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Prestwick3_000218

Prestwick3_000218

Synopsis, Chemistry

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Also known as: 36330-85-5, Lederfen, Cinopal, Bufemid, Napanol, 4-(4-biphenylyl)-4-oxobutyric acid

Molecular Formula

C₁₆H₁₄O₃

Molecular Weight

254.28 g/mol

InChI Key

ZPAKPRAICRBAOD-UHFFFAOYSA-N

FDA UNII

9815R1WR9B

Fenbufen is a non-steroidal anti-inflammatory drug used primarily to treat inflammation in osteoarthritis, ankylosing spondylitis, and tendinitis. It can also be used to relieve backaches, sprains, and fractures. Fenbufen is available as a capsule or tablet sold with the brand names Cepal, Cinopal, Cybufen, Lederfen, and Reugast. Fenbufen acts by preventing cyclooxygenase from producing prostaglandins which can cause inflammation.

1 2D Structure

Prestwick3_000218

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-oxo-4-(4-phenylphenyl)butanoic acid

2.1.2 InChI

InChI=1S/C16H14O3/c17-15(10-11-16(18)19)14-8-6-13(7-9-14)12-4-2-1-3-5-12/h1-9H,10-11H2,(H,18,19)

2.1.3 InChI Key

ZPAKPRAICRBAOD-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)C2=CC=C(C=C2)C(=O)CCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

