Anti-arthritic agents: Progress and potential

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 13, 2015, Pages 3059-3080

  Laev, Sergey S ^a   Salakhutdinov, Nariman F ^a,b  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

Author keywords

Cyclooxygenase; Disease modifying anti rheumatic drugs; Kinase; Methotrexate; Natural products; Non steroidal anti inflammatory drugs; Nutraceuticals; Osteoarthritis; Rheumatoid arthritis

Indexed keywords

ACETYLSALICYLIC ACID; ANTIRHEUMATIC AGENT; CELECOXIB; CODEINE; CYCLOOXYGENASE 3; DICLOFENAC; DISEASE MODIFYING ANTIRHEUMATIC DRUG; GLUCOCORTICOID; GLUCOCORTICOID RECEPTOR; IBUPROFEN; INDOLEACETIC ACID DERIVATIVE; INDOMETACIN; INDUCIBLE NITRIC OXIDE SYNTHASE; MISOPROSTOL; NAPROXEN; NATURAL PRODUCT; NONSTEROID ANTIINFLAMMATORY AGENT; NUTRACEUTICAL; OPIATE DERIVATIVE; PARACETAMOL; PHENYLBUTAZONE; PIROXICAM; PREDNISOLONE; PREDNISONE; ROFECOXIB; SALICYLIC ACID DERIVATIVE; TRAMADOL; TRANSCRIPTION FACTOR; UNINDEXED DRUG; VALDECOXIB; BIOLOGICAL PRODUCT; METHOTREXATE; NARCOTIC ANALGESIC AGENT; NEW DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; BINDING AFFINITY; DRUG BINDING SITE; DRUG EFFICACY; DRUG QUALITY; DRUG RECEPTOR BINDING; DRUG RESEARCH; DRUG STRUCTURE; DRUG TARGETING; ENZYME INHIBITION; FEVER; FRACTURE; GASTROINTESTINAL HEMORRHAGE; GASTROINTESTINAL SYMPTOM; GASTROINTESTINAL TOXICITY; GOUT; HUMAN; INFLAMMATORY DISEASE; INTRACTABLE PAIN; KNEE OSTEOARTHRITIS; KNEE PAIN; META ANALYSIS (TOPIC); OSTEOARTHRITIS; OSTEOPOROSIS; PAIN; POSTOPERATIVE PAIN; PROTEIN SYNTHESIS INHIBITION; PSORIATIC ARTHRITIS; RANDOMIZED CONTROLLED TRIAL (TOPIC); RHEUMATIC DISEASE; RHEUMATOID ARTHRITIS; STOMACH DISEASE; STOMACH ULCER; STRUCTURE ANALYSIS; ULCER; UNSPECIFIED SIDE EFFECT; ARTHRITIS, RHEUMATOID; CARTILAGE; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; JOINT; PATHOLOGY; PATHOPHYSIOLOGY; SYNTHESIS;

ANALGESICS, OPIOID; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTIRHEUMATIC AGENTS; ARTHRITIS, RHEUMATOID; BIOLOGICAL PRODUCTS; CARTILAGE; DRUGS, INVESTIGATIONAL; GLUCOCORTICOIDS; HUMANS; JOINTS; METHOTREXATE; OSTEOARTHRITIS; PAIN;

EID: 84937390660     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.05.010     Document Type: Article

References (221)

1. Y. Henrotin, C. Lambert, D. Couchourel, C. Ripoll, and E. Chiotelli Osteoarthr. Cartilage 19 2011 1
2. M.B. Goldring, and K.B. Marcu Arthritis Res. Ther. 11 2009 224
3. S.L. Dunn, J.M. Wilkinson, A. Crawford, C.L. Le Maintre, and R.A.D. Bunning Future Med. Chem. 4 2012 713
4. C. Buhrmann, A. Mobasheri, U. Matis, and M. Shakibaei Arthritis Res. Ther. 12 2010 R127
5. R.M. Pope Nat. Rev. Immunol. 2 2002 527
6. S. Ahmed Arthritis Res. Ther. 12 2010 208
7. C.J. Malemud Future Med. Chem. 4 2012 701
8. A.D. Beaulieu, P.M. Peloso, B. Haraoui, W. Bensen, G. Thomson, J. Wade, P. Quigley, J. Eisenhoffer, Z. Harsanyi, and A.C. Darke Pain Res. Manag. 13 2008 103
9. D.S. Cheng, and C.J. Visco PM R 4 2012 S82
10. C. Bachmeier, P.M. Brooks, R.O. Day, G.G. Graham, G.O. Littlejohn, E.F. Morand, K.D. Pile, and K.M. Williams F.P. Nijkamp, M.J. Parnham, Principles of Immunopharmacology 2nd ed. 2005 Birkhäuser Verlag Basel 511 544
11. P.J. Barnes Clin. Sci. 94 1998 557
12. P.N. Sambrook, and G. Jones Br. J. Rheumatol. 34 1995 8
13. R. Björkman Acta Anaesthesiol. Scand. Suppl. 103 1995 1
14. N.V. Chandrasekharan, H. Dai, K.L.T. Roos, N.K. Evanson, J. Tomsik, T.S. Elton, and D.L. Simmons Proc. Natl. Acad. Sci. U.S.A. 99 2002 13926
