Bicalutamide

Nonsteroidal antiandrogen used primarily in the treatment of prostate cancer. Bicalutamide competitively inhibits androgen binding to the androgen receptor, suppressing androgen-dependent signaling and growth of prostate cancer cells

CAS Number: 90357-06-5

Molecular Mass: 430.38 g/mol

Formula: C₁₈H₁₄F₄N₂O₄S

Smiles: N#CC1=CC=C(C=C1C(F)(F)F)NC(=O)C(O)(C)CS(=O)(=O)C2=CC=C(F)C=C2

Synonymes:

Bicalutamide, Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, (±)-, N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide, ICI 176334, Casodex, (±)-4′-Cyano-α,α,α-trifluoro-3-[(p-fluorophenyl)sulfonyl]-2-methyl-m-lactotoluidide, Cosudex, ZD 176334, Casode

Bioactivity: Androgen receptor antagonist; nonsteroidal antiandrogen; antineoplastic agent

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	278.15	-	1.545	[349]
1-Butanol	283.15	-	1.818	[349]
1-Butanol	288.15	-	2.143	[349]
1-Butanol	293.15	-	2.581	[349]
1-Butanol	298.15	-	3.047	[349]
1-Butanol	303.15	-	3.653	[349]
1-Butanol	308.15	-	4.319	[349]
1-Butanol	313.15	-	5.061	[349]
1-Butanol	318.15	-	5.851	[349]
1-Octanol	293.15	Form I	0.61^?	[6]
1-Octanol	298.15	Form I	0.7^?	[6]
1-Octanol	303.15	Form I	0.81^?	[6]
1-Octanol	308.15	Form I	0.91^?	[6]
1-Octanol	313.15	Form I	1.06^?	[6]
1-Propanol	278.15	-	1.744	[349]
1-Propanol	283.15	-	2.038	[349]
1-Propanol	288.15	-	2.406	[349]
1-Propanol	293.15	-	2.811	[349]
1-Propanol	298.15	-	3.295	[349]
1-Propanol	303.15	-	3.865	[349]
1-Propanol	308.15	-	4.441	[349]
1-Propanol	313.15	-	5.133	[349]
1-Propanol	318.15	-	5.942	[349]
Acetonitrile	278.15	-	22.99	[349]
Acetonitrile	283.15	-	26.93	[349]
Acetonitrile	288.15	-	31.17	[349]
Acetonitrile	293.15	-	35.73	[349]
Acetonitrile	298.15	-	40.37	[349]
Acetonitrile	303.15	-	45.61	[349]
Acetonitrile	308.15	-	51.99	[349]
Acetonitrile	313.15	-	58.59	[349]
Acetonitrile	318.15	-	66.37	[349]
Cyclohexane	288.15	-	0.0024	[349]
Cyclohexane	293.15	-	0.0035	[349]
Cyclohexane	298.15	-	0.0051	[349]
Cyclohexane	303.15	-	0.0071	[349]
Cyclohexane	308.15	-	0.0096	[349]
Cyclohexane	313.15	-	0.0128	[349]
Cyclohexane	318.15	-	0.0169	[349]
Ethanol	278.15	-	3.501	[349]
Ethanol	283.15	-	4.059	[349]
Ethanol	288.15	-	4.665	[349]
Ethanol	293.15	Form I	8.4^?	[6]
Ethanol	293.15	-	5.361	[349]
Ethanol	298.15	Form I	10.29^?	[6]
Ethanol	298.15	-	6.163	[349]
Ethanol	303.15	Form I	12.51^?	[6]
Ethanol	303.15	-	7.005	[349]
Ethanol	308.15	Form I	15.04^?	[6]
Ethanol	308.15	-	7.995	[349]
Ethanol	313.15	Form I	17.18^?	[6]
Ethanol	313.15	-	9.05	[349]
Ethanol	318.15	-	10.31	[349]
Ethyl acetate	278.15	-	6.443	[349]
Ethyl acetate	283.15	-	8.319	[349]
Ethyl acetate	288.15	-	10.77	[349]
Ethyl acetate	293.15	-	13.47	[349]
Ethyl acetate	298.15	-	16.81	[349]
Ethyl acetate	303.15	-	20.32	[349]
Ethyl acetate	308.15	-	23.81	[349]
Ethyl acetate	313.15	-	28.11	[349]
