Sofosbuvir

Direct-acting antiviral drug used in combination therapy for chronic hepatitis C virus (HCV) infection. Sofosbuvir is converted intracellularly to an active uridine nucleotide analogue triphosphate that inhibits HCV NS5B RNA-dependent RNA polymerase and terminates viral RNA synthesis

CAS Number: 1190307-88-0

Molecular Mass: 529.45 g/mol

Formula: C₂₂H₂₉FN₃O₉P

Smiles: O=C(OC(C)C)C(NP(=O)(OC=1C=CC=CC1)OCC2OC(N3C=CC(=O)NC3=O)C(F)(C)C2O)C

Synonymes:

Sofosbuvir, L-Alanine, N-[[P(S),2′R]-2′-deoxy-2′-fluoro-2′-methyl-P-phenyl-5′-uridylyl]-, 1-methylethyl ester, PSI 7977, Sofosbuvir, GS 7977, Sovaldi, Hepcinat, Resof, Hepcvir, Sovihep, Isopropyl (2S)-2-[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyl-tetrahydrofuran-2-yl]methoxy-phenoxy-phosphoryl]amino]propionate, Sofos 400

Bioactivity: HCV NS5B RNA-dependent RNA polymerase inhibitor; antiviral agent

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	278.15	-	55.38	[339]
1-Butanol	283.15	-	68.76	[339]
1-Butanol	288.15	-	85.02	[339]
1-Butanol	293.15	-	107.4	[339]
1-Butanol	298.15	-	132.5	[339]
1-Butanol	303.15	-	163.8	[339]
1-Butanol	308.15	-	200.6	[339]
1-Butanol	313.15	-	244.2	[339]
1-Butanol	318.15	-	297.8	[339]
Acetone	278.15	-	208.4	[339]
Acetone	283.15	-	260.0	[339]
Acetone	288.15	-	329.9	[339]
Acetone	293.15	-	409.6	[339]
Acetone	298.15	-	505.8	[339]
Acetone	303.15	-	614.5	[339]
Acetone	308.15	-	740.9	[339]
Acetone	313.15	-	892.3	[339]
Acetone	318.15	-	1075.0	[339]
Acetonitrile	278.15	-	50.09	[339]
Acetonitrile	283.15	-	64.82	[339]
Acetonitrile	288.15	-	83.14	[339]
Acetonitrile	293.15	-	103.0	[339]
Acetonitrile	298.0	Form VIII	258.7^?	-
Acetonitrile	298.15	-	128.8	[339]
Acetonitrile	303.15	-	157.8	[339]
Acetonitrile	308.15	-	191.6	[339]
Acetonitrile	313.15	-	235.0	[339]
Acetonitrile	318.15	-	286.4	[339]
Cyclohexane	283.15	-	0.003	[339]
Cyclohexane	288.15	-	0.0046	[339]
Cyclohexane	293.15	-	0.0071	[339]
Cyclohexane	298.0	Form VIII	1.4 × 10⁻⁴	-
Cyclohexane	298.15	-	0.0102	[339]
Cyclohexane	303.15	-	0.0148	[339]
Cyclohexane	308.15	-	0.0208	[339]
Cyclohexane	313.15	-	0.0292	[339]
Cyclohexane	318.15	-	0.04111	[339]
Ethanol	278.15	-	207.9	[339]
Ethanol	283.15	-	257.9	[339]
Ethanol	288.15	-	322.8	[339]
Ethanol	293.15	-	394.2	[339]
Ethanol	298.15	-	480.2	[339]
Ethanol	303.15	-	572.2	[339]
Ethanol	308.15	-	684.3	[339]
Ethanol	313.15	-	816.3	[339]
Ethanol	318.15	-	977.2	[339]
Ethyl acetate	278.15	-	14.57	[339]
Ethyl acetate	283.15	-	19.96	[339]
Ethyl acetate	288.15	-	26.63	[339]
Ethyl acetate	293.15	-	34.9	[339]
Ethyl acetate	298.15	-	45.56	[339]
Ethyl acetate	303.15	-	58.07	[339]
Ethyl acetate	308.15	-	74.57	[339]
Ethyl acetate	313.15	-	95.29	[339]
Ethyl acetate	318.15	-	121.8	[339]
Toluene	278.15	-	0.0226	[339]
Toluene	283.15	-	0.0374	[339]
Toluene	288.15	-	0.0551	[339]
Toluene	293.15	-	0.08743	[339]
Toluene	298.15	-	0.1321	[339]
Toluene	303.15	-	0.1982	[339]
Toluene	308.15	-	0.3015	[339]
Toluene	313.15	-	0.4602	[339]
Toluene	318.15	-	0.6966	[339]
Water	278.15	-	0.348	[339]
Water	283.15	-	0.543	[339]
Water	288.15	-	0.7612	[339]
Water	293.15	-	1.071	[339]
Water	298.15	-	1.48	[339]
Water	303.15	-	2.054	[339]
Water	308.15	-	2.804	[339]
Water	313.15	-	3.812	[339]
Water	318.15	-	4.952	[339]

Thermodynamic parameters of solution

Solvent	Temperature [K]	Crystal form	ΔH_sol [kJ/mol]	ΔS_sol [J/mol/K]	ΔG_sol [kJ/mol]	Reference
Acetonitrile	298.0	Form VIII	-	-	1.77	-
Cyclohexane	298.0	Form VIII	-	-	37.5	-

Molecule 3D descriptors

Descriptor	Value
PMI1	2866.7041
PMI2	8803.0452
PMI3	9361.2238
NPR1	0.3062
NPR2	0.9404
RadiusOfGyration	4.4566
InertialShapeFactor	0.0003
Eccentricity	0.9520
Asphericity	0.3515
SpherocityIndex	0.3021
PBF	1.2821