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    Diacerein

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    GLOBAL SALES INFORMATION

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

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    2D Structure
    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

    2D Structure

    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 Weight 368.3 g/mol
    Molecular Formula C19H12O8
    XLogP31.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count5
    Exact Mass368.05321734 g/mol
    Monoisotopic Mass368.05321734 g/mol
    Topological Polar Surface Area124 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity683
    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 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.