Flutamide

An orally administered nonsteroidal antiandrogen used primarily in combination with androgen deprivation therapy for the treatment of prostate cancer. Flutamide is extensively metabolized to its active metabolite, 2-hydroxyflutamide, which competitively inhibits androgen binding to androgen receptors, suppressing androgen-dependent gene transcription and tumor growth. Unlike steroidal antiandrogens, flutamide has no significant intrinsic androgenic activity. Its clinical use has declined in favor of newer antiandrogens because of adverse effects, particularly potentially severe hepatotoxicity, as well as gynecomastia and gastrointestinal disturbances

CAS Number: 13311-84-7

Molecular Mass: 276.21 g/mol

Formula: C₁₁H₁₁F₃N₂O₃

Smiles: CC(C)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1

Synonymes:

Flutamide, flutamide, 13311-84-7, Eulexin, Niftolide, Drogenil, Sch 13521, 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide, niftolid, NFBA, Flutamida, Flutamidum, Sch-13521, Eulexine, 4'-Nitro-3'-trifluoromethylisobutyranilide, 2-Methyl-N-(4-nitro-3-[trifluoromethyl]phenyl)propanamide, Propanamide, 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-, SCH13521, DTXSID7032004, alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide, NSC-215876, Propanamide, 2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)-, 76W6J0943E, CHEBI:5132, DTXCID9011121, Flutacell, ApoFlutamide, NovoFlutamide, Apo Flutamide, Fluta cell, Novo Flutamide, FlutaGRY, PMS Flutamide, Fluta GRY, 2-Methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide, RefChem:55220, L02BB01, 236-341-9, Euflex, Niftholide, Flutamin, Cebatrol, veterinary, N-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)ISOBUTYRAMIDE, MFCD00072009, NSC 215876, CHEMBL806, 4-Nitro-3-(trifluoromethyl)isobutyranilide, 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propionamide, NCGC00015452-09, Chimax, Odyne, 4'-Nitro-3'-trifluoromethylisobutyramilide, CAS-13311-84-7, Ham's F-12 medium, Flutamidum [INN-Latin], Flutamida [INN-Spanish], Flutamide USP25, N-[4-Nitro-3-(trifluoromethyl)phenyl]isobutyramide, Prostandril, .alpha.,.alpha.,.alpha.-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide, SMR000058187, Eulexin (TN), CCRIS 7246, m-Propionotoluidide,.alpha.,.alpha.-trifluoro-, SR-01000075888, EINECS 236-341-9, NK-601, BRN 2157663, .alpha.,.alpha.-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide, m-Propionotoluidide,.alpha.,.alpha.-trifluoro-2-methyl-4'-nitro-, Flutamide CRS, UNII-76W6J0943E, 4'-Nitro-3'-(trifluoromethyl)isobutyranilide, Flutamide [USAN:USP:INN:BAN], Prestwick_228, Flutamide (Eulexin), Flutamide (Standard), Spectrum_001210, CPD000058187, FLUTAMIDE [INN], FLUTAMIDE [JAN], FLUTAMIDE [MI], FLUTAMIDE [USAN], Prestwick0_000180, Prestwick1_000180, Prestwick2_000180, Prestwick3_000180, Spectrum2_001201, Spectrum3_001421, Spectrum4_000829, Spectrum5_001450, Lopac-F-9397, F0663, Flutamide (pubertal study), FLUTAMIDE [MART.], F 9397, FLUTAMIDE [USP-RS], FLUTAMIDE [WHO-DD], SCHEMBL3934, Lopac0_000557, BSPBio_000079, BSPBio_003122, KBioGR_001377, KBioSS_001690, MLS000069634, MLS001065596, MLS002548892, DivK1c_000459, SPECTRUM1500995, Flutamide - Bio-X trade mark, SPBio_000982, SPBio_002000, Flutamide (JP18/USP/INN), BPBio1_000087, GTPL6943, orb1310563, FLUTAMIDE [EP IMPURITY], FLUTAMIDE [ORANGE BOOK], CHEMBL4759307, FLUTAMIDE [EP MONOGRAPH], SCHEMBL12932289, SCHEMBL29349783, HMS501G21, HY-B0022R, KBio1_000459, KBio2_001690, KBio2_004258, KBio2_006826, KBio3_002342, FLUTAMIDE [USP MONOGRAPH], NINDS_000459, GLXC-07722, HMS1568D21, HMS1921O16, HMS2090I18, HMS2092O14, HMS2095D21, HMS2230P19, HMS3259I03, HMS3261P15, HMS3373C12, HMS3655G22, HMS3712D21, HMS5080H03, Pharmakon1600-01500995, HY-B0022, MSK11432, YIA13472, Tox21_110154, Tox21_202169, Tox21_300536, Tox21_500557, BDBM50131270, CCG-39105, EBC-03834, m-Propionotoluidide, 2-methyl-4'-nitro-alpha,alpha,alpha-triflouro-, m-Propionotoluidide, alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro-, NSC147834, NSC215876, NSC757817, s1908, SBB006930, AKOS001025465, AKOS015994751, AKOS025243203, m-Propionotoluidide, .alpha.,.alpha.,.alpha.-trifluoro-2-methyl-4'-nitro-, Tox21_110154_1, AB02835, DB00499, FF23510, KS-5091, LP00557, NC00451, NSC-147834, NSC-757817, SDCCGSBI-0050540.P004, IDI1_000459, NCGC00015452-01, NCGC00015452-02, NCGC00015452-03, NCGC00015452-04, NCGC00015452-05, NCGC00015452-06, NCGC00015452-07, NCGC00015452-08, NCGC00015452-10, NCGC00015452-11, NCGC00015452-12, NCGC00015452-13, NCGC00015452-14, NCGC00015452-15, NCGC00015452-16, NCGC00015452-19, NCGC00015452-20, NCGC00015452-32, NCGC00091460-01, NCGC00091460-02, NCGC00091460-03, NCGC00091460-04, NCGC00091460-05, NCGC00091460-06, NCGC00091460-07, NCGC00091460-08, NCGC00091460-09, NCGC00254495-01, NCGC00259718-01, NCGC00261242-01, AC-24192, BF166239, ST058409, SY036411, SBI-0050540.P003, DB-042163, 3'-Trifluoromethyl-4'-Nitro-Isobutyranilide, AB00052188, EU-0100557, NS00002675, SW196536-4, T0489, 4''-nitro-3''-trifluoromethylisobutyranilide, A10796, C07653, D00586, EN300-119548, AB00052188-09, AB00052188_10, AB00052188_11, F358096, Q418669, SR-01000075888-1, SR-01000075888-6, SR-01000075888-7, SR-01000075888-9, BRD-K28307902-001-05-0, BRD-K28307902-001-20-9, BRD-K28307902-001-21-7, Flutamide, certified reference material, TraceCERT(R), Z56755651, Flutamide, European Pharmacopoeia (EP) Reference Standard, N1-[4-nitro-3-(trifluoromethyl)phenyl]-2-methylpropanamide, 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide #, Flutamide, United States Pharmacopeia (USP) Reference Standard, alpha,alpha,alpha-trifluoro-2-methyl-4''-nitro-m-propionotoluidide, m-Propionotoluidide, 2-methyl-4'-nitro-.alpha.,.alpha.,.alpha.-trifluoro-, Flutamide for system suitability, European Pharmacopoeia (EP) Reference Standard, 37209-54-4