15. R. Botting, and S.S. Ayoub Prostaglandins Leukot. Essent. Fatty Acids 72 2005 85
16. J.-P. Courade, D. Besse, C. Delchambre, N. Hanoun, M. Hamon, A. Eschalier, F. Caussade, and A. Cloarec Life Sci. 69 2001 1455
17. W. Zhang, A. Jones, and M. Doherty Ann. Rheum. Dis. 63 2004 901
18. L.C. Hawkins, J.N. Edwards, and P.I. Dargan Drug Saf. 30 2007 465
19. R.G. Kulkarni, G. Achaiah, and G.N. Sastry Curr. Pharm. Des. 12 2006 2437
20. J.D. Bradley, K.D. Brandt, B.P. Katz, L.A. Kalasinski, and S.I.N. Ryan Engl. J. Med. 325 1991 87
21. T. Pincus, G. Koch, T. Sokka, J. Lefkowith, F. Wolfe, J.M. Jordan, G. Luta, L.F. Callahan, X. Wang, T. Schwartz, S.B. Abramson, J.R. Caldwell, R.A. Harrell, J.M. Kremer, R.L. Lautzenheiser, J.A. Markenson, T.J. Schnitzer, A. Weaver, P. Cummins, A. Wilson, S. Morant, and J. Fort Arthritis Rheum. 44 2001 1587
22. M. Weintraub, R.F. Jacox, C.D. Angevine, and E.C. Atwater J. Rheumatol. 4 1977 393
23. M.R. Griffin, J.M. Piper, J.R. Daugherty, M. Snowden, and W.A. Ray Ann. Intern. Med. 114 1991 257
24. E.C. Huskisson, H. Berry, P. Gishen, R.W. Jubb, and J. Whitehead J. Rheumatol. 22 1995 1941
25. W.G. Bensen, J.J. Fiechtner, J.I. McMillen, W.W. Zhao, S.S. Yu, E.M. Woods, R.C. Hubbard, P.C. Isakson, K.M. Verburg, and G.S. Geis Mayo Clin. Proc. 74 1999 1095
26. M.L. Chavez, and C.J. DeKorte Clin. Ther. 25 2003 817
27. F.M.P. Meier, M. Frerix, W. Hermann, and U. Müller-Ladner Immunotherapy 5 2013 955
28. K. Visser, and D. van der Heijde Ann. Rheum. Dis. 68 2009 1094
29. J.A.M. Wessels, T.W.J. Huizinga, and H.-J. Guchelaar Rheumatology 47 2008 249
30. C. Gaujoux-Viala, J.S. Smolen, R. Landewé, M. Dougados, T.K. Kvien, E.M. Mola, M. Scholte-Voshaar, P. van Riel, and L. Gossec Ann. Rheum. Dis. 69 2010 1004
31. H. Matsuoka, N. Maruyama, H. Suzuki, T. Kuroki, K. Tsuji, N. Kato, N. Ohi, M. Mihara, Y. Takeda, and K. Yano Chem. Pharm. Bull. 44 1996 2287
32. H. Matsuoka, N. Ohi, M. Mihara, H. Suzuki, K. Miyamoto, N. Maruyama, K. Tsuji, N. Kato, T. Akimoto, Y. Takeda, K. Yano, and T. Kuroki J. Med. Chem. 40 1997 105
33. M.C. Montesinos, A. Desai, D. Delano, J.-F. Chen, J.S. Fink, M.A. Jacobson, and B.N. Cronstein Arthritis Rheum. 48 2003 240
34. J.I. DeGraw, W.T. Colwell, J. Crase, R.L. Smith, J.R. Piper, W.R. Waud, and F.M. Sirotnak J. Med. Chem. 40 1997 370
35. E. Taherian, A. Rao, C.J. Malemud, and A.D. Askari Curr. Rheumatol. Rev. 9 2013 45
36. N.J. Olsen, M.A. Schleich, and D.R. Karp Semin. Arthritis Rheum. 43 2013 264
37. J.R. O'Dell, R. Leff, G. Paulsen, C. Haire, J. Mallek, P.J. Eckhoff, A. Fernandez, K. Blakely, S. Wees, J. Stoner, S. Hadley, J. Felt, W. Palmer, P. Waytz, M. Churchill, L. Klassen, and G. Moore Arthritis Rheum. 46 2002 1164
38. C.-H. Jang, J.-H. Choi, M.-S. Byun, and D.-M. Jue Rheumatology 45 2006 703
39. J.P. Davis, G.A. Cain, W.J. Pitts, R.L. Magolda, and R.A. Copeland Biochemistry 35 1996 1270
40. P. Maddison, P. Kiely, B. Kirkham, T. Lawson, R. Moots, D. Proudfoot, R. Reece, D. Scott, R. Sword, A. Taggart, C. Thwaites, and E. Williams Rheumatology 44 2005 280
41. M. Osiri, B. Shea, V. Robinson, M. Suarez-Almazor, V. Strand, P. Tugwell, and G. Wells J. Rheumatol. 30 2003 1182
42. F. Imai, T. Suzuki, T. Ishibashi, M. Tanaka, Y. Akiyama, and Y. Dohi J. Rheumatol. 21 1994 612
43. C. Wahl, S. Liptay, G. Adler, and R.M. Schmid J. Clin. Invest. 101 1998 1163
44. H. Masuda, Y. Takahashi, Y. Nishida, and S. Asai Eur. J. Clin. Pharmacol. 68 2012 1549
45. Kejha, J.; Brunova, B.; Slukova, D.; Kuchar, M.; Knezova, E.; Grimova, J. Eur. Patent 0,513,434 A1, November 19, 1992.
