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Chemistry

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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

Fenretinide
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 Weight 391.5 g/mol
Molecular Formula C26H33NO2
XLogP37.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count6
Exact Mass391.251129295 g/mol
Monoisotopic Mass391.251129295 g/mol
Topological Polar Surface Area49.3 Ų
Heavy Atom Count29
Formal Charge0
Complexity726
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count4
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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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ABOUT THIS PAGE

Fenretinide Manufacturers

A Fenretinide manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Fenretinide, including repackagers and relabelers. The FDA regulates Fenretinide manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Fenretinide API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Fenretinide Suppliers

A Fenretinide supplier is an individual or a company that provides Fenretinide active pharmaceutical ingredient (API) or Fenretinide finished formulations upon request. The Fenretinide suppliers may include Fenretinide API manufacturers, exporters, distributors and traders.

click here to find a list of Fenretinide suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Fenretinide USDMF

A Fenretinide DMF (Drug Master File) is a document detailing the whole manufacturing process of Fenretinide active pharmaceutical ingredient (API) in detail. Different forms of Fenretinide DMFs exist exist since differing nations have different regulations, such as Fenretinide USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Fenretinide DMF submitted to regulatory agencies in the US is known as a USDMF. Fenretinide USDMF includes data on Fenretinide's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Fenretinide USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Fenretinide suppliers with USDMF on PharmaCompass.

Fenretinide NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Fenretinide as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Fenretinide API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Fenretinide as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Fenretinide and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Fenretinide NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Fenretinide suppliers with NDC on PharmaCompass.

Fenretinide GMP

Fenretinide Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Fenretinide GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Fenretinide GMP manufacturer or Fenretinide GMP API supplier for your needs.

Fenretinide CoA

A Fenretinide CoA (Certificate of Analysis) is a formal document that attests to Fenretinide's compliance with Fenretinide specifications and serves as a tool for batch-level quality control.

Fenretinide CoA mostly includes findings from lab analyses of a specific batch. For each Fenretinide CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Fenretinide may be tested according to a variety of international standards, such as European Pharmacopoeia (Fenretinide EP), Fenretinide JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Fenretinide USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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