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Diacerein

Synopsis, Chemistry

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Also known as: 13739-02-1, Diacerhein, Diacetylrhein, Artrodar, Fisiodar, 1,8-diacetoxy-3-carboxyanthraquinone

Molecular Formula

C₁₉H₁₂O₈

Molecular Weight

368.3 g/mol

InChI Key

TYNLGDBUJLVSMA-UHFFFAOYSA-N

FDA UNII

4HU6J11EL5

Diacerein is a prodrug which is metabolized to rhein. It is currently approved in France for the treatment of osteoarthritis although the use of diacerein is restricted due to the side effects including severe diarrhea. Diacerein is under investigation for the treatment of Insulin Resistance, Diabetes Mellitus (Type 2), and Diabetes-Related Complications.

1 2D Structure

Diacerein

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C19H12O8/c1-8(20)26-13-5-3-4-11-15(13)18(23)16-12(17(11)22)6-10(19(24)25)7-14(16)27-9(2)21/h3-7H,1-2H3,(H,24,25)

2.1.3 InChI Key

TYNLGDBUJLVSMA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(=O)OC1=CC=CC2=C1C(=O)C3=C(C2=O)C=C(C=C3OC(=O)C)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

4HU6J11EL5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1,8-diacetoxy-3-carboxyanthraquinone

2. 2-anthracenecarboxylic Acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-

3. 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic Acid

4. 4,5-diacetoxyanthraquinone-2-carboxylic Acid

5. 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic Acid, Diacetate

6. Ac-201

7. Ac-203

8. Artrodar

9. Diacerhein

10. Diacetyl-rhein

11. Diacetylrhein

12. Diora

13. Fisiodar

14. M-01ax21

15. M01ax21

16. Rhein Diacetate

17. Sf-277

18. Sf277

19. Verboril

20. Zondar

2.3.2 Depositor-Supplied Synonyms

1. 13739-02-1

2. Diacerhein

3. Diacetylrhein

4. Artrodar

5. Fisiodar

6. 1,8-diacetoxy-3-carboxyanthraquinone

7. Diacerin

8. Sf-277

9. Verboril

10. Zondar

11. Diora

12. 4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic Acid

13. M01ax21

14. Ac-201

15. 2-anthracenecarboxylic Acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-

16. 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic Acid

17. 4,5-diacetoxyanthraquinone-2-carboxylic Acid

18. M-01ax21

19. Diacerhein; Diacetylrhein

20. Mfcd00468030

21. Nsc-758147

22. Mls000028577

23. 4hu6j11el5

24. 4,5-diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic Acid

25. 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic Acid, Diacetate

26. 4,5-diacetylrhein

27. Ncgc00018274-04

28. Smr000058958

29. 4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic Acid

30. Dsstox_cid_25636

31. Dsstox_rid_81017

32. Diacerein [inn]

33. Dsstox_gsid_45636

34. Diacereine [french]

35. Diacereinum [latin]

36. Diacereina [spanish]

37. 4,5-diacetoxy-9,10-diketo-anthracene-2-carboxylic Acid

38. 4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic Acid

39. Diacereina

40. Diacereine

41. Diacereinum

42. Rhein Diacetate

43. Rhein, Diacetate

44. Cas-13739-02-1

45. Sr-01000003156

46. Einecs 237-310-2

47. Brn 2184909

48. Unii-4hu6j11el5

49. Gesamtmatrix

50. Art 50

51. 1,8-diacetoxyanthraquinone-3-carboxylic Acid

52. Diacerein- Bio-x

53. Zondar (tn)

54. Spectrum_001876

55. Specplus_000643

56. 4,5-diacetoxy-9,10-dihydro-9,10-dioxo-2-anthrylcarbonsaeure

57. 9,10-dihydro-4,5-diacetoxy-9,10-2-anthracenecarboxylic Acid

58. Diacerein [mi]

59. Diacerein (usan/inn)

60. Diacerein [usan:inn]

61. Diacerein [usan]

62. 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic Acid Diacetate

63. Spectrum2_000823

64. Spectrum3_000937

65. Spectrum4_001036

66. Spectrum5_001819

67. Diacerein Impurity Mixture

68. Diacerein [mart.]

69. Diacerein [who-dd]

70. Schembl25784

71. Kbiogr_001591

72. Kbioss_002400

73. Rhein Diacetate [mi]

74. 3-10-00-04790 (beilstein Handbook Reference)

