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    Nilutamide

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

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    2D Structure
    Also known as: 63612-50-0, Anandron, Nilandron, 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)imidazolidine-2,4-dione, Ru-23908, Nilutamida
    Molecular Formula
    C12H10F3N3O4
    Molecular Weight
    317.22  g/mol
    InChI Key
    XWXYUMMDTVBTOU-UHFFFAOYSA-N
    FDA UNII
    51G6I8B902
    Nilutamide is a synthetic, nonsteroidal agent with antiandrogenic properties. Nilutamide preferentially binds to androgen receptors and blocks androgen receptor activation by testosterone and other androgens; this agent may inhibit androgen-dependent growth of normal and neoplastic prostate cells. (NCI04)
    Nilutamide is an Androgen Receptor Inhibitor. The mechanism of action of nilutamide is as an Androgen Receptor Antagonist.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
    2.1.2 InChI
    InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)
    2.1.3 InChI Key
    XWXYUMMDTVBTOU-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1(C(=O)N(C(=O)N1)C2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C
    2.2 Other Identifiers
    2.2.1 UNII
    51G6I8B902
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)- 2,4-imidazolidinedione

    2. Anandron

    3. Nilandron

    4. Ru 23908

    5. Ru 23908-10

    6. Ru-23908

    2.3.2 Depositor-Supplied Synonyms

    1. 63612-50-0

    2. Anandron

    3. Nilandron

    4. 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)imidazolidine-2,4-dione

    5. Ru-23908

    6. Nilutamida

    7. Nilutamidum

    8. 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione

    9. Ru 23908

    10. 5,5-dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoin

    11. Nilandrone

    12. Nilandron;ru 23908

    13. Nsc-758683

    14. Chembl1274

    15. Chebi:7573

    16. Nilutamidum [latin]

    17. Nilutamida [spanish]

    18. 2,4-imidazolidinedione,5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-

    19. 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-2,4-imidazolidinedione

    20. 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedione

    21. 2,4-imidazolidinedione, 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-

    22. 51g6i8b902

    23. Ncgc00015754-08

    24. Cas-63612-50-0

    25. Dsstox_cid_14165

    26. Dsstox_rid_79118

    27. Dsstox_gsid_34165

    28. Nilutamide [usan:inn:ban]

    29. 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)-phenyl)imidazolidine-2,4-dione

    30. Nilandron (tn)

    31. Ru 23908-10

    32. Sr-01000076034

    33. Nilutamide (usan/inn)

    34. Brn 0841906

    35. Unii-51g6i8b902

    36. Nilutamide, Solid

    37. 2,4-imidazolidinedione, 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-

