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Fenretinide

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Also known as: 65646-68-6, N-(4-hydroxyphenyl)retinamide, 4-hpr, 4-hydroxyphenylretinamide, 4-hydroxyphenyl retinamide, Retinoic acid p-hydroxyanilide

Molecular Formula

C₂₆H₃₃NO₂

Molecular Weight

391.5 g/mol

InChI Key

AKJHMTWEGVYYSE-FXILSDISSA-N

FDA UNII

187EJ7QEXL

A synthetic retinoid that is used orally as a chemopreventive against prostate cancer and in women at risk of developing contralateral breast cancer. It is also effective as an antineoplastic agent.

1 2D Structure

Fenretinide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide

2.1.2 InChI

InChI=1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+

2.1.3 InChI Key

AKJHMTWEGVYYSE-FXILSDISSA-N

2.1.4 Canonical SMILES

CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)NC2=CC=C(C=C2)O)C)C

2.1.5 Isomeric SMILES

CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)NC2=CC=C(C=C2)O)/C)/C

2.2 Other Identifiers

2.2.1 UNII

187EJ7QEXL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 13-cis-isomer Fenretinide

2. 4 Hydroxyphenylretinamide

3. 4-hpr

4. 4-hydroxyphenylretinamide

5. Fenretinide, 13 Cis Isomer

6. Fenretinide, 13-cis-isomer

7. Fenretinimide

8. Mcn R 1967

9. Mcn-r-1967

10. Mcnr1967

11. N-(4-hydroxyphenyl)-trans-retinamide

12. N-(4-hydroxyphenyl)retinamide

2.3.2 Depositor-Supplied Synonyms

1. 65646-68-6

2. N-(4-hydroxyphenyl)retinamide

3. 4-hpr

4. 4-hydroxyphenylretinamide

5. 4-hydroxyphenyl Retinamide

6. Retinoic Acid P-hydroxyanilide

7. All-trans-4'-hydroxyretinanilide

8. Mcn-r-1967

9. Fenretinida

10. Fenretinidum

11. 4-hydroxy(phenyl)retinamide

12. N-(4-hydroxyphenyl)all-trans Retinamide

13. Retinamide, N-(4-hydroxyphenyl)-

14. Rii Retinamide

15. Retinoic Acid P-hydroxyphenylamide

16. 4-(hydroxyphenyl)retinamide

17. 15-[(4-hydroxyphenyl)amino]retinal

18. (2e,4e,6e,8e)-n-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide

19. Nsc-760419

20. 187ej7qexl

21. Chembl7301

22. Mls002701698

23. Chebi:42588

24. Nsc-374551

25. Ncgc00090752-03

26. Dsstox_cid_12005

27. Dsstox_rid_78900

28. Dsstox_gsid_32005

29. Fenretinidum [latin]

30. Fenretinida [spanish]

31. 4hpr

32. Fenretinide [usan:inn]

33. Smr001456303

34. Cas-65646-68-6

35. Ccris 3260

36. Sr-01000075917

37. (2e,4e,6e,8e)-n-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide

38. Mfcd00792674

39. Unii-187ej7qexl

40. Brn 5769490

41. Syt-101

42. St-602

43. Fenretinide; 4-hpr

44. Fenretinide (4-hpr)

45. P-hydroxyphenylretinamide

46. Fenretinide [mi]

47. Spectrum5_001939

48. Fenretinide [inn]

49. Fenretinide (usan/inn)

50. Fenretinide [usan]

51. Fenretinide [vandf]

52. Fenretinide [mart.]

53. Lopac0_000625

54. Schembl11703

55. Schembl11704

56. Bspbio_001419

57. Fenretinide [who-dd]

58. Mls001055399

59. Mls006010811

60. Bml2-e08

61. N-(4-hydroxyphenyl)-retinamide

62. Dtxsid2032005

63. Schembl15703189

64. Chebi:92493

65. Amy9087

66. 15-(4-hydroxyanilino)retinal #

67. Hms1361g21

68. Hms1791g21

69. Hms1989g21

70. Hms2089b17

71. Hms3261n12

72. Hms3402g21

73. Hms3412m06

74. Hms3676m06

75. Pharmakon1600-01505602

76. 4-hpr;(4-hydroxyphenyl)retinamide

77. Bcp06908

78. Ex-a4102

79. N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenamide

80. Zinc3871023

81. Tox21_111007

82. Tox21_200989

83. Tox21_500625

