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Chemistry

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Also known as: 13311-84-7, Eulexin, Niftolide, Niftholide, Sch 13521, 2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

Molecular Formula

C₁₁H₁₁F₃N₂O₃

Molecular Weight

276.21 g/mol

InChI Key

MKXKFYHWDHIYRV-UHFFFAOYSA-N

FDA UNII

76W6J0943E

An antiandrogen with about the same potency as cyproterone in rodent and canine species.

Flutamide is an Androgen Receptor Inhibitor. The mechanism of action of flutamide is as an Androgen Receptor Antagonist.

1 2D Structure

Flutamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

2.1.2 InChI

InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)

2.1.3 InChI Key

MKXKFYHWDHIYRV-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F

2.2 Other Identifiers

2.2.1 UNII

76W6J0943E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Apimid

2. Apo Flutamide

3. Apo-flutamide

4. Apoflutamide

5. Chimax

6. Cytamid

7. Drogenil

8. Euflex

9. Eulexin

10. Eulexine

11. Fluken

12. Flulem

13. Flumid

14. Fluta 1a Pharma

15. Fluta Cell

16. Fluta Gry

17. Fluta-cell

18. Fluta-gry

19. Flutacell

20. Flutagry

21. Flutamin

22. Flutandrona

23. Flutaplex

24. Flutexin

25. Fugerel

26. Grisetin

27. Niftolid

28. Niftolide

29. Novo Flutamide

30. Novo-flutamide

31. Novoflutamide

32. Oncosal

33. Pms Flutamide

34. Pms-flutamide

35. Prostacur

36. Prostica

37. Prostogenat

38. Sch 13521

39. Sch-13521

40. Sch13521

41. Testotard

2.3.2 Depositor-Supplied Synonyms

1. 13311-84-7

2. Eulexin

3. Niftolide

4. Niftholide

5. Sch 13521

6. 2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

7. Nfba

8. Niftolid

9. Drogenil

10. Flutamin

11. Cebatrol, Veterinary

12. Flutamida

13. Flutamidum

14. Sch-13521

15. 4'-nitro-3'-trifluoromethylisobutyranilide

16. 2-methyl-n-(4-nitro-3-[trifluoromethyl]phenyl)propanamide

17. N-(4-nitro-3-(trifluoromethyl)phenyl)isobutyramide

18. Sch13521

19. Mfcd00072009

20. Nsc 215876

21. Flutamide (eulexin)

22. Alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro-m-propionotoluidide

23. Chembl806

24. Propanamide, 2-methyl-n-(4-nitro-3-(trifluoromethyl)phenyl)-

25. Propanamide, 2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]-

26. Nsc-215876

27. 4-nitro-3-(trifluoromethyl)isobutyranilide

28. Chebi:5132

29. 76w6j0943e

30. Ncgc00015452-09

31. Eulexine

32. Chimax

33. 4'-nitro-3'-trifluoromethylisobutyramilide

34. Cas-13311-84-7

35. Ham's F-12 Medium

36. Flutamidum [inn-latin]

37. Dsstox_cid_11121

38. Dsstox_rid_78899

39. Dsstox_gsid_32004

40. Flutamida [inn-spanish]

41. Flutamide Usp25

42. N-[4-nitro-3-(trifluoromethyl)phenyl]isobutyramide

43. Prostandril

44. Odyne

45. .alpha.,.alpha.,.alpha.-trifluoro-2-methyl-4'-nitro-m-propionotoluidide

46. Smr000058187

47. Eulexin (tn)

48. Ccris 7246

49. M-propionotoluidide,.alpha.,.alpha.-trifluoro-

50. Sr-01000075888

51. 4'-nitro-3'-(trifluoromethyl)isobutyranilide

52. Einecs 236-341-9

53. Brn 2157663

54. .alpha.,.alpha.-trifluoro-2-methyl-4'-nitro-m-propionotoluidide

55. M-propionotoluidide,.alpha.,.alpha.-trifluoro-2-methyl-4'-nitro-

56. Unii-76w6j0943e

57. Flutamide [usan:usp:inn:ban]

58. Flutamide,(s)

59. Prestwick_228

60. Nk-601

61. Spectrum_001210

62. 2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]propionamide

63. Cpd000058187

64. Flutamide [inn]

65. Flutamide [jan]

66. Flutamide [mi]

67. Flutamide [usan]

68. Prestwick0_000180

69. Prestwick1_000180

70. Prestwick2_000180