    38. 1-(3'-trifluoromethyl-4'-nitrophenyl)-4,4-dimethylimidazolidine-2,5-dione

    39. Mfcd00864670

    40. Spectrum_001625

    41. Tocris-1759

    42. Nilutamide [mi]

    43. Specplus_000902

    44. Nilutamide [inn]

    45. Prestwick0_000928

    46. Prestwick1_000928

    47. Prestwick2_000928

    48. Prestwick3_000928

    49. Spectrum2_001973

    50. Spectrum3_001633

    51. Spectrum4_000600

    52. Spectrum5_001512

    53. Lopac-n-8534

    54. Nilutamide [usan]

    55. Nilutamide [vandf]

    56. N 8534

    57. Nilutamide [mart.]

    58. Nilutamide [usp-rs]

    59. Nilutamide [who-dd]

    60. Bidd:pxr0177

    61. Lopac0_000879

    62. Schembl12670

    63. Bspbio_000836

    64. Bspbio_003325

    65. Kbiogr_001100

    66. Kbioss_002105

    67. Mls002154066

    68. Bidd:gt0683

    69. Divk1c_006998

    70. Spectrum1504152

    71. Spbio_002125

    72. Spbio_003015

    73. Bpbio1_000920

    74. Gtpl2864

    75. Dtxsid3034165

    76. Nilutamide [orange Book]

    77. Kbio1_001942

    78. Kbio2_002105

    79. Kbio2_004673

    80. Kbio2_007241

    81. Kbio3_002545

    82. Nilutamide [ep Monograph]

    83. Bcpp000148

    84. Hms1570j18

    85. Hms1922f03

    86. Hms2093a10

    87. Hms2097j18

    88. Hms2230e03

    89. Hms3262p19

    90. Hms3268c18

    91. Hms3369i02

    92. Hms3414n15

    93. Hms3678n13

    94. Hms3714j18

    95. Nilutamide [usp Monograph]

    96. Pharmakon1600-01504152

    97. Amy32529

    98. Bcp26617

    99. Zinc3874498

    100. Tox21 110213

    101. Tox21_110213

    102. Tox21_301589

    103. Tox21_500879

    104. Bdbm50135912

    105. Ccg-39427

    106. Nsc758683

    107. S4836

    108. Stk633161

    109. Akos005565152

    110. Akos025147305

    111. Tox21_110213_1

    112. Ac-5260

    113. Bcp9000990

    114. Db00665

    115. Lp00879

    116. Nsc 758683

    117. Ru23908

    118. Sb19036

    119. Sdccgsbi-0050854.p004

    120. 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-1,3-diazolidine-2,4-dione

