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    Carprofen

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    2D Structure
    Also known as: 53716-49-7, 2-(6-chloro-9h-carbazol-2-yl)propanoic acid, Rimadyl, Imadyl, Ridamyl, Carprofeno
    Molecular Formula
    C15H12ClNO2
    Molecular Weight
    273.71  g/mol
    InChI Key
    PUXBGTOOZJQSKH-UHFFFAOYSA-N
    FDA UNII
    FFL0D546HO
    Carprofen is a propionic acid derivate and nonsteroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic, and antipyretic activities, used exclusively in veterinary medicine. Carprofen inhibits the activity of the enzymes cyclo-oxygenase (COX) I and II, resulting in a decreased formation of precursors of prostaglandins and thromboxanes. This inhibits the formation of prostaglandins, by prostaglandin synthase, that are involved in pain, inflammation and fever. Ibuprofen also causes a decrease in the formation of thromboxane A2 synthesis, by thromboxane synthase, thereby inhibiting platelet aggregation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-(6-chloro-9H-carbazol-2-yl)propanoic acid
    2.1.2 InChI
    InChI=1S/C15H12ClNO2/c1-8(15(18)19)9-2-4-11-12-7-10(16)3-5-13(12)17-14(11)6-9/h2-8,17H,1H3,(H,18,19)
    2.1.3 InChI Key
    PUXBGTOOZJQSKH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C1=CC2=C(C=C1)C3=C(N2)C=CC(=C3)Cl)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    FFL0D546HO
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (+-)-isomer Of Carprofen

    2. (r)-isomer Of Carprofen

    3. (s)-isomer Of Carprofen

    4. C 5720

    5. Carprofen, (+-)-isomer

    6. Carprofen, (r)-isomer

    7. Carprofen, (s)-isomer

    8. Ro 20-5720

    9. Ro 205720

    2.3.2 Depositor-Supplied Synonyms

    1. 53716-49-7

    2. 2-(6-chloro-9h-carbazol-2-yl)propanoic Acid

    3. Rimadyl

    4. Imadyl

    5. Ridamyl

    6. Carprofeno

    7. Carprofene

    8. Carprofenum

    9. Carprofene [inn-french]

    10. Carprofenum [inn-latin]

    11. 6-chloro-alpha-methyl-9h-carbazole-2-acetic Acid

    12. Carprofeno [inn-spanish]

    13. 6-chloro-alpha-methylcarbazole-2-acetic Acid

    14. Ro 20-5720/000

    15. Mfcd00079028

    16. Carprofen-d3

    17. (+-)-6-chloro-alpha-methylcarbazole-2-acetic Acid

    18. 52263-47-5

    19. 2-(6-chloro-9h-carbazol-2-yl)-propionic Acid

    20. Nsc-297935

    21. Carprofen For Veterinary Use

    22. Chembl1316

    23. Ffl0d546ho

    24. (+/-)-2-(3-chloro-9h-carbazol-7-yl)propanoic Acid

    25. Ro-20-5720/000

    26. Chebi:364453

    27. Nsc297935

    28. 9h-carbazole-2-acetic Acid, 6-chloro-.alpha.-methyl-

    29. Ncgc00094937-01

    30. Carprodyl

    31. Carprofeno [spanish]

    32. Ro-205720000

    33. Dsstox_cid_25871

    34. Dsstox_rid_81189

    35. Dsstox_gsid_45871

    36. (.+-.)-6-chloro-.alpha.-methylcarbazole-2-acetic Acid

    37. Carpaquin

    38. Norocarp

    39. Ro 20-5720

    40. Smr000718633

    41. Rimadyl (tn)

    42. C 5720

    43. Cas-53716-49-7

    44. Ccris 3507

    45. Sr-01000837515

    46. Einecs 258-712-4

    47. Unii-ffl0d546ho

    48. Nsc 297935

    49. Brn 0487098

    50. Rac Carprofen

    51. Carprofen [usan:usp:inn:ban]

    52. Ro-20-5720

    53. Carprofen (usp/inn)

    54. Carprofen [inn]

    55. Carprofen [mi]

    56. Carprofen [usan]

    57. Spectrum2_001236

    58. Spectrum3_000939

    59. Spectrum4_001038

    60. Spectrum5_001802

    61. Carprofen [vandf]

    62. Carprofen [mart.]

    63. C-5720

    64. Carprofen [usp-rs]

    65. Carprofen [who-dd]

    66. Schembl3909

    67. (+-)-6-chlor-alpha-methyl-2-carbazolessigsaeure

    68. Kbiogr_001595

    69. 5-22-03-00391 (beilstein Handbook Reference)