84. 1-enyl)nona-2,4,6,8-tetraenamide

85. Bdbm50092055

86. Hsci1_000112

87. Nsc374551

88. Nsc760419

89. S5233

90. Calix[4!-bis-crown-6,95

91. Akos024456572

92. Tox21_111007_1

93. Ccg-204713

94. Cs-0789

95. Db05076

96. Lp00625

97. Mk-4016

98. N-(4-hydroxyphenyl)retinamide, 4-hpr

99. Nsc 760419

100. Sdccgsbi-0050606.p002

101. All-trans-n-(4-hydroxyphenyl)retinamide

102. Dimethyl-9-(2,6,6-trimethylcyclohex-

103. Idi1_033889

104. Retinoic Acid P-hydroxyanilide, >=95%

105. Ncgc00090752-01

106. Ncgc00090752-02

107. Ncgc00090752-04

108. Ncgc00090752-05

109. Ncgc00090752-06

110. Ncgc00090752-07

111. Ncgc00090752-09

112. Ncgc00090752-10

113. Ncgc00090752-11

114. Ncgc00090752-12

115. Ncgc00090752-20

116. Ncgc00258542-01

117. Ncgc00261310-01

118. As-59667

119. Bp-13369

120. Hy-15373

121. Smr000677938

122. Eu-0100625

123. H1464

124. D04162

125. H 7779

126. (2e,4e,6e,8e)-n-(4-hydroxyphenyl)-3,7-

127. Ab00172992-07

128. 646f686

129. A835178

130. Q5443576

131. Sr-01000075917-1

132. Sr-01000075917-4

133. N-(4-hydroxyphenyl)-all-trans-vitamin A Amide

134. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic Acid (4-hydroxy-phenyl)-amide

135. (2e,4e,6e,8e)-n-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenamide

136. (2e,4e,6e,8e)-n-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenamide

137. (2e,4e,6e,8e)-n-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide;fenretinide

138. 2,6,8-nonatetraenamide, N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl-, (all-e)-

139. 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic Acid (4-hydroxy-phenyl)-amide

140. N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraeneamide

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₃NO₂
Molecular Weight	391.5 g/mol
XLogP3	7.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	6
Exact Mass	391.251129295 g/mol
Monoisotopic Mass	391.251129295 g/mol
Topological Polar Surface Area	49.3 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	726
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	4
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in macular degeneration.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anticarcinogenic Agents

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)

Antineoplastic Agents

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

5.2 Metabolism/Metabolites

Fenretinide has known human metabolites that include (2S,3S,4S,5R)-6-[4-[[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

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

5.3 Mechanism of Action

Fenretinide inhibits the growth of several human cancer cell lines, acting through both retinoid-receptor-dependent and retinoid-receptor-independent mechanisms.1In vivo, fenretinide selectively accumulates in breast tissue and is particularly active in inhibiting rat mammary carcinogenesis.1 An important feature of fenretinide is its ability to inhibit cell growth through the induction of apoptosis rather than through differentiation, an effect that is strikingly different from that of vitamin A.1 In contrast to tamoxifen, which inhibits only estrogen receptor (ER)-positive tumors, fenretinide induces apoptosis in both ER-positive and ER-negative breast cancer cell lines.2 All of these properties render fenretinide an attractive candidate for breast cancer chemoprevention.

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