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Chemistry

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Also known as: 22494-42-4, Dolobid, Dolobis, Fluniget, Flovacil, Fluodonil
Molecular Formula
C13H8F2O3
Molecular Weight
250.20  g/mol
InChI Key
HUPFGZXOMWLGNK-UHFFFAOYSA-N
FDA UNII
7C546U4DEN

Diflunisal
A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN.
Diflunisal is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of diflunisal is as a Cyclooxygenase Inhibitor.
1 2D Structure

Diflunisal

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-(2,4-difluorophenyl)-2-hydroxybenzoic acid
2.1.2 InChI
InChI=1S/C13H8F2O3/c14-8-2-3-9(11(15)6-8)7-1-4-12(16)10(5-7)13(17)18/h1-6,16H,(H,17,18)
2.1.3 InChI Key
HUPFGZXOMWLGNK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1C2=C(C=C(C=C2)F)F)C(=O)O)O
2.2 Other Identifiers
2.2.1 UNII
7C546U4DEN
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Apo Diflunisal

2. Apo-diflunisal

3. Apodiflunisal

4. Dolobid

5. Dolobis

6. Dolocid

7. Mk 647

8. Mk-647

9. Mk647

10. Novo Diflunisal

11. Novo-diflunisal

12. Novodiflunisal

13. Nu Diflunisal

14. Nu-diflunisal

15. Nudiflunisal

2.3.2 Depositor-Supplied Synonyms

1. 22494-42-4

2. Dolobid

3. Dolobis

4. Fluniget

5. Flovacil

6. Fluodonil

7. Adomal

8. Flustar

9. 5-(2,4-difluorophenyl)salicylic Acid

10. Mk-647

11. 5-(2,4-difluorophenyl)-2-hydroxybenzoic Acid

12. Diflusinal

13. Mk 647

14. 5-[2,4-difluorophenyl]salicylic Acid

15. 2',4'-difluoro-4-hydroxy-3-biphenylcarboxylic Acid

16. 2-(hydroxy)-5-(2,4-difluorophenyl)benzoic Acid

17. [1,1'-biphenyl]-3-carboxylic Acid, 2',4'-difluoro-4-hydroxy-

18. 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic Acid

19. 5-(2,4-difluorophenyl)-2-hydroxy-benzoic Acid

20. 2',4'-difluoro-4-hydroxy[1,1'-biphenyl]-3-carboxylic Acid

21. 2',4'-difluoro-4-hydroxy-(1,1'-biphenyl)-3-carboxylic Acid

22. Chembl898

23. Nsc-756728

24. (1,1'-biphenyl)-3-carboxylic Acid, 2',4'-difluoro-4-hydroxy-

25. Mls000028678

26. 7c546u4den

27. Algobid

28. Citidol

29. Difludol

30. Noaldol

31. Reuflos

32. 2',4'-difluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxylic Acid

33. 3-biphenylcarboxylic Acid, 2',4'-difluoro-4-hydroxy-

34. Chebi:39669

35. Unisal

36. 2',4'-difluoro-4-hydroxy-biphenyl-3-carboxylic Acid

37. Ncgc00016765-01

38. Diflunisalum

39. Dolisal

40. Dolobil

41. Smr000058723

42. Cas-22494-42-4

43. Dsstox_cid_2932

44. Dsstox_rid_76792

45. Dsstox_gsid_22932

46. Diflunisalum [inn-latin]

47. 1fl

48. Dolobid (tn)

49. Mk647

50. Sr-01000003165

51. Einecs 245-034-9

52. Mfcd00057834

53. Brn 2654431

54. Unii-7c546u4den

55. Diflunisal (jan/usp/inn)

56. Prestwick_168

57. Diflunisal [usan:usp:inn:ban:jan]

58. Spectrum_000962

59. Diflunisal [mi]

60. Opera_id_803

61. Diflunisal [inn]

62. Diflunisal [jan]

63. Prestwick0_000039

64. Prestwick1_000039

65. Prestwick2_000039

66. Prestwick3_000039

67. Spectrum2_001012

68. Spectrum3_000392

69. Spectrum4_000513

70. Spectrum5_000901

71. Diflunisal [usan]

72. Diflunisal [vandf]

73. Diflunisal [mart.]

74. Schembl4337

75. Diflunisal [usp-rs]

76. Diflunisal [who-dd]

77. Bspbio_000137

78. Bspbio_002203

79. Kbiogr_001085

80. Kbioss_001442

81. Mls001146895

82. Bidd:gt0063

83. Divk1c_000938

84. Spectrum1500245

85. Spbio_001163

86. Spbio_002058

87. Diflunisal, Analytical Standard

88. Bpbio1_000151

89. Gtpl7162

90. Diflunisal [ep Impurity]

91. Diflunisal [orange Book]

92. Dtxsid5022932

93. Hms502o20

94. Kbio1_000938

95. Kbio2_001442

96. Kbio2_004010

97. Kbio2_006578

98. Kbio3_001423

99. Zinc20243

100. Diflunisal [usp Impurity]

101. Ninds_000938

102. Diflunisal [usp Monograph]

103. Hms1568g19

104. Hms1920g10

105. Hms2090c16

106. Hms2091m20

107. Hms2095g19

108. Hms3259g17

109. Hms3712g19

110. Hms3885h10

111. Pharmakon1600-01500245

112. Bcp09905

113. Tox21_110598

114. Bdbm50240510

115. Ccg-40230

116. Nsc756728

117. S4609

118. Akos005762917

119. Tox21_110598_1

120. Db00861

121. Ks-1346

122. Nc00506

123. Nsc 756728

124. Idi1_000938

125. Ncgc00016765-02

126. Ncgc00016765-03

127. Ncgc00016765-04

128. Ncgc00016765-05

129. Ncgc00016765-06

130. Ncgc00016765-08

131. Ncgc00016765-09

132. Ncgc00022783-03

133. Ncgc00022783-04

134. 1286107-99-0

135. Diflunisal 100 Microg/ml In Acetonitrile

136. Hy-18342

137. Sbi-0051347.p003

