Azacytidine

An antineoplastic nucleoside analogue used primarily for the treatment of myelodysplastic syndromes and certain myeloid malignancies. It inhibits DNA methylation and can restore the expression of silenced genes.

CAS Number: 320-67-2

Molecular Mass: 244.21 g/mol

Formula: C₈H₁₂N₄O₅

Smiles: O=C1N=C(N=CN1C2OC(CO)C(O)C2O)N

Synonymes:

Azacytidine, 1,3,5-Triazin-2(1H)-one, 4-amino-1-β-D-ribofuranosyl-, s-Triazin-2(1H)-one, 4-amino-1-β-D-ribofuranosyl-, 4-Amino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one, Antibiotic U 18496, 5-Azacytidine, U 18496, NSC 102816, Azacitidine, Azacytidine, NSC 103-627, 5-AZCR, Mylosar, 5-AC, WR 183027, 5-AzaC, 5-AZC, Ladakamycin, Ledakamycin, Vidaza, CC 486, 5-Azacitidine, AZA, AZA (azacitidine), Azacitidine (AZA), MeSH ID: D001374, Onureg

Bioactivity: DNA methyltransferase inhibitor; antineoplastic agent

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Propanol	278.15	Form I	0.009702786^?	[2]
1-Propanol	283.15	Form I	0.014339949^?	[2]
1-Propanol	288.15	Form I	0.020299609^?	[2]
1-Propanol	293.15	Form I	0.02841237^?	[2]
1-Propanol	298.15	Form I	0.039524365^?	[2]
1-Propanol	303.15	Form I	0.052986265^?	[2]
1-Propanol	308.15	Form I	0.069925668^?	[2]
1-Propanol	313.15	Form I	0.088673464^?	[2]
1-Propanol	318.15	Form I	0.110765448^?	[2]
Acetonitrile	298.0	Form I	0.089^?	-
Cyclohexane	298.0	Form I	0.00028^?	-
Ethanol	278.15	Form I	0.02846272^?	[2]
Ethanol	283.15	Form I	0.040448931^?	[2]
Ethanol	288.15	Form I	0.055314594^?	[2]
Ethanol	293.15	Form I	0.075931452^?	[2]
Ethanol	298.15	Form I	0.099583529^?	[2]
Ethanol	303.15	Form I	0.1295	[2]
Ethanol	308.15	Form I	0.160930364^?	[2]
Ethanol	313.15	Form I	0.198357748^?	[2]
Ethanol	318.15	Form I	0.236127966^?	[2]
Isopropanol	278.15	Form I	0.0238537^?	[2]
Isopropanol	283.15	Form I	0.035102621^?	[2]
Isopropanol	288.15	Form I	0.051217007^?	[2]
Isopropanol	293.15	Form I	0.073942767^?	[2]
Isopropanol	298.15	Form I	0.10530436^?	[2]
Isopropanol	303.15	Form I	0.142551249^?	[2]
Isopropanol	308.15	Form I	0.191955838^?	[2]
Isopropanol	313.15	Form I	0.251213006^?	[2]
Isopropanol	318.15	Form I	0.317728001^?	[2]
Methanol	278.15	Form I	0.034786739^?	[2]
Methanol	283.15	Form I	0.049057126^?	[2]
Methanol	288.15	Form I	0.066440162^?	[2]
Methanol	293.15	Form I	0.090298976^?	[2]
Methanol	298.15	Form I	0.116172091^?	[2]
Methanol	303.15	Form I	0.144484493^?	[2]
Methanol	308.15	Form I	0.175066782^?	[2]
Methanol	313.15	Form I	0.211495575^?	[2]
Methanol	318.15	Form I	0.250947272^?	[2]
Water	278.15	Form I	7.646207202^?	[2]
Water	283.15	Form I	9.248900092^?	[2]
Water	288.15	Form I	10.92389817^?	[2]
Water	293.15	Form I	12.89754488^?	[2]
Water	298.15	Form I	14.92099486^?	[2]
Water	303.15	Form I	17.03587239^?	[2]
Water	308.15	Form I	19.27181507^?	[2]
Water	313.15	Form I	21.61943341^?	[2]
Water	318.15	Form I	24.41273648^?	[2]

Thermodynamic parameters of solution

Solvent	Temperature [K]	Crystal form	ΔH_sol [kJ/mol]	ΔS_sol [J/mol/K]	ΔG_sol [kJ/mol]	Reference
1-Propanol	298.15	Form I	45.74	58.94	28.2	[2]
Acetonitrile	298.0	Form I	-	-	19.6	-
Cyclohexane	298.0	Form I	-	-	33.9	-
Ethanol	298.15	Form I	39.95	45.13	26.52	[2]
Isopropanol	298.15	Form I	48.9	77.86	25.73	[2]
Methanol	298.15	Form I	36.98	33.23	27.09	[2]
Water	298.15	Form I	21.62	15.85	16.9	[2]

Molecule 3D descriptors

Descriptor	Value
PMI1	466.7502
PMI2	1896.9440
PMI3	2013.0984
NPR1	0.2319
NPR2	0.9423
RadiusOfGyration	2.9935
InertialShapeFactor	0.0020
Eccentricity	0.9727
Asphericity	0.4646
SpherocityIndex	0.2786
PBF	0.8471