46. P.L. Wood, M.A. Khan, and J.R. Moskal Eur. J. Pharmacol. 580 2008 48
47. M.F. Reich, B.D. Johnson, R.H. Lenhard, and J.W. Hanifin Bioorg. Med. Chem. Lett. 4 1994 1167
48. G. Bendix, and A. Bjelle Ann. Rheum. Dis. 55 1996 169
49. M.W. Whitehouse, P.D. Cookson, G. Siasios, and E.R.T. Tiekink Met. Based Drugs 5 1998 245
50. J.L. Nam, S. Ramiro, C. Gaujoux-Viala, K. Takase, M. Leon-Garcia, P. Emery, L. Gossec, R. Landewe, J.S. Smolen, and M.H. Buch Ann. Rheum. Dis. 73 2014 516
51. S.L. Westlake, A.N. Colebatch, J. Baird, N. Curzen, P. Kiely, M. Quinn, E. Choy, A.J.K. Ostor, and C.J. Edwards Rheumatology 50 2011 518
52. P.V. Voulgari Expert Opin. Emerg. Drugs 13 2008 175
53. X. Chevalier, P. Goupille, A.D. Beaulieu, F.X. Burch, W.G. Bensen, T. Conrozier, D. Loeuille, A.J. Kivitz, D. Silver, and B.E. Appleton Arthritis Rheum. 61 2009 344
54. M.D. Magnano, E.F. Chakravarty, C. Broudy, L. Chung, A. Kelman, J. Hillygus, and M.C. Genovese J. Rheumatol. 34 2007 1323
55. A. Fioravanti, M. Fabbroni, A. Cerase, and M. Galeazzi Rheumatol. Int. 29 2009 961
56. H. Hashimoto, K. Imamura, J. Haruta, and K. Wakitani J. Med. Chem. 45 2002 1511
57. S.S. Shin, Y. Byun, K.M. Lim, J.K. Choi, Ki.-W. Lee, J.H. Moh, J.K. Kim, Y.S. Jeong, J.Y. Kim, Y.H. Choi, H.-Ju. Koh, Y.-Ho. Park, Y.I. Oh, M.-S. Noh, and S. Chung J. Med. Chem. 47 2004 792
58. Ji.-S. Shin, Y.-Su. Noh, M.-S. Yoo, J.-Y. Lee, Y.-W. Cho, and K.-T. Lee Bioorg. Med. Chem. Lett. 22 2012 2221
59. M. Inagaki, T. Tsuri, H. Jyoyama, T. Ono, K. Yamada, M. Kobayashi, Y. Hori, A. Arimura, K. Yasui, K. Ohno, S. Kakudo, K. Koizumi, R. Suzuki, S. Kawai, M. Kato, and S. Matsumoto J. Med. Chem. 43 2000 2040
60. M. Inagaki, H. Jyoyama, T. Ono, K. Yamada, M. Kobayashi, T. Baba, A. Touchi, K. Iwatani, T. Ohkawa, S. Matsumoto, and T. Tsuri Bioorg. Med. Chem. 11 2003 2415
61. K. Oda, T. Hida, T. Sakata, M. Nagai, Y. Sugata, T. Masui, and H. Nogusa Org. Proc. Res. Dev. 12 2008 442
62. M. Braddock Expert Opin. Investig. Drugs 14 2005 539
63. D. Steinhilber, and B. Hofmann Basic Clin. Pharmacol. Toxicol. 114 2014 70
64. L.A.B. Joosten, M.M.A. Helsen, T. Saxne, F.A.J. van de Loo, D. Heinegard, and W.B. van den Berg J. Immunol. 163 1999 5049
65. S. Krausz, M.J.H. Boumans, D.M. Gerlag, J. Lufkin, A.W.R. van Kuijk, A. Bakker, M. de Boer, B.M. Lodde, K.A. Reedquist, E.W. Jacobson, M. O'Meara, and P.P. Tak Arthritis Rheum. 64 2012 1750
66. S. Dhaneshwar, V. Patel, D. Patil, and G. Meena Bioorg. Med. Chem. Lett. 23 2013 55
67. B. Rintelen, K. Neumann, and B.F. Leeb Arch. Intern. Med. 166 2006 1899
68. S. Dhaneshwar, and D. Patil Bioorg. Med. Chem. Lett. 22 2012 7582
69. S.S. Dhaneshwar, R.S. Buchade, S. Vetal, H. Gautam, K.M. Tewari, and H.M. Karandikar Der Pharm. Chemi. 3 2011 354
70. S. DasGupta, P.R. Murumkar, R. Giridhar, and M.R. Yadav Bioorg. Med. Chem. 17 2009 444
71. M. Fujita, T. Seki, H. Inada, and N. Ikeda Bioorg. Med. Chem. Lett. 12 2002 1607
72. M. Fujita, T. Seki, and N. Ikeda Bioorg. Med. Chem. Lett. 12 2002 1897
73. J.J. Chen, N. Dewdney, X. Lin, R.L. Martin, K.A.M. Walker, J. Huang, F. Chu, E. Eugui, A. Mirkovich, Y. Kim, K. Sarma, H. Arzeno, and H.E. Van Wart Bioorg. Med. Chem. Lett. 13 2003 3951
74. J.I. Levin, J.M. Chen, L.M. Laakso, M. Du, X. Du, A.M. Venkatesan, V. Sandanayaka, A. Zask, J. Xu, W. Xu, Y. Zhang, and J.S. Skotnicki Bioorg. Med. Chem. Lett. 15 2005 4345
75. M.L. Moss, L. Sklair-Tavron, and R. Nudelman Nat. Clin. Pract. Rheumatol. 4 2008 300
76. V. Aranapakam, J.M. Davis, G.T. Grosu, J. Baker, J. Ellingboe, A. Zask, J.I. Levin, V.P. Sandanayaka, M. Du, J.S. Skotnicki, J.F. DiJoseph, A. Sung, M.A. Sharr, L.M. Killar, T. Walter, G. Jin, R. Cowling, J. Tillett, W. Zhao, J. McDevitt, and Z.B. Xu J. Med. Chem. 46 2003 2376
