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MolPort-002-070-322

MolPort-002-070-322

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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

MolPort-002-070-322

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 Formula	C₁₅H₁₂ClNO₂
Molecular Weight	273.71 g/mol
XLogP3	4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	273.0556563 g/mol
Monoisotopic Mass	273.0556563 g/mol
Topological Polar Surface Area	53.1 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	362
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
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 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.

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