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    Salsalate

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 552-94-3, Sasapyrine, Salicylsalicylic acid, Disalicylic acid, Disalcid, 2-carboxyphenyl salicylate
    Molecular Formula
    C14H10O5
    Molecular Weight
    258.23  g/mol
    InChI Key
    WVYADZUPLLSGPU-UHFFFAOYSA-N
    FDA UNII
    V9MO595C9I
    Salsalate is an orally available salicylate and non-steroidal anti-inflammatory drug (NSAID), with anti-inflammatory, analgesic and antipyretic activities. As a prodrug, salsalate is hydrolyzed to salicylic acid which inhibits the expression of cyclooxygenase (COX) enzymes. This prevents the conversion of arachidonic acid into prostaglandin precursors and leads to decreased formation of prostaglandins that are involved in pain, fever and inflammation. In addition, salsalate appears to inhibit nuclear factor-kappa B (NF-kB), thereby preventing activation of the NF-kB-mediated pathway and the expression of genes involved in inflammation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-(2-hydroxybenzoyl)oxybenzoic acid
    2.1.2 InChI
    InChI=1S/C14H10O5/c15-11-7-3-1-5-9(11)14(18)19-12-8-4-2-6-10(12)13(16)17/h1-8,15H,(H,16,17)
    2.1.3 InChI Key
    WVYADZUPLLSGPU-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C(C(=C1)C(=O)OC2=CC=CC=C2C(=O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    V9MO595C9I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Arcylate

    2. Argesic

    3. Benzoic Acid, 2-hydroxy-, 2-carboxyphenyl Ester

    4. Disalcid

    5. Disalicylic Acid

    6. Mono-gesic

    7. Salflex

    8. Salicyl Salicylate

    9. Salicylsalicylic Acid

    10. Saloxium

    11. Salsitab

    2.3.2 Depositor-Supplied Synonyms

    1. 552-94-3

    2. Sasapyrine

    3. Salicylsalicylic Acid

    4. Disalicylic Acid

    5. Disalcid

    6. 2-carboxyphenyl Salicylate

    7. Sasapyrinum

    8. Saloxium

    9. Salicyloylsalicylic Acid

    10. Diacesal

    11. Diplosal

    12. Sasapirin

    13. Sasapyrin

    14. Disalyl

    15. Nobacid

    16. Salical

    17. Salina

    18. Salysal

    19. O-salicylsalicylic Acid

    20. Sal Ester Sal

    21. 2-(2-hydroxybenzoyl)oxybenzoic Acid

    22. Disalicylsaeure

    23. Benzoic Acid, 2-hydroxy-, 2-carboxyphenyl Ester

    24. Salicylic Acid, Salicylate

    25. Nsc-49171

    26. Salicylic Acid, Bimolecular Ester

    27. Salsalato

    28. Salsalatum

    29. Salflex

    30. Salsalatum [inn-latin]

    31. 2-((2-hydroxybenzoyl)oxy)benzoic Acid

    32. Salicyloxysalicylic Acid

    33. O-salicylcylsalicylsaeure

    34. Disalicyclic Acid

    35. Sasapyrine (jan)

    36. 2-hydroxybenzoic Acid 2-carboxyphenyl Ester

    37. Salicylsalicylic Acid;disalicylic Acid

    38. Chebi:9014

    39. V9mo595c9i

    40. Salicylic Acid Bimolecular Ester

    41. Nsc49171

    42. Ncgc00096014-01

    43. Sasapyrine [jan]

    44. Dsstox_cid_3572

    45. Dsstox_rid_77088

    46. Dsstox_gsid_23572

    47. Salsalato [inn-spanish]

    48. 2-[(2-hydroxybenzoyl)oxy]benzoic Acid (salicylsalicylic Acid)