77. Y. Hu, J.S. Xiang, M.J. DiGrandi, X. Du, M. Ipek, L.M. Laakso, J. Li, W. Li, T.S. Rush, J. Schmid, J.S. Skotnicki, S. Tam, J.R. Thomason, Q. Wang, and J.I. Levin Bioorg. Med. Chem. 13 2005 6629
78. J.J. Li, J. Nahra, A.R. Johnson, A. Bunker, P. O'Brien, W.-S. Yue, D.F. Ortwine, C.-F. Man, V. Baragi, K. Kilgore, R.D. Dyer, and H.-K. Han J. Med. Chem. 51 2008 835
79. R.L. Leff Ann. N. Y. Acad. Sci. 878 1999 201
80. P. Krzeski, C. Buckland-Wright, G. Bálint, G.A. Cline, K. Stoner, R. Lyon, J. Beary, W.S. Aronstein, and T.D. Spector Arthritis Res. Ther. 9 2007 R109
81. A.V. Miagkov, D.V. Kovalenko, C.E. Brown, J.R. Didsbury, J.P. Cogswell, S.A. Stimpson, A.S. Baldwin, and S.S. Makarov Proc. Natl. Acad. Sci. U.S.A. 95 1998 13859
82. N. Matsumoto, A. Ariga, S. To-e, H. Nakamura, N. Agata, S. Hirano, J. Inoue, and K. Umezawa Bioorg. Med. Chem. Lett. 10 2000 865
83. R.J. Steffan, E. Matelan, M.A. Ashwell, W.J. Moore, W.R. Solvibile, E. Trybulski, C.C. Chadwick, S. Chippari, T. Kenney, A. Eckert, L. Borges-Marcucci, J.C. Keith, Z. Xu, L. Mosyak, and D.C. Harnish J. Med. Chem. 47 2004 6435
84. Y. Aikawa, M. Yamamoto, T. Yamamoto, K. Morimoto, and K. Tanaka Inflamm. Res. 51 2002 188
85. T. Inaba, K. Tanaka, R. Takeno, H. Nagaki, C. Yoshida, and S. Takano Chem. Pharm. Bull. 48 2000 131
86. F. Du, L. Lü, Q. Fu, M. Dai, J.-Ie. Teng, W. Fan, S.-I. Chen, P. Ye, N. Shen, X. Huang, J. Qian, and C. Bao Arthritis Res. Ther. 10 2008 R136
87. T.J. Caggiano, A. Brazzale, D.M. Ho, C.M. Kraml, E. Trybulski, C.C. Chadwick, S. Chippari, L. Borges-Marcucci, A. Eckert, J.C. Keith, T. Kenney, and D.C. Harnish J. Med. Chem. 50 2007 5245
88. J.A. Roman-Blas, S. Castañeda, R. Largo, and G. Herrero-Beaumont Arthritis Res. Ther. 11 2009 241
89. M.C. Genovese Arthritis Rheum. 60 2009 317
90. C.J. Malemud Mini Rev. Med. Chem. 6 2006 689
91. L.H. Pettus, S. Xu, G.-Q. Cao, P.P. Chakrabarti, R.M. Rzasa, K. Sham, R.P. Wurz, D. Zhang, S. Middleton, B. Henkle, M.H. Plant, C.J.M. Saris, L. Sherman, Lu M. Wong, D.A. Powers, Y. Tudor, V. Yu, M.R. Lee, R. Syed, F. Hsieh, and A.S. Tasker J. Med. Chem. 51 2008 6280
92. S.E. de Laszlo, D. Visco, L. Agarwal, L. Chang, J. Chin, G. Croft, A. Forsyth, D. Fletcher, B. Frantz, C. Hacker, W. Hanlon, C. Harper, M. Kostura, B. Li, S. Luell, M. MacCoss, N. Mantlo, E.A. O'Neill, C. Orevillo, M. Pang, J. Parsons, A. Rolando, Y. Sahly, K. Sidler, W.R. Widmer, and S.J. O'Keefe Bioorg. Med. Chem. Lett. 8 1998 2689
93. J. Dumas, H. Hatoum-Mokdad, R.N. Sibley, R.A. Smith, W.J. Scott, U. Khire, W. Lee, J. Wood, D. Wolanin, J. Cooley, D. Bankston, A.M. Redman, R. Schoenleber, Y. Caringal, D. Gunn, R. Romero, M. Osterhout, H. Paulsen, T.J. Housley, S.M. Wilhelm, J. Pirro, Du.-S. Chien, G.E. Ranges, A. Shrikhande, A. Muzsi, E. Bortolon, J. Wakefield, C. Gianpaolo Ostravage, A. Bhargava, and T. Chau Bioorg. Med. Chem. Lett. 12 2002 1559
94. L. Revesz, E. Blum, F.E. Di Padova, T. Buhl, R. Feifel, H. Gram, P. Hiestand, U. Manning, and G. Rucklin Bioorg. Med. Chem. Lett. 14 2004 3595
95. L. Revesz, E. Blum, F.E. Di Padova, T. Buhl, R. Feifel, H. Gram, P. Hiestand, U. Manning, and G. Rucklin Bioorg. Med. Chem. Lett. 14 2004 3601
96. N. Tamayo, L. Liao, M. Goldberg, D. Powers, Y.-Y. Tudor, V. Yu, Lu M. Wong, B. Henkle, S. Middleton, R. Syed, T. Harvey, G. Jang, R. Hungate, and C. Dominguez Bioorg. Med. Chem. Lett. 15 2005 2409
97. B. Devadas, S.R. Selness, L. Xing, H.M. Madsen, L.D. Marrufo, H. Shieh, D.M. Messing, J.Z. Yang, H.M. Morgan, G.D. Anderson, E.G. Webb, J. Zhang, R.V. Devraj, and J.B. Monahan Bioorg. Med. Chem. Lett. 21 2011 3856