9815R1WR9B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cinopal

2. Gamma-oxo(1,1'-biphenyl)-4-butanoic Acid

3. Lederfen

2.3.2 Depositor-Supplied Synonyms

1. 36330-85-5

2. Lederfen

3. Cinopal

4. Bufemid

5. Napanol

6. 4-(4-biphenylyl)-4-oxobutyric Acid

7. 3-(4-phenylbenzoyl)propionic Acid

8. 3-(4-biphenylylcarbonyl)propionic Acid

9. 4-([1,1'-biphenyl]-4-yl)-4-oxobutanoic Acid

10. 4-(biphenyl-4-yl)-4-oxobutanoic Acid

11. Cl-82204

12. Gamma-oxo(1,1'-biphenyl)-4-butanoic Acid

13. 3-(4-biphenylcarbonyl)propionic Acid

14. 4-oxo-4-(4-phenylphenyl)butanoic Acid

15. Cl 82204

16. 4-(4-biphenyl)-4-oxobutyric Acid

17. 4-biphenyl-4-yl-4-oxobutanoic Acid

18. Butyric Acid 4-(4-biphenyl)-4-oxo-

19. Mls000069810

20. Propionic Acid, 3-(4-biphenylylcarbonyl)-

21. Mfcd00056701

22. Nsc-757812

23. Smr000059150

24. Cl 82,204

25. Chembl277522

26. Chebi:31599

27. 9815r1wr9b

28. [1,1'-biphenyl]-4-butanoic Acid, .gamma.-oxo-

29. Fenbufen 100 Microg/ml In Acetonitrile

30. Ncgc00016834-01

31. Cas-36330-85-5

32. Dsstox_cid_3043

33. 4-[1,1'-biphenyl-4-yl]-4-oxobutanoic Acid

34. Dsstox_rid_76849

35. Dsstox_gsid_23043

36. Fenbufenum

37. Cinopol

38. Fenbufene

39. Fenbufene [inn-french]

40. Fenbufenum [inn-latin]

41. Beta,p-phenylbenzoylpropionic Acid

42. 4-{[1,1'-biphenyl]-4-yl}-4-oxobutanoic Acid

43. Sr-01000721906

44. Einecs 252-979-0

45. Brn 2378560

46. Diphenyl-4-gamma-oxo-gamma-butyric Acid

47. (1,1'-biphenyl)-4-butanoic Acid, .gamma.-oxo-

48. Unii-9815r1wr9b

49. Fenbufen [usan:inn:ban:jan]

50. Fenbufen,(s)

51. Prestwick_567

52. (1,1'-biphenyl)-4-butanoic Acid, Gamma-oxo-

53. Fenbufen, 96%

54. Spectrum_001248

55. Fenbufen [usan]

56. Opera_id_464

57. Fenbufen [inn]

58. Fenbufen [jan]

59. Fenbufen [mi]

60. Prestwick0_000218

61. Prestwick1_000218

62. Prestwick2_000218

63. Prestwick3_000218

64. Spectrum2_001389

65. Spectrum3_001430

66. Spectrum4_000411

67. Spectrum5_001528

68. Fenbufen [mart.]

69. Fenbufen [who-dd]

70. Schembl25117

71. Bspbio_000235

72. Bspbio_003140

73. Fenbufen, Analytical Standard

74. Kbiogr_000702

75. Kbioss_001728

76. 3-10-00-03334 (beilstein Handbook Reference)

77. Mls001074090

78. Divk1c_000025

79. Spectrum1501008

80. Spbio_001378

81. Spbio_002156

82. Bpbio1_000259

83. Fenbufen (jp17/usan/inn)

84. Zinc1427

85. Fenbufen [ep Monograph]

86. Dtxsid9023043

87. Hms500b07

88. Kbio1_000025

89. Kbio2_001728

90. Kbio2_004296

91. Kbio2_006864

92. Kbio3_002360

93. Ninds_000025

94. Hms1568l17

95. Hms1921b13

96. Hms2090g14

97. Hms2092b03

98. Hms2095l17

99. Hms2235i24

100. Hms3372m18

101. Hms3712l17

102. Hms3885n06

103. Pharmakon1600-01501008

104. 4-biphenyl-4-yl-4-oxobutyric Acid

105. Bcp12106

106. Hy-b1138

107. .beta.,p-phenylbenzoylpropionic Acid

108. 3-(4-phenyl)benzoyl Propionic Acid

109. Tox21_110638

110. Bdbm50240374

111. Ccg-38988

112. Nsc757812

113. S4526

114. Stk202178

115. 4-biphenyl-4-yl-4-oxo-butyric Acid

116. Akos000200430

117. Tox21_110638_1

118. Cs-4743

119. Db08981

120. Nsc 757812

121. Ss-4225

122. 3-(4'-biphenylcarbonyl) Propanoic Acid

123. Idi1_000025

124. 3-(4-biphenylylcarbonyl) Propionic Acid

125. 3-(4-biphenylylcarbonyl)-propionic Acid

126. Ncgc00016834-02

127. Ncgc00016834-03

128. Ncgc00016834-04

129. Ncgc00016834-07

130. Ncgc00094886-01

131. Ncgc00094886-02

132. Ncgc00094886-03

133. Ac-14459

134. Sbi-0051631.p002

135. Ab00052195

136. Bb 0221124

137. Ft-0626394

138. Gamma-oxo(1,1''-biphenyl)-4-butanoic Acid

139. .gamma.-oxo(1,1'-biphenyl)-4-butanoic Acid

140. Diphenyl-4-.gamma.-oxo-.gamma.-butyric Acid

141. 4-([1,1'-biphenyl]-4-yl)-4-oxobutanoicacid

142. 4-[1,1''-biphenyl-4-yl]-4-oxobutanoic Acid

143. D01344

144. 4-[1,1'-biphenyl]-4-yl-4-oxobutanoic Acid #

145. Ab00052195-13

146. Ab00052195_14

147. Q2304195

148. Sr-01000721906-2

149. Sr-01000721906-4

150. Sr-01000721906-5

151. Brd-k12513978-001-05-0

152. Brd-k12513978-001-16-7

153. Z99599540

154. Fenbufen, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₄O₃
Molecular Weight	254.28 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	254.094294304 g/mol
Monoisotopic Mass	254.094294304 g/mol
Topological Polar Surface Area	54.4 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	310
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 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Cyclooxygenase Inhibitors

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

4.2 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AE - Propionic acid derivatives

M01AE05 - Fenbufen