e-Drug3D

1073

AZACITIDINE


INN
AZACITIDINE

(has an active metabolite)

cas 320-67-2
CLASS

ANTINEOPLASTIC
ANTIMETABOLITES
FAB MYELODYSPLASTIC SYNDROME
CYTOTOXIC
NUCLEOSIDE ANALOG OF CYTIDINE
HYPOMETHYLATION OF DNA AND RNA AFTER PHOSPHORYLATION BY KINASE UCK2

ROUTE (list)

INTRAVENOUS SUBCUTANEOUS ORAL

ATC code

L01BC07

PK parameters

F 89 PERCENT
VD 76 LITER
Cl 167 LITER / HOUR
t1/2 0.68 HOUR

Solubility

SPARINGLY SOLUBLE IN WATER


Target

TARGET URIDINE-CYTIDINE KINASE 2 (UCK2)

PDB
4QD3 (CRYSTAL STRUCTURE OF PEPTIDYL-TRNA HYDROLASE FROM PSEUDOMONAS AERUGINOSA WITH 5-AZACYTIDINE AT 1.89 ANGSTROM RESOLUTION)

Ligand code = 5AE (link to the list of PDB complexes)

Download experimental 3D coordinates of 5AE with added hydrogens

DrugCentral

DNA (cytosine-5)-methyltransferase 1 UNIPROT P26358 DNMT1

DNA (cytosine-5)-methyltransferase 3A UNIPROT Q9Y6K1 DNMT3A

Download SDF file 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one

Formula:
C8H12N4O5

Calculated chemical properties:

MW 244.22
NB_atoms 17
XLogP -3.17
PSA 137.65
NB_HD 5
NB_HA 9
fsp3 0.62
Lipinski(0=no;1=yes) 1

FDA
NDA 050794 (pdf not found) INN (AZACITIDINE) VIDAZA (BRISTOL-MYERS) APPROVAL= AP YEAR= 2004 NEWMOLECULARENTITY
NDA 201537 (pdf not found) INN (AZACITIDINE) AZACITIDINE (DR REDDYS) APPROVAL= AP YEAR= 2013
NDA 204949 (pdf not found) INN (AZACITIDINE) AZACITIDINE (NORVIUM BIOSCIENCE) APPROVAL= AP YEAR= 2016 DISCONTINUED
NDA 208216 (pdf not found) INN (AZACITIDINE) AZACITIDINE (ACTAVIS LLC) APPROVAL= AP YEAR= 2016
NDA 207518 (pdf not found) INN (AZACITIDINE) AZACITIDINE (SHILPA MEDICARE) APPROVAL= AP YEAR= 2016
NDA 207234 (pdf not found) INN (AZACITIDINE) AZACITIDINE (NATCO PHARMA LTD) APPROVAL= AP YEAR= 2017
NDA 209540 (pdf not found) INN (AZACITIDINE) AZACITIDINE (CIPLA) APPROVAL= AP YEAR= 2018
NDA 207475 (pdf not found) INN (AZACITIDINE) AZACITIDINE (ACCORD HLTHCARE) APPROVAL= AP YEAR= 2018
NDA 210748 (pdf not found) INN (AZACITIDINE) AZACITIDINE (LUPIN LTD) APPROVAL= AP YEAR= 2019 DISCONTINUED
NDA 209337 (pdf not found) INN (AZACITIDINE) AZACITIDINE (EUROHLTH INTL SARL) APPROVAL= AP YEAR= 2020
NDA 212128 (pdf not found) INN (AZACITIDINE) AZACITIDINE (MEITHEAL) APPROVAL= AP YEAR= 2020
NDA 214120 (pdf not found) INN (AZACITIDINE) ONUREG (BRISTOL) APPROVAL= AP YEAR= 2020
NDA 211549 (pdf not found) INN (AZACITIDINE) AZACITIDINE (AMNEAL) APPROVAL= AP YEAR= 2022
NDA 215066 (pdf not found) INN (AZACITIDINE) AZACITIDINE (EUGIA PHARMA) APPROVAL= AP YEAR= 2022
NDA 215905 (pdf not found) INN (AZACITIDINE) AZACITIDINE (JIANGSU HANSOH PHARM) APPROVAL= AP YEAR= 2023
NDA 212580 (pdf not found) INN (AZACITIDINE) AZACITIDINE (MSN LABS PVT LTD) APPROVAL= AP YEAR= 2024
NDA 215765 (pdf not found) INN (AZACITIDINE) AZACITIDINE (HETERO LABS LTD VI) APPROVAL= AP YEAR= 2024
NDA 217453 (pdf not found) INN (AZACITIDINE) AZACITIDINE (RELIANCE LIFE) APPROVAL= AP YEAR= 2025
NDA 218751 (pdf not found) INN (AZACITIDINE) AZACITIDINE (TEVA PHARMACEUTICALS DEVELOPMENT INC) APPROVAL= TA YEAR= 2025

Other links:

PubChem
ChemicalProbes

U.S. repository of Clinical Trials

VigiAccess
SIDER side effects

ChemSynthesis
Patent@SureChEMBL