71. Prestwick3_000180

72. Spectrum2_001201

73. Spectrum3_001421

74. Spectrum4_000829

75. Spectrum5_001450

76. Lopac-f-9397

77. F0663

78. Flutamide (pubertal Study)

79. Flutamide [mart.]

80. F 9397

81. Flutamide [usp-rs]

82. Flutamide [who-dd]

83. Schembl3934

84. Lopac0_000557

85. Bspbio_000079

86. Bspbio_003122

87. Kbiogr_001377

88. Kbioss_001690

89. Mls000069634

90. Mls001065596

91. Mls002548892

92. Divk1c_000459

93. Spectrum1500995

94. Spbio_000982

95. Spbio_002000

96. Flutamide (jp17/usp/inn)

97. Bpbio1_000087

98. Gtpl6943

99. Flutamide [ep Impurity]

100. Flutamide [orange Book]

101. Chembl4759307

102. Dtxsid7032004

103. Flutamide [ep Monograph]

104. Schembl12932289

105. Hms501g21

106. Kbio1_000459

107. Kbio2_001690

108. Kbio2_004258

109. Kbio2_006826

110. Kbio3_002342

111. Flutamide [usp Monograph]

112. Ninds_000459

113. Hms1568d21

114. Hms1921o16

115. Hms2090i18

116. Hms2092o14

117. Hms2095d21

118. Hms2230p19

119. Hms3259i03

120. Hms3261p15

121. Hms3373c12

122. Hms3655g22

123. Hms3712d21

124. Pharmakon1600-01500995

125. Amy32524

126. Bcp23006

127. Hy-b0022

128. Zinc3812944

129. Tox21_110154

130. Tox21_202169

131. Tox21_300536

132. Tox21_500557

133. Bdbm50131270

134. Ccg-39105

135. M-propionotoluidide, 2-methyl-4'-nitro-alpha,alpha,alpha-triflouro-

136. M-propionotoluidide, Alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro-

137. Nsc147834

138. Nsc215876

139. Nsc757817

140. S1908

141. Akos001025465

142. Akos025243203

143. M-propionotoluidide, .alpha.,.alpha.,.alpha.-trifluoro-2-methyl-4'-nitro-

144. Tox21_110154_1

145. Ab02835

146. Db00499

147. Ks-5091

148. Lp00557

149. Nc00451

150. Nsc-147834

151. Nsc-757817

152. Sdccgsbi-0050540.p004

153. Idi1_000459

154. Ncgc00015452-01

155. Ncgc00015452-02

156. Ncgc00015452-03

157. Ncgc00015452-04

158. Ncgc00015452-05

159. Ncgc00015452-06

160. Ncgc00015452-07

161. Ncgc00015452-08

162. Ncgc00015452-10

163. Ncgc00015452-11

164. Ncgc00015452-12

165. Ncgc00015452-13

166. Ncgc00015452-14

167. Ncgc00015452-15

168. Ncgc00015452-16

169. Ncgc00015452-19

170. Ncgc00015452-20

171. Ncgc00015452-32

172. Ncgc00091460-01

173. Ncgc00091460-02

174. Ncgc00091460-03

175. Ncgc00091460-04

176. Ncgc00091460-05

177. Ncgc00091460-06

178. Ncgc00091460-07

179. Ncgc00091460-08

180. Ncgc00091460-09

181. Ncgc00254495-01

182. Ncgc00259718-01

183. Ncgc00261242-01

184. Ac-24192

185. Bf166239

186. Sy036411

187. Sbi-0050540.p003

188. Db-042163

189. 3'-trifluoromethyl-4'-nitro-isobutyranilide

190. Ab00052188

191. Eu-0100557

192. Ft-0626493

193. Ft-0668764

194. Sw196536-4

195. 4''-nitro-3''-trifluoromethylisobutyranilide

196. C07653

197. D00586

198. Ab00052188-09

199. Ab00052188_10

200. Ab00052188_11

201. 311f847

202. A806562

203. Q418669

204. Q-201131

205. Sr-01000075888-1

206. Sr-01000075888-6

207. Sr-01000075888-7

208. Sr-01000075888-9

209. Brd-k28307902-001-05-0

210. Flutamide, Certified Reference Material, Tracecert(r)

211. Z56755651

212. A,a,a-trifluoro-2-methyl-4'-nitro- M-propionotoluidide

213. Flutamide, European Pharmacopoeia (ep) Reference Standard

214. 2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide #

215. Flutamide, United States Pharmacopeia (usp) Reference Standard

216. 2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide;flutamide

217. Alpha,alpha,alpha-trifluoro-2-methyl-4''-nitro-m-propionotoluidide

218. M-propionotoluidide, 2-methyl-4'-nitro-.alpha.,.alpha.,.alpha.-trifluoro-