    49. Mono-gesic

    50. O-salicyloylsalicylic Acid

    51. Disalcid (tn)

    52. Cas-552-94-3

    53. Salsalate (usp/inn)

    54. Einecs 209-027-4

    55. Mfcd00020252

    56. Nsc 49171

    57. 2-salicyloyloxybenzoic Acid

    58. Brn 2590908

    59. Unii-v9mo595c9i

    60. Disalgesic

    61. Salicylsalicylic Acid (2-[(2-hydroxybenzoyl)oxy]benzoic Acid)

    62. Salsalate [usan:usp:inn:ban]

    63. Aspirin Impurity E

    64. 2-(2-hydroxybenzoyloxy)benzoic Acid

    65. Carboxyphenyl Salicylate

    66. Spectrum_001998

    67. 2-salicylsalicylic Acid

    68. Salsalate [inn]

    69. Salsalate [mi]

    70. Salsalate [usan]

    71. Spectrum2_000693

    72. Spectrum3_000173

    73. Spectrum4_000940

    74. Spectrum5_000670

    75. Salsalate [vandf]

    76. Salsalate [mart.]

    77. Salsalate [usp-rs]

    78. Salsalate [who-dd]

    79. 2-{[(2-hydroxyphenyl)carbonyl]oxy}benzoic Acid

    80. 2-salicyloyloxy-benzoic Acid

    81. Schembl15562

    82. Bspbio_001665

    83. Kbiogr_001500

    84. Kbioss_002572

    85. Spectrum200331

    86. Spbio_000845

    87. Acetylsalicylic Acid Impurity E

    88. Chembl154111

    89. Zinc2062

    90. Dtxsid1023572

    91. Salsalate [usp Impurity]

    92. Salsalate, >=98% (hplc)

    93. Bdbm85244

    94. Kbio2_002563

    95. Kbio2_005131

    96. Kbio2_007699

    97. Kbio3_001165

    98. Salsalate [usp Monograph]

    99. Hms2091a05

    100. Hms3652p07

    101. Hms3885j09

    102. Pharmakon1600-00200331

    103. Hy-b1245

    104. Nsc_5161

    105. Benzoic Acid, 2-carboxyphenyl Ester

    106. Tox21_111548

    107. Ccg-39652

    108. Nsc755823

    109. S4188

    110. Salicylic Acid 2-carboxyphenyl Ester

    111. Akos003368478

    112. Tox21_111548_1

    113. 2-carboxyphenyl Salicylate, Aldrichcpr

    114. Cs-4891

    115. Db01399

    116. Nsc-755823

    117. Ncgc00096014-02

    118. Ncgc00096014-03

    119. Ac-18298

    120. As-12645

    121. Cas_552-94-3

    122. 2-[(2-hydroxybenzoyl)oxy]benzoic Acid #

    123. Sbi-0206687.p002

    124. Db-020760

    125. Ft-0632376

    126. Sw219189-1

    127. 2-[(2-hydroxyphenyl)carbonyloxy]benzoic Acid

    128. C75590

    129. D00428

    130. Ab01563259_01

    131. Ab01563259_02

    132. A830578

    133. Sr-05000001536

    134. Q-100630

    135. Q1320691

    136. Sr-05000001536-1

    137. Acetylsalicylic Acid Impurity E [ep Impurity]

    138. Salsalate, United States Pharmacopeia (usp) Reference Standard

    139. Aspirin Impurity E; 2-hydroxybenzoic Acid 2-carboxyphenyl Ester; Salicylic Acid Salicylate; 2-hydroxybenzoic Acid 2-carboxyphenyl Ester

    140. Salsalate (aspirin Impurity E), Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 258.23 g/mol
    Molecular Formula C14H10O5
    XLogP33
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass258.05282342 g/mol
    Monoisotopic Mass258.05282342 g/mol
    Topological Polar Surface Area83.8 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity341
    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 relief of the signs and symptoms of rheumatoid arthritis, osteoarthritis and related rheumatic disorders.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Salsalate is a nonsteroidal anti-inflammatory agent for oral administration. Salsalate's mode of action as an anti-inflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. The usefulness of salicylic acid, the active in vivo product of salsalate, in the treatment of arthritic disorders has been established. In contrast to aspirin, salsalate causes no greater fecal gastrointestinal blood loss than placebo.

    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.)

    5.3 ATC Code

    N - Nervous system

    N02 - Analgesics

    N02B - Other analgesics and antipyretics

    N02BA - Salicylic acid and derivatives

    N02BA06 - Salsalate

    5.4 Absorption, Distribution and Excretion

    Absorption

    Salsalate is insoluble in acid gastric fluids (< 0.1 mg/ml at pH 1.0), but readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged. The amount of salicylic acid available from salsalate is about 15% less than from aspirin, when the two drugs are administered on a salicylic acid molar equivalent basis (3.6 g salsalate/5 g aspirin). Food slows the absorption of all salicylates including salsalate.

    5.5 Metabolism/Metabolites

    Salsalate is readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged and undergoes rapid esterase hydrolysis in the body.

    5.6 Biological Half-Life

    The parent compound has an elimination half-life of about 1 hour. Salicylic acid (the active metabolite) biotransformation is saturated at anti-inflammatory doses of salsalate. Such capacity limited biotransformation results in an increase in the half-life of salicylic acid from 3.5 to 16 or more hours.

    5.7 Mechanism of Action

    The mode of anti-inflammatory action of salsalate and other nonsteroidal anti-inflammatory drugs is not fully defined, but appears to be primarily associated with inhibition of prostaglandin synthesis. This inhibition of prostaglandin synthesis is done through the inactivation of cyclooxygenase-1 (COX-1) and COX-2, which are reponsible for catalyzing the formation of prostaglandins in the arachidonic acid pathway. Although salicylic acid (the primary metabolite of salsalate) is a weak inhibitor of prostaglandin synthesis in vitro, salsalate appears to selectively inhibit prostaglandin synthesis in vivo, providing anti-inflammatory activity equivalent to aspirin and indomethacin. Unlike aspirin, salsalate does not inhibit platelet aggregation.