75. Cid_26248

76. Chembl41286

77. Divk1c_006739

78. Spectrum1502010

79. Spbio_000745

80. 4,5-diacetoxy-9,10-dioxo-anthracene-2-carboxylic Acid

81. Diacerein [ep Monograph]

82. Diacerein, >=95% (hplc)

83. Dtxsid4045636

84. Bdbm32018

85. Chebi:94708

86. Gtpl10800

87. Kbio1_001683

88. Kbio2_002395

89. Kbio2_004963

90. Kbio2_007531

91. Kbio3_001974

92. Hms3652d06

93. Hms3714b20

94. Pharmakon1600-01502010

95. Bcp10834

96. Hy-n0283

97. Who 5371

98. Zinc3812842

99. Tox21_110856

100. Bbl011075

101. Ccg-40287

102. Nsc758147

103. S4267

104. Stk802271

105. 2-anthroic Acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, Diacetate

106. Akos005622705

107. Tox21_110856_1

108. Db11994

109. Ks-5088

110. Kw-4800

111. Nsc 758147

112. Ncgc00018274-01

113. Ncgc00018274-02

114. Ncgc00018274-03

115. Ncgc00018274-05

116. Ncgc00022114-03

117. Am807992

118. Bd164367

119. Sbi-0052833.p002

120. B1726

121. D4061

122. Ft-0603096

123. Sw199355-2

124. D07270

125. Ab00053327_14

126. 739d021

127. A807252

128. Q413178

129. Sr-01000003156-2

130. Sr-01000003156-3

131. Sr-01000003156-4

132. W-108237

133. Diacerein, European Pharmacopoeia (ep) Reference Standard

134. 4,5-diacetoxy-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic Acid

135. 4,5-diacetyloxy-9,10-bis(oxidanylidene)anthracene-2-carboxylic Acid

136. 4,5-bis(acetoxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic Acid

137. 112118-18-0

2.4 Create Date

2005-06-29

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₂O₈
Molecular Weight	368.3 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	368.05321734 g/mol
Monoisotopic Mass	368.05321734 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	683
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 Indication

For the treatment of osteoarthritis affecting the hip or knee.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Decreases inflammation and cartilage destruction and also corrects altered osteoblast acitivity.

5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

5.3 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AX - Other antiinflammatory and antirheumatic agents, non-steroids

M01AX21 - Diacerein

5.4 Absorption, Distribution and Excretion

Absorption

Bioavailability of 50-60%. Entirely converted to the active metabolite rhein [DB13174] before reaching systemic circulation.

Route of Elimination

37% excreted in urine and 53% in feces as estimated in rats.

Volume of Distribution

15-60L.

Clearance

Total CL is 1.5L/h and renal CL is 0.1L/h.

5.5 Metabolism/Metabolites

Entirely converted to rhien [DB13174] through double deacetylation before reaching systemic circulation. Rhein [DB13174] is further metabolized to rhein glucuronide and rhein sulfate.

5.6 Biological Half-Life

4-10h.

5.7 Mechanism of Action

Diacerein's active metabolite rhein [DB13174] reduces cartilage destruction by decreasing expression of matrix metalloproteinase (MMP)-1 and -3 as well as upregulating tissue inhibitor of matrix metalloproteinases which serve to reduce the activity of several MMPs. The anti-inflammatory action of rhein reduces the level of interleukin-1beta activity which plays a large role in reduction of extracellular matrix production, MMP activity, and continued inflammation. Rhein reduces abnormal osteoblast synthetic activity through an unknown mechanism.