98. J. Aiguadé, C. Balagué, I. Carranco, F. Caturla, M. Domínguez, P. Eastwood, C. Esteve, J. González, W. Lumeras, A. Orellana, S. Preciado, R. Roca, L. Vidal, and B. Vidal Bioorg. Med. Chem. Lett. 22 2012 3431
99. A.M. Badger, J.N. Bradbeer, B. Votta, J.C. Lee, J.L. Adams, and D.E. Griswold J. Pharmacol. Exp. Ther. 279 1996 1453
100. S.B. Cohen, T.-T. Cheng, V. Chindalore, N. Damjanov, R. Burgos-Vargas, P. DeLora, K. Zimany, H. Travers, and J.P. Caulfield Arthritis Rheum. 60 2009 335
101. N. Damjanov, R.S. Kauffman, and G.T. Spencer-Green Arthritis Rheum. 60 2009 1232
102. M.C. Genovese, S.B. Cohen, D. Wofsy, M.E. Weinblatt, G.S. Firestein, E. Brahn, V. Strand, D.G. Baker, and S.E. Tong J. Rheumatol. 38 2011 846
103. M.E. McDonnell, H. Bian, J. Wrobel, G.R. Smith, S. Liang, H. Ma, and A.B. Reitz Bioorg. Med. Chem. Lett. 24 2014 1116
104. A. Kontzias, A. Kotlyar, A. Laurence, P. Changelian, and J.J. O'Shea Curr. Opin. Pharmacol. 12 2012 464
105. R. Fleischmann, J. Kremer, J. Cush, H. Schulze-Koops, C.A. Connell, J.D. Bradley, D. Gruben, G.V. Wallenstein, S.H. Zwillich, and K.S.N. Kanik Engl. J. Med. 367 2012 495
106. R. Fleischmann, M. Cutolo, M.C. Genovese, E.B. Lee, K.S. Kanik, S. Sadis, C.A. Connell, D. Gruben, S. Krishnaswami, G. Wallenstein, B.E. Wilkinson, and S.H. Zwillich Arthritis Rheum. 64 2012 617
107. H.-S. Cha, D.L. Boyle, T. Inoue, R. Schoot, P.P. Tak, P. Pine, and G.S. Firestein J. Pharmacol. Exp. Ther. 317 2006 571
108. M.E. Weinblatt, A. Kavanaugh, R. Burgos-Vargas, A.H. Dikranian, G. Medrano-Ramirez, J.L. Morales-Torres, F.T. Murphy, T.K. Musser, N. Straniero, A.V. Vicente-Gonzales, and E. Grossbard Arthritis Rheum. 58 2008 3309
109. M.E. Weinblatt, A. Kavanaugh, M.C. Genovese, T.K. Musser, E.B. Grossbard, and D.B.N. Magilavy Engl. J. Med. 363 2010 1303
110. G. Liu, B.T. Campbell, M.W. Holladay, J.M. Ford Pulido, H. Hua, D. Gitnick, M.F. Gardner, J. James, M.A. Breider, D. Brigham, B. Belli, R.C. Armstrong, and D.K. Treiber ACS Med. Chem. Lett. 3 2012 997
111. C.R. Illig, C.L. Manthey, M.J. Wall, S.K. Meegalla, J. Chen, K.J. Wilson, S.K. Ballentine, R.L. DesJarlais, C. Schubert, C.S. Crysler, Y. Chen, C.J. Molloy, M.A. Chaikin, R.R. Donatelli, E. Yurkow, Z. Zhou, M.R. Player, and B.E. Tomczuk J. Med. Chem. 54 2011 7860
112. C.E. Vergunst, D.M. Gerlag, L. von Moltke, M. Karol, T. Wyant, X. Chi, E. Matzkin, T. Leach, and P.P. Tak Arthritis Rheum. 60 2009 3572
113. L. Revesz, B. Bollbuck, T. Buhl, J. Eder, R. Esser, R. Feifel, R. Heng, P. Hiestand, B. Jachez-Demange, P. Loetscher, H. Sparrer, A. Schlapbach, and R. Waelchli Bioorg. Med. Chem. Lett. 15 2005 5160
114. L. Revesz, B. Bollbuck, T. Buhl, J. Dawson, R. Feifel, R. Heng, P. Hiestand, H. Sparrer, A. Schlapbach, and R. Waelchli Lett. Drug Des. Discov. 3 2006 689
115. Y.F. Xie, K. Lake, K. Ligsay, M. Komandla, I. Sircar, G. Nagarajan, J. Li, K. Xu, J. Parise, L. Schneider, D. Huang, J. Liu, K. Dines, N. Sakurai, M. Barbosa, and R. Jack Bioorg. Med. Chem. Lett. 17 2007 3367
116. J. Martel-Pelletier, L.M. Wildi, and J.-P. Pelletier Bone 51 2012 297
117. N. Katz, D.G. Borenstein, C. Birbara, C. Bramson, M.A. Nemeth, M.D. Smith, and M.T. Brown Pain 152 2011 2248
118. N.E. Lane, T.J. Schnitzer, C.A. Birbara, M. Mokhtarani, D.L. Shelton, M.D. Smith, and M.T.N. Brown Engl. J. Med. 363 2010 1521
119. H. Nagashima, M. Suzuki, S. Araki, T. Yamabe, and C. Muto Osteoarthr. Cartilage 19 2011 1405
120. T.J. Schnitzer, N.E. Lane, C. Birbara, M.D. Smith, S.L. Simpson, and M.T. Brown Osteoarthr. Cartilage 19 2011 639