Bioactivity: Nonsteroidal androgen receptor (AR) antagonist; first-generation antiandrogen; antineoplastic agent

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1,4-Dioxane	283.15	-	448.0	[146]
1,4-Dioxane	283.15	-	397.0	[147]
1,4-Dioxane	288.15	-	527.3	[146]
1,4-Dioxane	288.15	-	476.4	[147]
1,4-Dioxane	293.15	-	619.5	[146]
1,4-Dioxane	293.15	-	578.5	[147]
1,4-Dioxane	298.15	-	729.1	[146]
1,4-Dioxane	298.15	-	692.6	[147]
1,4-Dioxane	303.15	-	853.1	[146]
1,4-Dioxane	303.15	-	816.2	[147]
1,4-Dioxane	308.15	-	999.6	[146]
1,4-Dioxane	308.15	-	957.0	[147]
1,4-Dioxane	313.15	-	1184.0	[146]
1,4-Dioxane	313.15	-	1125.5	[147]
1,4-Dioxane	318.15	-	1399.6	[146]
1,4-Dioxane	318.15	-	1345.8	[147]
1,4-Dioxane	323.15	-	1600.5	[146]
1,4-Dioxane	323.15	-	1671.0	[147]
1-Butanol	278.15	-	157.8	[147]
1-Butanol	283.15	-	176.9	[147]
1-Butanol	288.15	-	201.1	[147]
1-Butanol	293.15	-	230.3	[147]
1-Butanol	298.15	-	260.0	[147]
1-Butanol	303.15	-	297.2	[147]
1-Butanol	308.15	-	341.6	[147]
1-Butanol	313.15	-	393.2	[147]
1-Butanol	318.15	-	461.4	[147]
1-Butanol	323.15	-	541.1	[147]
1-Propanol	278.15	-	193.3	[147]
1-Propanol	283.15	-	216.1	[147]
1-Propanol	288.15	-	246.9	[147]
1-Propanol	293.15	-	276.9	[147]
1-Propanol	298.15	-	312.8	[147]
1-Propanol	303.15	-	356.9	[147]
1-Propanol	308.15	-	408.3	[147]
1-Propanol	313.15	-	470.9	[147]
1-Propanol	318.15	-	547.3	[147]
1-Propanol	323.15	-	634.0	[147]
2-Methoxyethanol	278.15	-	490.6	[148]
2-Methoxyethanol	283.15	-	529.5	[148]
2-Methoxyethanol	288.15	-	582.6	[148]
2-Methoxyethanol	293.15	-	634.1	[148]
2-Methoxyethanol	298.15	-	695.6	[148]
2-Methoxyethanol	303.15	-	759.9	[148]
2-Methoxyethanol	308.15	-	835.4	[148]
2-Methoxyethanol	313.15	-	922.4	[148]
2-Methoxyethanol	318.15	-	1019.7	[148]
2-Methoxyethanol	323.15	-	1133.0	[148]
Acetone	278.15	-	875.7	[147]
Acetone	278.15	-	743.9	[148]
Acetone	283.15	-	959.5	[147]
Acetone	283.15	-	800.1	[148]
Acetone	288.15	-	1119.7	[147]
Acetone	288.15	-	858.0	[148]
Acetone	293.15	-	1306.6	[147]
Acetone	293.15	-	917.7	[148]
Acetone	298.15	-	1533.6	[147]
Acetone	298.15	-	986.2	[148]
Acetone	303.15	-	1799.5	[147]
Acetone	303.15	-	1063.9	[148]
Acetone	308.15	-	2120.2	[147]
Acetone	308.15	-	1148.2	[148]
Acetone	313.15	-	2502.5	[147]
Acetone	313.15	-	1250.0	[148]
Acetone	318.15	-	2956.6	[147]
Acetone	318.15	-	1359.0	[148]
Acetone	323.15	-	3460.2	[147]
Acetone	323.15	-	1488.5	[148]
Acetonitrile	278.15	-	338.0	[146]
Acetonitrile	278.15	-	322.2	[147]
Acetonitrile	283.15	-	432.2	[146]
Acetonitrile	283.15	-	408.3	[147]
Acetonitrile	288.15	-	549.0	[146]
Acetonitrile	288.15	-	525.3	[147]
Acetonitrile	293.15	-	683.3	[146]
Acetonitrile	293.15	-	712.4	[147]
Acetonitrile	298.15	-	880.6	[146]
Acetonitrile	298.15	-	975.3	[147]
Acetonitrile	303.15	-	1119.2	[146]
Acetonitrile	303.15	-	1276.5	[147]
Acetonitrile	308.15	-	1424.7	[146]
Acetonitrile	308.15	-	1677.4	[147]
Acetonitrile	313.15	-	1811.7	[146]
Acetonitrile	313.15	-	2155.2	[147]
Acetonitrile	318.15	-	2327.6	[146]
Acetonitrile	318.15	-	2790.6	[147]
Acetonitrile	323.15	-	3026.7	[146]
Acetonitrile	323.15	-	3762.1	[147]
Dichloromethane	278.15	-	32.46	[148]
Dichloromethane	283.15	-	40.77	[148]
Dichloromethane	288.15	-	51.35	[148]
Dichloromethane	293.15	-	62.75	[148]