219. Flutamide For System Suitability, European Pharmacopoeia (ep) Reference Standard

220. 37209-54-4

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₁F₃N₂O₃
Molecular Weight	276.21 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	276.07217670 g/mol
Monoisotopic Mass	276.07217670 g/mol
Topological Polar Surface Area	74.9 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	352
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Flutamide
PubMed Health	Flutamide (By mouth)
Drug Classes	Antiandrogen
Drug Label	Flutamide capsules contain flutamide, an acetanilid, nonsteroidal, orally active antiandrogen having the chemical name, ,,-trifluoro-2-methyl-4'-nitrom-propionotoluidide.Each capsule contains 125 mg flutamide. The compound is a buff to yellow p...
Active Ingredient	Flutamide
Dosage Form	Capsule
Route	Oral
Strength	125mg
Market Status	Prescription
Company	Actavis Labs Fl; Par Pharm; Ivax Sub Teva Pharms; Mylan

2 of 2
Drug Name	Flutamide
PubMed Health	Flutamide (By mouth)
Drug Classes	Antiandrogen
Drug Label	Flutamide capsules contain flutamide, an acetanilid, nonsteroidal, orally active antiandrogen having the chemical name, ,,-trifluoro-2-methyl-4'-nitrom-propionotoluidide.Each capsule contains 125 mg flutamide. The compound is a buff to yellow p...
Active Ingredient	Flutamide
Dosage Form	Capsule
Route	Oral
Strength	125mg
Market Status	Prescription
Company	Actavis Labs Fl; Par Pharm; Ivax Sub Teva Pharms; Mylan

4.2 Drug Indication

For the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Flutamide is a nonsteroidal antiandrogen. In animal studies, flutamide demonstrates potent antiandrogenic effects. It exerts its antiandrogenic action by inhibiting androgen uptake and/or by inhibiting nuclear binding of androgen in target tissues or both. Prostatic carcinoma is known to be androgen-sensitive and responds to treatment that counteracts the effect of androgen and/or removes the source of androgen, e.g. castration. Elevations of plasma testosterone and estradiol levels have been noted following flutamide administration.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents, Hormonal

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)

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

FLUTAMIDE

5.3.2 FDA UNII

76W6J0943E

5.3.3 Pharmacological Classes

Androgen Receptor Inhibitor [EPC]; Androgen Receptor Antagonists [MoA]

5.4 ATC Code

L02BB01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02B - Hormone antagonists and related agents

L02BB - Anti-androgens

L02BB01 - Flutamide

5.5 Absorption, Distribution and Excretion

Absorption

Rapidly and completely absorbed.

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.

5.6 Metabolism/Metabolites

Flutamide is rapidly and extensively metabolized, with flutamide comprising only 2.5% of plasma radioactivity 1 hour after administration.

Flutamide has known human metabolites that include 2-hydroxy-flutamide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.7 Biological Half-Life

The plasma half-life for the alpha-hydroxylated metabolite of flutamide (an active metabolite) is approximately 6 hours.

5.8 Mechanism of Action

Flutamide is a nonsteroidal antiandrogen that blocks the action of both endogenous and exogenous testosterone by binding to the androgen receptor. In addition Flutamide is a potent inhibitor of testosterone-stimulated prostatic DNA synthesis. Moreover, it is capable of inhibiting prostatic nuclear uptake of androgen.

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