121. M.T. Brown, F.T. Murphy, D.M. Radin, I. Davignon, M.D. Smith, and C.R. West J. Pain 13 2012 790
122. E.L. Spierings, J. Fidelholtz, G. Wolfram, M.D. Smith, M.T. Brown, and C.R. West Pain 154 2013 1603
123. P.J. Tiseo, A.J. Kivitz, J.E. Ervin, H. Ren, and S. Mellis J. Pain 155 2014 1245
124. J.T. Bagdanoff, M.S. Donoviel, A. Nouraldeen, M. Carlsen, T.C. Jessop, J. Tarver, S. Aleem, L. Dong, H. Zhang, L. Boteju, J. Hazelwood, J. Yan, M. Bednarz, S. Layek, I.B. Owusu, S. Gopinathan, L. Moran, Z. Lai, J. Kramer, S.D. Kimball, P. Yalamanchili, W.E. Heydorn, K.S. Frazier, B. Brooks, P. Brown, A. Wilson, W.K. Sonnenburg, A. Main, K.G. Carson, T. Oravecz, and D.J. Augeri J. Med. Chem. 53 2010 8650
125. M.H. Silverman, V. Strand, D. Markovits, M. Nahir, T. Reitblat, Y. Molad, I. Rosner, M. Rozenbaum, R. Mader, M. Adawi, D. Caspi, M. Tishler, P. Langevitz, A. Rubinow, J. Friedman, L. Green, A. Tanay, A. Ochaion, S. Cohen, W.D. Kerns, I. Cohn, S. Fishman-Furman, M. Farbstein, S.B. Yehuda, and P. Fishman J. Rheumatol. 35 2008 41
126. S. Bar-Yehuda, L. Rath-Wolfson, L. Del Valle, A. Ochaion, S. Cohen, R. Patoka, G. Zozulya, F. Barer, E. Atar, S. Piña-Oviedo, G. Perez-Liz, D. Castel, and P. Fishman Arthritis Rheum. 60 2009 3061
127. J.A. Roman-Blas, and S.A. Jimenez Osteoarthr. Cartilage 14 2006 839
128. M.S. Plummer, J. Cornicelli, H. Roark, D.J. Skalitzky, C.J. Stankovic, S. Bove, J. Pandit, A. Goodman, J. Hicks, A. Shahripour, D. Beidler, X.K. Lu, B. Sanchez, C. Whitehead, R. Sarver, T. Braden, R. Gowan, X.Q. Shen, K. Welch, A. Ogden, N. Sadagopan, H. Baum, H. Miller, C. Banotai, C. Spessard, and S. Lightle Bioorg. Med. Chem. Lett. 23 2013 3443
129. T.J. Schnitzer, A. Kivitz, H. Frayssinet, and B. Duquesroix Osteoarthr. Cartilage 18 2010 629
130. T.J. Schnitzer, M.C. Hochberg, C.E. Marrero, B. Duquesroix, H. Frayssinet, and M. Beekman Semin. Arthritis Rheum. 40 2011 285
131. J.P. Brown, and L.J. Boulay Ther. Adv. Musculoskelet. Dis. 5 2013 291
132. M.P. Hellio le Graverand, R.S. Clemmer, P. Redifer, R.M. Brunell, C.W. Hayes, K.D. Brandt, S.B. Abramson, P.T. Manning, C.G. Miller, and E. Vignon Ann. Rheum. Dis. 72 2013 187
133. K.D. Brandt, S.A. Mazzuca, B.P. Katz, K.A. Lane, K.A. Buckwalter, D.E. Yocum, F. Wolfe, T.J. Schnitzer, L.W. Moreland, S. Manzi, J.D. Bradley, L. Sharma, C.V. Oddis, S.T. Hugenberg, and L.W. Heck Arthritis Rheum. 52 2005 2015
134. J.-Y. Reginster, J. Badurski, N. Bellamy, W. Bensen, R. Chapurlat, X. Chevalier, C. Christiansen, H. Genant, F. Navarro, E. Nasonov, P.N. Sambrook, T.D. Spector, and C. Cooper Ann. Rheum. Dis. 72 2013 179
135. P. Rajakumar, and R. Padmanabhan Aust. J. Chem. 65 2012 186
136. P. Rajakumar, R. Padmanabhan, and N. Rajesh Bioorg. Med. Chem. Lett. 22 2012 3770
137. S.M. Nanjundaiah, B. Astry, and K.D. Moudgil Evid. Based Complement Alternat. Med. 2013 2013 518094
138. D. Khanna, G. Sethi, K.S. Ahn, M.K. Pandey, A.B. Kunnumakkara, B. Sung, A. Aggarwal, and B.B. Aggarwal Curr. Opin. Pharmacol. 7 2007 344
139. M.C. Recio, I. Andujar, and J.L. Rios Curr. Med. Chem. 19 2012 2088
140. C.L.H. Yang, T.C.T. Or, M.H.K. Ho, and A.S.Y. Lau Clin. Rev. Allergy Immunol. 44 2013 284
141. S. Chen, Y. Yang, H. Feng, H. Wang, R. Zhao, and H. Liu Inflammation 37 2014 163
142. X. Yang, J. Yang, and H. Zou Clin. Dev. Immunol. 2013 2013 268065
143. N. Chalasani, R. Vuppalanchi, V. Navarro, R. Fontana, H. Bonkovsky, H. Barnhart, D.E. Kleiner, and J.H. Hoofnagle Ann. Intern. Med. 156 2012 857
144. B.P. Burnett, A. Bitto, D. Altavilla, F. Squadrito, R.M. Levy, and L. Pillai Mediators Inflamm. 2011 2011 385780
145. R.M. Levy, A. Khokhlov, S. Kopenkin, B. Bart, T. Ermolova, R. Kantemirova, V. Mazurov, M. Bell, P. Caldron, L. Pillai, and B.P. Burnett Adv. Ther. 27 2010 731
