musculus 5
74412 10.1021/jm00200a012 L1210 5
2778449 10.1021/np50063a010 P388 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
69026 10.1021/jm00216a013 P388 4
18426954 10.1124/dmd.108.020479 ADMET 4
92567 10.1021/jm00196a015 L1210 4
2778449 10.1021/np50063a010 HT-29 4
33691794 10.1186/s13148-021-01037-1 A549 4
69026 10.1021/jm00216a013 No relevant target 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
69026 10.1021/jm00216a013 B16 3

Data from ChEMBL 36 via Core Engine