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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.