    70. Mls001201778

    71. Mls001306441

    72. Spectrum1502006

    73. Spbio_001112

    74. Carprofen [green Book]

    75. Gtpl7141

    76. Carprofen [orange Book]

    77. (+/-)-6-chloro-.alpha.-methylcarbazole-2-acetic Acid

    78. Carprofen [usp Impurity]

    79. Carprofen, >=97% (hplc)

    80. Dtxsid1045871

    81. Kbio3_001978

    82. Carprofen [usp Monograph]

    83. Hms1921d04

    84. Hms2092b16

    85. Hms2234p15

    86. Hms3652e20

    87. Hms3715f09

    88. Hms3748c07

    89. Hms3885f07

    90. Pharmakon1600-01502006

    91. Act03356

    92. Hy-b1227

    93. Tox21_111363

    94. 9h-carbazole-2-acetic Acid, 6-chloro-.alpha.-methyl-, (.+-.)-

    95. 9h-carbazole-2-acetic Acid, 6-chloro-alpha-methyl-, (+-)-

    96. Bbl009935

    97. Bdbm50097346

    98. Ccg-39146

    99. Nsc758154

    100. Stk711093

    101. 9h-carbazole-2-acetic Acid, (-)-

    102. Akos005530663

    103. Tox21_111363_1

    104. Ac-1266

    105. Cs-4875

    106. Db00821

    107. Ks-1163

    108. Nsc-758154

    109. Carprofen 100 Microg/ml In Acetonitrile

    110. Ncgc00094937-02

    111. Ncgc00094937-04

    112. Ncgc00094937-05

    113. 9h-carbazole-2-acetic Acid, (.+-.)-

    114. Sbi-0052885.p002

    115. Ft-0602833

    116. Ft-0664393

    117. Ft-0664394

    118. Ft-0664395

    119. S4136

    120. Sw199610-3

    121. 6-chloro-alpha-methyl-carbazole-2-acetic Acid

    122. Carprofen, Vetranal(tm), Analytical Standard

    123. C18364

    124. D03410

    125. D70911

    126. 2-(6-chloranyl-9h-carbazol-2-yl)propanoic Acid

    127. Ab00876263_06

    128. Ab00876263_07

    129. 716c497

    130. A829748

    131. Q905755

    132. (+/-)-6-chloro-alpha-methylcarbazole-2-aceticacid

    133. Carprofen For Veterinary Use [ep Monograph]

    134. Sr-01000837515-2

    135. Sr-01000837515-3

    136. (+/-)-6-chloro-alpha-methylcarbazole-2-acetic Acid

    137. Brd-a17411484-001-05-1

    138. Z1814381791

    139. 2-(6-chloro-9h-carbazol-2-yl)-propionic Acid(carprofen)

    140. Carprofen, European Pharmacopoeia (ep) Reference Standard

    141. 9h-carbazole-2-acetic Acid, 6-chloro-.alpha.-methyl-, (-)-

    142. Carprofen, United States Pharmacopeia (usp) Reference Standard

    143. 9h-carbazole-2-acetic Acid, 6-chloro-.alpha.-methyl, (+/-)-

    144. Carprofen, Pharmaceutical Secondary Standard; Certified Reference Material

    145. Carprofen For System Suitability, European Pharmacopoeia (ep) Reference Standard

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 273.71 g/mol
    Molecular Formula C15H12ClNO2
    XLogP34
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count2
    Exact Mass273.0556563 g/mol
    Monoisotopic Mass273.0556563 g/mol
    Topological Polar Surface Area53.1 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity362
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For use as a pain reliever in the treatment of joint pain and post-surgical pain.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Carprofen is a non-steroidal anti-inflammatory drug (NSAID) of the propionic acid class that includes ibuprofen, naproxen, and ketoprofen. It is no longer used in the clinical setting, but is approved for use in dogs. Carprofen is non-narcotic and has characteristic analgesic and antipyretic activity approximately equipotent to indomethacin in animal models.

    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.)

    Photosensitizing Agents

    Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. (See all compounds classified as Photosensitizing Agents.)

    5.3 Absorption, Distribution and Excretion

    Absorption

    Rapidly and nearly completely absorbed (more than 90% bioavailable) when administered orally.

    5.4 Metabolism/Metabolites

    Hepatic.

    5.5 Biological Half-Life

    Approximately 8 hours (range 4.5–9.8 hours) in dogs.

    5.6 Mechanism of Action

    The mechanism of action of carprofen, like that of other NSAIDs, is believed to be associated with the inhibition of cyclooxygenase activity. Two unique cyclooxygenases have been described in mammals. The constitutive cyclooxygenase, COX-1, synthesizes prostaglandins necessary for normal gastrointestinal and renal function. The inducible cyclooxygenase, COX-2, generates prostaglandins involved in inflammation. Inhibition of COX-1 is thought to be associated with gastrointestinal and renal toxicity while inhibition of COX-2 provides anti-inflammatory activity. In an in vitro study using canine cell cultures, carprofen demonstrated selective inhibition of COX-2 versus COX-1.