146. R. Levy, A. Khokhlov, S. Kopenkin, B. Bart, T. Ermolova, R. Kantemirova, V. Mazurov, M. Bell, P. Caldron, L. Pillai, and B. Burnett Adv. Ther. 27 2010 953
147. J.-H. Lee, and Y. Han Arch. Pharm. Res. 34 2011 853
148. J.-E. Huh, In.-T. Jung, J. Choi, Y.-H. Baek, J.-D. Lee, D.-S. Park, and Do.-Y. Choi Eur. J. Pharmacol. 698 2013 57
149. T. Guardia, A.E. Rotelli, A.O. Juarez, and L.E. Pelzer Farmaco 56 2001 683
150. S. Umar, A. Kumar, M. Sajad, J. Zargan, M. Ansari, S. Ahmad, C.K. Katiyar, and H.A. Khan Rheumatol. Int. 33 2013 657
151. K. Kawaguchi, H. Maruyama, R. Hasunuma, and Y. Kumazawa Immunopharmacol. Immunotoxicol. 33 2011 723
152. Y.-R. Lee, J.-Ki. Hwang, H.-W. Koh, K.Y. Jang, J.H. Lee, J.-W. Park, and B.-H. Park Life Sci. 90 2012 799
153. J. Li, D. Gang, X. Yu, Y. Hu, Y. Yue, W. Cheng, X. Pan, and P. Zhang Clin. Rheumatol. 32 2013 535
154. M. Mohammad-Shahi, F. Haidari, B. Rashidi, A.A. Saei, S. Mahboob, and M.-R. Rashidi Bioimpacts 1 2011 161
155. S. Ahmed, A. Rahman, A. Hasnain, M. Lalonde, V.M. Goldberg, and T.M. Haqqi Free Radic. Biol. Med. 33 2002 1097
156. R. Singh, N. Akhtar, and T.M. Haqqi Life Sci. 86 2010 907
157. C. Braicu, M.R. Ladomery, V.S. Chedea, A. Irimie, and I. Berindan-Neagoe Food Chem. 141 2013 3282
158. A. Morinobu, W. Biao, S. Tanaka, M. Horiuchi, L. Jun, G. Tsuji, Y. Sakai, M. Kurosaka, and S. Kumagai Arthritis Rheum. 2008 2012 58
159. M. Shakibaei, C. Csaki, S. Nebrich, and A. Mobasheri Biochem. Pharmacol. 76 2008 1426
160. A. Mobasheri, Y. Henrotin, H.-K. Biesalski, and M. Shakibaei Int. J. Mol. Sci. 13 2012 4202
161. N. Elmali, I. Esenkaya, A. Harma, K. Ertem, Y. Turkoz, and B. Mizrak Inflamm. Res. 54 2005 158
162. G. Xuzhu, M. Komai-Koma, B.P. Leung, H.S. Howe, C. McSharry, I.B. McInnes, and D. Xu Ann. Rheum. Dis. 71 2012 129
163. X. Fan, C. Zhang, D. Liu, J. Yan, and H. Liang Curr. Pharm. Des. 2013 2011 19
164. A.F. Zahidah, O. Faizah, K. Nur Aqilah, and K. Taty Anna Sains Malaysiana 41 2012 591
165. G. Huang, Z. Xu, Y. Huang, X. Duan, W. Gong, Y. Zhang, J. Fan, and F. He J. Clin. Immunol. 33 2013 550
166. G. Belcaro, M.R. Cesarone, M. Dugall, L. Pellegrini, A. Ledda, M.G. Grossi, S. Togni, and G. Appendino Panminerva Med. 52 2010 55
167. B. Chandran, and A. Goel Phytother. Res. 26 2012 1719
168. M.A. Khan, R. El-Khatib, K.D. Rainsford, and M.W. Whitehouse Bioorg. Chem. 40 2012 30
169. M.E. Munroe, J.L. Arbiser, and G.A. Bishop J. Immunol. 179 2007 753
170. K.R. Kim, K.-K. Park, K.-S. Chun, and W.-Y. Chung J. Pharmacol. Sci. 114 2010 69
171. R. Grespan, M. Paludo, H. de Paula Lemos, C.P. Barbosa, C.A. Bersani-Amado, M.M. de Oliveira Dalalio, and R.K.N. Cuman Biol. Pharm. Bull. 35 2012 1818
172. S.-Ik. Lee, P.-Mi. Hyun, S.-H. Kim, K.-S. Kim, S.-K. Lee, B.-S. Kim, P.J. Maeng, and J.S. Lim Arthritis Rheum. 52 2005 345
173. Z.J. Zhai, H.W. Li, G.W. Liu, X.H. Qu, B. Tian, W. Yan, Z. Lin, T.T. Tang, A. Qin, and K.R. Dai Br. J. Pharmacol. 171 2014 663
174. R.A. Burgos, J.L. Hancke, J.C. Bertoglio, V. Aguirre, S. Arriagada, M. Calvo, and D.D. Cáceres Clin. Rheumatol. 28 2009 931
175. H.R. Siddique, and M. Saleem Life Sci. 88 2011 285
176. V. Saratha, and S.P. Subramanian Inflammopharmacology 20 2012 27
177. T. Geetha, and P. Varalakshmi J. Ethnopharmacol. 76 2001 77
178. G. Kweifio-Okai, F. De Munk, T.A. Macrides, P. Smith, and B.A. Rumble Drug Dev. Res. 36 1995 20
179. R. Kannaiyan, M.K. Shanmugam, and G. Sethi Cancer Lett. 303 2011 9
180. Fu.-C. Huang, W.-K. Chan, K.J. Moriarty, De.-C. Zhang, M.N. Chang, W. He, K.-T. Yu, and A. Zilberstein Bioorg. Med. Chem. Lett. 1998 1883 8