138. Db-045934

139. Ab00051969

140. Cs-0007468

141. D5875

142. Ft-0630487

143. C01691

144. D00130

145. Ab00051969-12

146. Ab00051969_13

147. A816230

148. 2',4'-difluoro-4-hydroxybipheny-3-carboxylic Acid

149. J-014739

150. Q2602750

151. Sr-01000003165-2

152. Sr-01000003165-3

153. Brd-k22031190-001-05-3

154. Brd-k22031190-001-13-7

155. 5-(2,4-difluorophenyl)-2-hydroxy-benzoic Acid;diflunisal

156. Diflunisal, European Pharmacopoeia (ep) Reference Standard

157. 2',4'-difluoro-4-hydroxy-(1',1-diphenyl)-3-carboxylic Acid

158. Diflunisal, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 250.20 g/mol
Molecular Formula C13H8F2O3
XLogP34.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass250.04415044 g/mol
Monoisotopic Mass250.04415044 g/mol
Topological Polar Surface Area57.5 Ų
Heavy Atom Count18
Formal Charge0
Complexity311
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 NameDiflunisal
PubMed HealthDiflunisal (By mouth)
Drug ClassesAnalgesic, Antirheumatic
Drug LabelDiflunisal is [1, 1-Biphenyl]-3-carboxylic acid, 2, 4-difluoro-4-hydroxy. Its structural formula is:Molecular Formula: C13H8F2O3Molecular Weight: 250.20 g/molDiflunisal is a stable, white, crystalline compound with a melting point of 211...
Active IngredientDiflunisal
Dosage FormTablet
RouteOral
Strength500mg
Market StatusPrescription
CompanyTeva; Emcure Pharms Usa

2 of 2  
Drug NameDiflunisal
PubMed HealthDiflunisal (By mouth)
Drug ClassesAnalgesic, Antirheumatic
Drug LabelDiflunisal is [1, 1-Biphenyl]-3-carboxylic acid, 2, 4-difluoro-4-hydroxy. Its structural formula is:Molecular Formula: C13H8F2O3Molecular Weight: 250.20 g/molDiflunisal is a stable, white, crystalline compound with a melting point of 211...
Active IngredientDiflunisal
Dosage FormTablet
RouteOral
Strength500mg
Market StatusPrescription
CompanyTeva; Emcure Pharms Usa

4.2 Drug Indication

For symptomatic treatment of mild to moderate pain accompanied by inflammation (e.g. musculoskeletal trauma, post-dental extraction, post-episiotomy), osteoarthritis, and rheumatoid arthritis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Diflunisal is a nonsteroidal drug with analgesic, anti-inflammatory and antipyretic properties. It is a peripherally-acting non-narcotic analgesic drug. Habituation, tolerance and addiction have not been reported. Diflunisal is a difluorophenyl derivative of salicylic acid. Chemically, diflunisal differs from aspirin (acetylsalicylic acid) in two respects. The first of these two is the presence of a difluorophenyl substituent at carbon 1. The second difference is the removal of the 0-acetyl group from the carbon 4 position. Diflunisal is not metabolized to salicylic acid, and the fluorine atoms are not displaced from the difluorophenyl ring structure.


5.2 MeSH Pharmacological Classification

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.)


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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DIFLUNISAL
5.3.2 FDA UNII
7C546U4DEN
5.3.3 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
5.4 ATC Code

N - Nervous system

N02 - Analgesics

N02B - Other analgesics and antipyretics

N02BA - Salicylic acid and derivatives

N02BA11 - Diflunisal


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly and completely absorbed following oral administration, with a bioavailability of 80-90%. Peak plasma concentrations are achieved 2 - 3 hours following oral administration.


Route of Elimination

The drug is excreted in the urine as two soluble glucuronide conjugates accounting for about 90% of the administered dose. Little or no diflunisal is excreted in the feces.


5.6 Metabolism/Metabolites

Hepatic, primarily via glucuronide conjugation (90% of administered dose).


5.7 Biological Half-Life

8 to 12 hours


5.8 Mechanism of Action

The precise mechanism of the analgesic and anti-inflammatory actions of diflunisal is not known. Diflunisal is a prostaglandin synthetase inhibitor. In animals, prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain. Since prostaglandins are known to be among the mediators of pain and inflammation, the mode of action of diflunisal may be due to a decrease of prostaglandins in peripheral tissues.


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28-Jan-2021
12-Sep-2024
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