Dichloromethane	298.15	-	79.19	[148]
Dichloromethane	303.15	-	96.86	[148]
Dichloromethane	308.15	-	118.6	[148]
Dimethyl sulfoxide	293.15	-	2971.0	[148]
Dimethyl sulfoxide	298.15	-	3086.3	[148]
Dimethyl sulfoxide	303.15	-	3214.6	[148]
Dimethyl sulfoxide	308.15	-	3385.1	[148]
Dimethyl sulfoxide	313.15	-	3534.1	[148]
Dimethyl sulfoxide	318.15	-	3737.0	[148]
Dimethyl sulfoxide	323.15	-	3970.0	[148]
Dimethylformamide	278.15	-	2250.0	[148]
Dimethylformamide	283.15	-	2322.4	[148]
Dimethylformamide	288.15	-	2408.4	[148]
Dimethylformamide	293.15	-	2490.0	[148]
Dimethylformamide	298.15	-	2595.0	[148]
Dimethylformamide	303.15	-	2715.2	[148]
Dimethylformamide	308.15	-	2856.1	[148]
Dimethylformamide	313.15	-	3012.2	[148]
Dimethylformamide	318.15	-	3175.2	[148]
Dimethylformamide	323.15	-	3395.9	[148]
Ethanol	278.15	-	182.6	[146]
Ethanol	278.15	-	254.6	[147]
Ethanol	278.15	-	167.2	[148]
Ethanol	283.15	-	217.6	[146]
Ethanol	283.15	-	281.6	[147]
Ethanol	283.15	-	202.5	[148]
Ethanol	288.15	-	262.0	[146]
Ethanol	288.15	-	319.9	[147]
Ethanol	288.15	-	251.8	[148]
Ethanol	293.15	-	311.2	[146]
Ethanol	293.15	-	361.4	[147]
Ethanol	293.15	-	294.6	[148]
Ethanol	298.15	-	370.0	[146]
Ethanol	298.15	-	408.0	[147]
Ethanol	298.15	-	353.7	[148]
Ethanol	303.15	-	439.3	[146]
Ethanol	303.15	-	467.5	[147]
Ethanol	303.15	-	423.7	[148]
Ethanol	308.15	-	518.4	[146]
Ethanol	308.15	-	529.7	[147]
Ethanol	308.15	-	505.2	[148]
Ethanol	313.15	-	606.9	[146]
Ethanol	313.15	-	615.3	[147]
Ethanol	313.15	-	604.5	[148]
Ethanol	318.15	-	722.6	[146]
Ethanol	318.15	-	707.9	[147]
Ethanol	318.15	-	720.8	[148]
Ethanol	323.15	-	847.7	[146]
Ethanol	323.15	-	832.3	[147]
Ethanol	323.15	-	858.6	[148]
Ethyl acetate	278.15	-	553.6	[147]
Ethyl acetate	278.15	-	319.1	[148]
Ethyl acetate	283.15	-	618.0	[147]
Ethyl acetate	283.15	-	351.2	[148]
Ethyl acetate	288.15	-	671.9	[147]
Ethyl acetate	288.15	-	384.9	[148]
Ethyl acetate	293.15	-	731.6	[147]
Ethyl acetate	293.15	-	425.9	[148]
Ethyl acetate	298.15	-	824.2	[147]
Ethyl acetate	298.15	-	469.4	[148]
Ethyl acetate	303.15	-	909.6	[147]
Ethyl acetate	303.15	-	514.4	[148]
Ethyl acetate	308.15	-	1016.7	[147]
Ethyl acetate	308.15	-	565.3	[148]
Ethyl acetate	313.15	-	1122.8	[147]
Ethyl acetate	313.15	-	630.3	[148]
Ethyl acetate	318.15	-	1286.7	[147]
Ethyl acetate	318.15	-	702.5	[148]
Ethyl acetate	323.15	-	1463.0	[147]
Ethyl acetate	323.15	-	786.2	[148]
Ethylene Glycol	278.15	-	4.45	[148]
Ethylene Glycol	283.15	-	5.789	[148]
Ethylene Glycol	288.15	-	7.47	[148]
Ethylene Glycol	293.15	-	9.68	[148]
Ethylene Glycol	298.15	-	11.93	[148]
Ethylene Glycol	303.15	-	15.21	[148]
Ethylene Glycol	308.15	-	19.2	[148]
Ethylene Glycol	313.15	-	24.14	[148]
Ethylene Glycol	318.15	-	29.92	[148]
Ethylene Glycol	323.15	-	37.12	[148]
Glycol monoethyl ether	278.15	-	441.8	[148]
Glycol monoethyl ether	283.15	-	477.1	[148]
Glycol monoethyl ether	288.15	-	516.1	[148]
Glycol monoethyl ether	293.15	-	558.8	[148]
Glycol monoethyl ether	298.15	-	607.5	[148]
Glycol monoethyl ether	303.15	-	660.0	[148]
Glycol monoethyl ether	308.15	-	720.7	[148]
Glycol monoethyl ether	313.15	-	789.1	[148]
Glycol monoethyl ether	318.15	-	864.6	[148]
Glycol monoethyl ether	323.15	-	959.1	[148]