    121. Ncgc00015754-01

    122. Ncgc00015754-02

    123. Ncgc00015754-03

    124. Ncgc00015754-04

    125. Ncgc00015754-05

    126. Ncgc00015754-06

    127. Ncgc00015754-07

    128. Ncgc00015754-09

    129. Ncgc00015754-10

    130. Ncgc00015754-11

    131. Ncgc00015754-12

    132. Ncgc00015754-15

    133. Ncgc00015754-16

    134. Ncgc00015754-22

    135. Ncgc00025280-01

    136. Ncgc00025280-02

    137. Ncgc00025280-03

    138. Ncgc00025280-04

    139. Ncgc00025280-05

    140. Ncgc00025280-06

    141. Ncgc00025280-07

    142. Ncgc00025280-08

    143. Ncgc00255271-01

    144. Ncgc00261564-01

    145. As-14123

    146. Bn166184

    147. Hy-13702

    148. Smr001233381

    149. Sbi-0050854.p003

    150. Ab00053180

    151. Cs-0007719

    152. Eu-0100879

    153. Ft-0630740

    154. N1212

    155. C08164

    156. D00965

    157. Ab00053180_07

    158. 612n500

    159. A834440

    160. L000759

    161. Q3877030

    162. Ru-23908;ru 23908;ru23908

    163. Sr-01000076034-1

    164. Sr-01000076034-3

    165. Sr-01000076034-5

    166. Sr-01000076034-6

    167. Sr-01000076034-9

    168. Brd-k23566484-001-05-2

    169. Brd-k23566484-001-09-4

    170. Z2417927201

    171. Nilutamide, European Pharmacopoeia (ep) Reference Standard

    172. 1-(3'-trifluoromethyl-4'-nitrophenyl)-4,4-dimethyl-imidazoline-2,5-dione

    173. 1-(3'-trifluoromethyl-4'-nitrophenyl)4,4-dimethyl-imidazoline-2,5-dione

    174. 1-(3'-trifluoromethyl-4'nitrophenyl)-4,4-dimethyl-imidazoline-2,5-dione

    175. 1-(3'trifluoromethyl-4'-nitropheyl)-4,4-dimethyl-imidazoline-2,5-dione

    176. 1-(3-'trifluoromethyl-4'-nitrophenyl)-4,4-dimethyl-imidazoline-2,5-dione

    177. 1-(3-trifluoromethyl-4-nitro-phenyl)-4,4-dimethyl Imidazolidine-2,5-dione

    178. 1-(3-trifluoromethyl-4-nitro-phenyl)-4,4-dimethyl-imidazolidine-2,5-dione

    179. 1-(3-trifluoromethyl-4-nitro-phenyl)-4,4-dimethyl-imidazoline-2,5-dione

    180. 1-(3-trifluoromethyl-4-nitrophenyl)-4,4-dimethyl-imidazoline-2,5-dione

    181. 3-(3-(trifluoromethyl)-4-nitrophenyl)-5,5-dimethylimidazolidine-2,4-dione

    182. 5,5-dimethyl-3-(4-nitro-3-trifluoromethyl-phenyl)-imidazolidine-2,4-dione

    183. Diethyl1,4-dihydro-2,6-dimethyl-1,4-diphenyl-3,5-pyridinedicarboxylate

    184. 5,5-dimethyl-3-(.alpha.,.alpha.,.alpha.-trifluoro-4-nitro-m-tolyl)hydantoin

    185. 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-imidazolidine-2,4-dione

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 317.22 g/mol
    Molecular Formula C12H10F3N3O4
    XLogP32
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count1
    Exact Mass317.06234029 g/mol
    Monoisotopic Mass317.06234029 g/mol
    Topological Polar Surface Area95.2 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity515
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameNilandron
    PubMed HealthNilutamide (By mouth)
    Drug ClassesAntiandrogen
    Drug LabelNILANDRON tablets contain nilutamide, a nonsteroidal, orally active antiandrogen having the chemical name 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedione with the following structural formula:Nilutamide is a microcrystalli...
    Active IngredientNilutamide
    Dosage FormTablet
    RouteOral
    Strength150mg
    Market StatusPrescription
    CompanyCovis Pharma Sarl

    2 of 2  
    Drug NameNilandron
    PubMed HealthNilutamide (By mouth)
    Drug ClassesAntiandrogen
    Drug LabelNILANDRON tablets contain nilutamide, a nonsteroidal, orally active antiandrogen having the chemical name 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedione with the following structural formula:Nilutamide is a microcrystalli...
    Active IngredientNilutamide
    Dosage FormTablet
    RouteOral
    Strength150mg
    Market StatusPrescription
    CompanyCovis Pharma Sarl

    4.2 Drug Indication

    For use in combination with surgical castration for the treatment of metastatic prostate cancer involving distant lymph nodes, bone, or visceral organs (Stage D2).

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Nilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration. The relative binding affinity of nilutamide at the androgen receptor is less than that of bicalutamide, but similar to that of hydroxuflutamide.

    5.2 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Androgen Antagonists

    Compounds which inhibit or antagonize the biosynthesis or actions of androgens. (See all compounds classified as Androgen Antagonists.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    NILUTAMIDE
    5.3.2 FDA UNII
    51G6I8B902
    5.3.3 Pharmacological Classes
    Androgen Receptor Inhibitor [EPC]; Androgen Receptor Antagonists [MoA]
    5.4 ATC Code

    L - Antineoplastic and immunomodulating agents

    L02 - Endocrine therapy

    L02B - Hormone antagonists and related agents

    L02BB - Anti-androgens

    L02BB02 - Nilutamide

    5.5 Absorption, Distribution and Excretion

    Absorption

    Rapidly and completely absorbed, yielding high and persistent plasma concentrations.

    Route of Elimination

    Nilutamide is extensively metabolized andless than 2% of the drug is excreted unchanged in urine after 5 days. Fecal elimination is negligible, ranging from 1.4% to 7% of the dose after 4 to 5 days.

    5.6 Metabolism/Metabolites

    The results of a human metabolism study using 14C-radiolabelled tablets show that nilutamide is extensively metabolized and less than 2% of the drug is excreted unchanged in urine after 5 days.

    5.7 Biological Half-Life

    38.0-59.1 hours

    5.8 Mechanism of Action

    Nilutamide competes with androgen for the binding of androgen receptors, consequently blocking the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. This blockade of androgen receptors may result in growth arrest or transient tumor regression through inhibition of androgen-dependent DNA and protein synthesis.