Drug

D0062 | Flutamide

Molecular Formula C11H11F3N2O3
Molecular Weight 276.21
Structure
State solid
Route of elimination Flutamide and its metabolites are excreted mainly in the urine with only 4.2% of a single dose excreted in the feces over 72 hours.
Protein binding 94-96%
Half life The plasma half-life for the alpha-hydroxylated metabolite of flutamide (an active metabolite) is approximately 6 hours.
Absorption Rapidly and completely absorbed.
Trade names Eulexin
Description nonsteroidal antiandrogen (NSAA)

L

L02BB01 Flutamide


[L02BB] Anti-androgens


[L02B] HORMONE ANTAGONISTS AND RELATED AGENTS


[L02] ENDOCRINE THERAPY


[L] Antineoplastic and immunomodulating agents


Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 27 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. Negative EC20 36
RESPIRATION ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
OXYGEN CONSUMPTION RATE (OCR) > 100 μM 2 minutes human HepG2 Measurement of OCR decrease EC50 7
ELECTRON TRANSPORT CHAIN decrease 35
ELECTRON TRANSPORT CHAIN decrease 41
ECAR > 100 μM 2 minutes human HepG2 Measurement of ECAR increase EC50 7
GLUCOSE GALACTOSE IC50 RATIO 300.0 ± 0, 183.3 ± 2.9, 1.6, 300.0 ± 0, 205.3 ± 82.4 ,1.6 4hr H9c2 cells high-glucose–galactose cell viability assay with JC-1 mitochondrial membrane potential and ATP-depletion assays (CellTiter-Glo reagent ). Negative glucose/galactose IC50 ratio (JC-1 IC50 in glucose, JC-1 IC50 in galactose, JC-1 glu/gla, ATP IC50 in glucose, ATP IC50 in galactose, ATP glu/gla ) 50
GLUCOSE GALACTOSE IC50 RATIO 300.0 ± 0, 78.3 ± 24.8, 4.1, 266 ± 58.9 , 62.6 ± 27.3, 5 24hr H9c2 cells high-glucose–galactose cell viability assay with JC-1 mitochondrial membrane potential and ATP-depletion assays (CellTiter-Glo reagent ). glucose/galactose IC50 ratio (JC-1 IC50 in glucose, JC-1 IC50 in galactose, JC-1 glu/gla, ATP IC50 in glucose, ATP IC50 in galactose, ATP glu/gla ) 50
SWELLING > 800 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase inhibitor 35
NADH:ubiquinone reductase inhibitor 41
NADH:ubiquinone reductase ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. Negative EC20 36
Succinate dehydrogenase ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
Cytochrome c > 400 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 66 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H302 (83.33%): Harmful if swallowed [Warning Acute toxicity, oral]


H312 (66.67%): Harmful in contact with skin [Warning Acute toxicity, dermal]


H332 (72.73%): Harmful if inhaled [Warning Acute toxicity, inhalation]


H360 (19.7%): May damage fertility or the unborn child [Danger Reproductive toxicity]


H361 (77.27%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H373 (18.18%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]


H413 (15.15%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P314, P322, P330, P363, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Danger

H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]


H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]


P201, P202, P260, P264, P270, P273, P281, P308+P313, P314, P391, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Benign prostatic hyperplasia

  • Metastatic neoplasm

  • Neoplasm malignant

  • Prostate cancer metastatic

  • Bladder pain (0.16)

  • Rash (0.08)