Isobutanol	278.15	-	96.17	[147]
Isobutanol	283.15	-	119.6	[147]
Isobutanol	288.15	-	153.8	[147]
Isobutanol	293.15	-	201.7	[147]
Isobutanol	298.15	-	250.0	[147]
Isobutanol	303.15	-	316.1	[147]
Isobutanol	308.15	-	394.6	[147]
Isobutanol	313.15	-	482.1	[147]
Isobutanol	318.15	-	603.2	[147]
Isobutanol	323.15	-	756.3	[147]
Isopropanol	278.15	-	227.2	[146]
Isopropanol	278.15	-	209.0	[147]
Isopropanol	283.15	-	259.5	[146]
Isopropanol	283.15	-	237.0	[147]
Isopropanol	288.15	-	297.0	[146]
Isopropanol	288.15	-	269.8	[147]
Isopropanol	293.15	-	340.3	[146]
Isopropanol	293.15	-	313.8	[147]
Isopropanol	298.15	-	389.7	[146]
Isopropanol	298.15	-	362.8	[147]
Isopropanol	303.15	-	442.3	[146]
Isopropanol	303.15	-	420.4	[147]
Isopropanol	308.15	-	506.4	[146]
Isopropanol	308.15	-	488.4	[147]
Isopropanol	313.15	-	575.0	[146]
Isopropanol	313.15	-	570.1	[147]
Isopropanol	318.15	-	646.4	[146]
Isopropanol	318.15	-	672.9	[147]
Isopropanol	323.15	-	748.0	[146]
Isopropanol	323.15	-	776.8	[147]
Methanol	278.15	-	289.6	[147]
Methanol	278.15	-	212.0	[148]
Methanol	283.15	-	340.0	[147]
Methanol	283.15	-	259.5	[148]
Methanol	288.15	-	403.0	[147]
Methanol	288.15	-	320.2	[148]
Methanol	293.15	-	466.9	[147]
Methanol	293.15	-	383.4	[148]
Methanol	298.15	-	554.9	[147]
Methanol	298.15	-	471.3	[148]
Methanol	303.15	-	648.4	[147]
Methanol	303.15	-	570.2	[148]
Methanol	308.15	-	765.4	[147]
Methanol	308.15	-	688.9	[148]
Methanol	313.15	-	911.1	[147]
Methanol	313.15	-	821.9	[148]
Methanol	318.15	-	1094.7	[147]
Methanol	318.15	-	993.7	[148]
Methanol	323.15	-	1309.5	[147]
Methanol	323.15	-	1190.2	[148]
Methyl acetate	278.15	-	581.5	[147]
Methyl acetate	278.15	-	370.8	[148]
Methyl acetate	283.15	-	659.0	[147]
Methyl acetate	283.15	-	405.4	[148]
Methyl acetate	288.15	-	765.6	[147]
Methyl acetate	288.15	-	448.3	[148]
Methyl acetate	293.15	-	913.7	[147]
Methyl acetate	293.15	-	487.7	[148]
Methyl acetate	298.15	-	1089.2	[147]
Methyl acetate	298.15	-	539.7	[148]
Methyl acetate	303.15	-	1305.0	[147]
Methyl acetate	303.15	-	575.9	[148]
Methyl acetate	308.15	-	1547.6	[147]
Methyl acetate	308.15	-	649.9	[148]
Methyl acetate	313.15	-	1823.7	[147]
Methyl acetate	313.15	-	718.4	[148]
Methyl acetate	318.15	-	2196.6	[147]
Methyl acetate	318.15	-	797.0	[148]
Methyl acetate	323.15	-	2693.0	[147]
Methyl acetate	323.15	-	888.8	[148]
Tetrahydrofuran	278.15	-	1208.6	[147]
Tetrahydrofuran	283.15	-	1314.5	[147]
Tetrahydrofuran	288.15	-	1447.4	[147]
Tetrahydrofuran	293.15	-	1604.5	[147]
Tetrahydrofuran	298.15	-	1804.2	[147]
Tetrahydrofuran	303.15	-	2022.3	[147]
Tetrahydrofuran	308.15	-	2271.0	[147]
Tetrahydrofuran	313.15	-	2563.2	[147]
Tetrahydrofuran	318.15	-	2913.7	[147]
Tetrahydrofuran	323.15	-	3300.2	[147]
Water	278.15	-	0.0037	[146]
Water	283.15	-	0.0049	[146]
Water	288.15	-	0.0062	[146]
Water	293.15	-	0.008	[146]
Water	298.15	-	0.0102	[146]
Water	303.15	-	0.0128	[146]
Water	308.15	-	0.0163	[146]
Water	313.15	-	0.0201	[146]
Water	318.15	-	0.0251	[146]
Water	323.15	-	0.0312	[146]

Molecule 3D descriptors

Descriptor	Value
PMI1	660.0505
PMI2	2919.0773
PMI3	3381.2035
NPR1	0.1952
NPR2	0.8633
RadiusOfGyration	3.5496
InertialShapeFactor	0.0013
Eccentricity	0.9808
Asphericity	0.5252
SpherocityIndex	0.1064
PBF	0.5534