Ethyl acetate	318.15	-	32.67	[349]
Hexane	288.15	-	0.0013	[349]
Hexane	293.15	Form I	0.0024^?	[6]
Hexane	293.15	-	0.0019	[349]
Hexane	298.15	Form I	0.0035^?	[6]
Hexane	298.15	-	0.0027	[349]
Hexane	303.15	Form I	0.0049^?	[6]
Hexane	303.15	-	0.0038	[349]
Hexane	308.15	Form I	0.0066^?	[6]
Hexane	308.15	-	0.0051	[349]
Hexane	313.15	Form I	0.0089^?	[6]
Hexane	313.15	-	0.007	[349]
Hexane	318.15	Form I	0.0115^?	[6]
Hexane	318.15	-	0.0094	[349]
Isobutanol	278.15	-	1.081	[349]
Isobutanol	283.15	-	1.297	[349]
Isobutanol	288.15	-	1.546	[349]
Isobutanol	293.15	-	1.818	[349]
Isobutanol	298.15	-	2.131	[349]
Isobutanol	303.15	-	2.526	[349]
Isobutanol	308.15	-	2.985	[349]
Isobutanol	313.15	-	3.538	[349]
Isobutanol	318.15	-	4.168	[349]
Isopropanol	278.15	-	1.476	[349]
Isopropanol	283.15	-	1.803	[349]
Isopropanol	288.15	-	2.215	[349]
Isopropanol	293.15	-	2.646	[349]
Isopropanol	298.15	-	3.113	[349]
Isopropanol	303.15	-	3.637	[349]
Isopropanol	308.15	-	4.191	[349]
Isopropanol	313.15	-	4.761	[349]
Isopropanol	318.15	-	5.406	[349]
Methanol	278.15	-	8.971	[349]
Methanol	283.15	-	10.96	[349]
Methanol	288.15	-	13.04	[349]
Methanol	293.15	-	15.27	[349]
Methanol	298.15	-	17.76	[349]
Methanol	303.15	-	20.36	[349]
Methanol	308.15	-	23.2	[349]
Methanol	313.15	-	26.3	[349]
Methanol	318.15	-	29.75	[349]
Propyl acetate	278.15	-	15.13	[349]
Propyl acetate	283.15	-	17.53	[349]
Propyl acetate	288.15	-	20.11	[349]
Propyl acetate	293.15	-	22.83	[349]
Propyl acetate	298.15	-	25.9	[349]
Propyl acetate	303.15	-	29.51	[349]
Propyl acetate	308.15	-	33.86	[349]
Propyl acetate	313.15	-	38.82	[349]
Propyl acetate	318.15	-	44.58	[349]
Toluene	278.15	-	0.2027	[349]
Toluene	283.15	-	0.2439	[349]
Toluene	288.15	-	0.2988	[349]
Toluene	293.15	-	0.3618	[349]
Toluene	298.15	-	0.4375	[349]
Toluene	303.15	-	0.5156	[349]
Toluene	308.15	-	0.5969	[349]
Toluene	313.15	-	0.6859	[349]
Toluene	318.15	-	0.7779	[349]
Water	298.15	Form I	0.0027^?	[6]
Water	303.15	Form I	0.0035^?	[6]
Water	308.15	Form I	0.0045^?	[6]
Water	313.15	Form I	0.0056^?	[6]
Water	318.15	Form I	0.007^?	[6]

Thermodynamic parameters of solution

Solvent	Temperature [K]	Crystal form	ΔH_sol [kJ/mol]	ΔS_sol [J/mol/K]	ΔG_sol [kJ/mol]	Reference
1-Octanol	298.15	Form I	21.6	3.73	20.49	[6]
Ethanol	298.15	Form I	28.9	42.43	16.2	[6]
Hexane	303.15	Form I	49.2	50.7	34.2	[6]
Water	303.15	Form I	36.8	-7.37	39.0	[6]

Phase transitions

Transition type	Temperature [K]	Crystal form	ΔH [kJ/mol]	ΔS [J/mol/K]	ΔG [kJ/mol]	Reference
Melting	465.5	Form I	-	-	-	[6]
Sublimation	298.15	Form I	124.7	205.0	63.7	[11]

Molecule 3D descriptors

Descriptor	Value
PMI1	1329.3400
PMI2	9360.8756
PMI3	10075.8120
NPR1	0.1319
NPR2	0.9290
RadiusOfGyration	4.9117
InertialShapeFactor	0.0007
Eccentricity	0.9913
Asphericity	0.6563
SpherocityIndex	0.1580
PBF	0.8408