  • Diarrhoea

  • Haematuria

  • Rectal haemorrhage

  • .alpha.,.alpha.,.alpha.-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide .alpha.,.alpha.-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide 13311-84-7
    2-Methyl-N-(4-nitro-3-[trifluoromethyl]phenyl)propanamide 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide #
    2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propionamide 3'-Trifluoromethyl-4'-Nitro-Isobutyranilide 311F847
    37209-54-4 4''-nitro-3''-trifluoromethylisobutyranilide 4'-Nitro-3'-(trifluoromethyl)isobutyranilide
    4'-Nitro-3'-trifluoromethylisobutyramilide 4'-Nitro-3'-trifluoromethylisobutyranilide 4-Nitro-3-(trifluoromethyl)isobutyranilide
    76W6J0943E A806562 AB0005010
    AB00052188 AB00052188-09 AB00052188_10
    AB00052188_11 AB02835 AB1010911
    AC-24192 ACMC-20hidt AK499646
    AKOS001025465 AKOS025243203 BCP23006
    BDBM50131270 BPBio1_000087 BRD-K28307902-001-05-0
    BRN 2157663 BSPBio_000079 BSPBio_003122
    C07653 C11H11F3N2O3 CAS-13311-84-7
    CCG-39105 CCRIS 7246 CHEBI:5132
    CHEMBL806 CPD000058187 CS-2359
    CTK4B8363 Cebatrol, veterinary Chimax
    D00586 DB-042163 DB00499
    DSSTox_CID_11121 DSSTox_GSID_32004 DSSTox_RID_78899
    DTXSID7032004 DivK1c_000459 Drogenil
    EINECS 236-341-9 ETHINYL ESTRADIOL) EU-0100557
    Eulexin Eulexin (TN) Eulexine
    F 9397 F0663 FT-0626493
    Flutamid Flutamida Flutamida [INN-Spanish]
    Flutamide (Eulexin) Flutamide (JP17/USP/INN) Flutamide (pubertal study)
    Flutamide USP25 Flutamide [USAN:BAN:INN] Flutamide [USAN:USP:INN:BAN]
    Flutamide for system suitability, European Pharmacopoeia (EP) Reference Standard Flutamide(Eulexin) Flutamide, European Pharmacopoeia (EP) Reference Standard
    Flutamide, United States Pharmacopeia (USP) Reference Standard Flutamide, certified reference material, TraceCERT(R) Flutamide,(S)
    Flutamidum Flutamidum [INN-Latin] Flutamin
    GTPL6943 HMS1568D21 HMS1921O16
    HMS2090I18 HMS2092O14 HMS2095D21
    HMS2230P19 HMS3259I03 HMS3261P15
    HMS3373C12 HMS3655G22 HMS3712D21
    HMS501G21 HY-B0022 Ham's F-12 medium
    IDI1_000459 J10037 K-4175
    KBio1_000459 KBio2_001690 KBio2_004258
    KBio2_006826 KBio3_002342 KBioGR_001377
    KBioSS_001690 KS-00000L22 KS-5091
    LP00557 LS-2105 Lopac-F-9397
    Lopac0_000557 MCULE-7498839065 METHOXYCHLOR
    MFCD00072009 MKXKFYHWDHIYRV-UHFFFAOYSA-N MLS000069634
    MLS001065596 MLS002548892 N-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)ISOBUTYRAMIDE
    N1-[4-nitro-3-(trifluoromethyl)phenyl]-2-methylpropanamide NC00451 NCGC00015452-01
    NCGC00015452-02 NCGC00015452-03 NCGC00015452-04
    NCGC00015452-05 NCGC00015452-06 NCGC00015452-07
    NCGC00015452-08 NCGC00015452-09 NCGC00015452-10
    NCGC00015452-11 NCGC00015452-12 NCGC00015452-13
    NCGC00015452-14 NCGC00015452-15 NCGC00015452-16
    NCGC00015452-19 NCGC00015452-20 NCGC00091460-01
    NCGC00091460-02 NCGC00091460-03 NCGC00091460-04
    NCGC00091460-05 NCGC00091460-06 NCGC00091460-07
    NCGC00091460-08 NCGC00091460-09 NCGC00254495-01
    NCGC00259718-01 NCGC00261242-01 NFBA
    NINDS_000459 NK-601 NSC 215876
    NSC-147834 NSC-215876 NSC-757817
    NSC147834 NSC215876 NSC757817
    Niftholide Niftolide Odyne
    PUBERTAL FLUTAMIDE STUDY (PUBERTAL STUDIES OF VINCLOZOLIN Pharmakon1600-01500995 Prestwick0_000180
    Prestwick1_000180 Prestwick2_000180 Prestwick3_000180
    Prestwick_228 Propanamide, 2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)- Propanamide, 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-
    Propanamide,2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]- Prostandril PubChem13536
    Q-201131 Q418669 SAM002264612
    SBB006930 SBI-0050540.P003 SC-12180
    SCH13521 SCHEMBL12932289 SCHEMBL3934
    SMR000058187 SPBio_000982 SPBio_002000
    SPECTRUM1500995 SR-01000075888 SR-01000075888-1
    SR-01000075888-6 SR-01000075888-7 SR-01000075888-9
    ST058409 SW196536-4 Sch 13521
    Sch-13521 Spectrum2_001201 Spectrum3_001421
    Spectrum4_000829 Spectrum5_001450 Spectrum_001210
    Tox21_110154 Tox21_110154_1 Tox21_202169
    Tox21_300536 Tox21_500557 UNII-76W6J0943E
    Z56755651 ZINC3812944 a,a,a-Trifluoro-2-methyl-4'-nitro- m-propionotoluidide
    alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide alpha,alpha,alpha-trifluoro-2-methyl-4''-nitro-m-propionotoluidide flutamide
    m-Propionotoluidide, .alpha.,.alpha.,.alpha.-trifluoro-2-methyl-4'-nitro- m-Propionotoluidide, 2-methyl-4'-nitro-.alpha.,.alpha.,.alpha.-trifluoro- m-Propionotoluidide, 2-methyl-4'-nitro-alpha,alpha,alpha-triflouro-
    m-Propionotoluidide, alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro- m-Propionotoluidide, alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro- (8CI) m-Propionotoluidide,.alpha.,.alpha.-trifluoro-
    m-Propionotoluidide,.alpha.,.alpha.-trifluoro-2-methyl-4'-nitro- m-propionotoluidide,alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro niftolid
    s1908

    DrugBank Name Flutamide
    DrugBank DB00499
    CAS Number 13311-84-7, 37209-54-4
    PubChem Compound 3397
    KEGG Compound ID C07653
    KEGG Drug D00586
    PubChem.Substance 46508874
    ChEBI 5132
    PharmGKB PA449685
    ChemSpider 3280
    BindingDB 50131270.0
    TTD DAP000301
    Wikipedia Flutamide
    HET HFT
    DPD 1847

    1. Dykens et al. (2007)