181. S.H. Venkatesha, B. Astry, S.M. Nanjundaiah, H. Yu, and K.D. Moudgil Bioorg. Med. Chem. 20 2012 5229
182. S.M. Nanjundaiah, S.H. Venkatesha, H. Yu, L. Tong, J.P. Stains, and K.D. Moudgil J. Biol. Chem. 287 2012 22216
183. S.-Y. Kang, S.-Y. Yoon, D.-H. Roh, Mi.-J. Jeon, H.-S. Seo, D.-K. Uh, Y.-B. Kwon, H.-W. Kim, Ho.-J. Han, H.-J. Lee, and J.-H. Lee J. Pharm. Pharmacol. 60 2008 1347
184. M. Abdel-Tawab, O. Werz, and M. Schubert-Zsilavecz Clin. Pharmacokinet. 50 2011 349
185. S. Singh, A. Khajuria, S.C. Taneja, R.K. Johri, J. Singh, and G.N. Qazi Phytomedicine 15 2008 400
186. R. Etzel Phytomedicine 3 1996 91
187. O. Sander, G. Herborn, and R. Rau Z. Rheumatol. 57 1998 11
188. N. Kimmatkar, V. Thawani, L. Hingorani, and R. Khiyani Phytomedicine 10 2003 3
189. S. Sontakke, V. Thawani, S. Pimpalkhute, P. Kabra, S. Babhulkar, and L. Hingorani Indian J. Pharmacol. 39 2007 27
190. K. Sengupta, K.V. Alluri, A.R. Satish, S. Mishra, T. Golakoti, K.V.S. Sarma, D. Dey, and S.P. Raychaudhuri Arthritis Res. Ther. 10 2008 R85
191. K. Sengupta, A.V. Krishnaraju, A.A. Vishal, A. Mishra, G. Trimurtulu, K.V.S. Sarma, S.K. Raychaudhuri, and S.P. Raychaudhuri Int. J. Med. Sci. 7 2010 366
192. K. Sengupta, J.N. Kolla, A.V. Krishnaraju, N. Yalamanchili, C.V. Rao, T. Golakoti, S. Raychaudhuri, and S.P. Raychaudhuri Mol. Cell. Biochem. 354 2011 189
193. S.K. Das, S. Ramakrishnan, K. Mishra, R. Srivastava, G.G. Agarwal, R. Singh, and A.R. Sircar Arthritis Rheum. 47 2002 280
194. S.-J. Lee, W.-D. Nam, H.-J. Na, Y.-L. Cho, K.-S. Ha, J.-Y. Hwang, H. Lee, S.-Ok. Kim, Y.-G. Kwon, and Y.-M. Kim Biochem. Pharmacol. 76 2008 79
195. T.J. Schnitzer, J.-P. Pelletier, D.M. Haselwood, W.T. Ellison, J.E. Ervin, R.D. Gordon, J.R. Lisse, W.T. Archambault, A.R. Sampson, H.B. Fezatte, S.B. Phillips, and J.E. Bernstein J. Rheumatol. 39 2012 610
196. R. Remadevi, and A. Szallisi IDrugs 11 2008 120
197. J.O. Ban, J.H. Oh, T.M. Kim, D.J. Kim, H.S. Jeong, S.B. Han, and J.T. Hong Arthritis Res. Ther. 11 2009 R145
198. A.Y. Imanaeva, L.N. Zalyalyutdinova, and D.E. Tsyplakov Fundamental Research 6 2013 596
199. B.B. Singh, L.C. Mishra, S.P. Vinjamury, N. Aquilina, V.J. Singh, and N. Shepard Altern. Ther. Health Med. 9 2003 74
200. Y.-B. Jung, S.-C. Seong, M.-C. Lee, Y.-Un. Shin, D.-H. Kim, J.-M. Kim, Y.-K. Jung, J.-H. Ahn, J.-G. Seo, Y.-S. Park, C.-S. Lee, K.-J. Roh, C.-K. Han, Y.-B. Cho, D.-Y. Chang, W.-J. Kwak, K.-O. Jung, and B.-J. Park Am. J. Chin. Med. 32 2004 291
201. R. Grzanna, L. Lindmark, and C.G. Frondoza J. Med. Food 8 2005 125
202. H. Bliddal, A. Rosetzsky, P. Schlichting, M.S. Weidner, L.A. Andersen, H.-H. Ibfelt, K. Christensen, O.N. Jensen, and J. Barslev Osteoarthr. Cartilage 8 2000 9
203. R.D. Altman, and K.C. Marcussen Arthritis Rheum. 44 2001 2531
204. I. Wigler, I. Grotto, D. Caspi, and M. Yaron Osteoarthr. Cartilage 11 2003 783
205. L.G. Ameye, and W.S.S. Chee Arthritis Res. Ther. 8 2006 R127
206. H.L. Lopez PM R 4 2012 S155
207. W.B. Jonas, C.P. Rapoza, and W.F. Blair Inflamm. Res. 45 1996 330
208. N.H. Jensen Ugeskr. Laeger. 165 2003 2563
209. Y. Cao, G. Jones, F. Cicuttini, T. Winzenberg, A. Wluka, J. Sharman, K. Nguo, and C. Ding Trials 13 2012 131
210. R. Hesslink Jr., D. Armstrong III, M.V. Nagendran, S. Sreevatsan, and R. Barathur J. Rheumatol. 29 2002 1708
211. C. Boileau, J. Martel-Pelletier, J. Caron, P. Msika, G.B. Guillou, C. Baudouin, and J.-P. Pelletier Arthritis Res. Ther. 11 2009 R41
212. E. Ernst Clin. Rheumatol. 22 2003 285
213. G. Klein, and W. Kullich Clin. Drug Invest. 19 2000 15
214. N.M. Akhtar, R. Naseer, A.Z. Farooqi, W. Aziz, and M. Nazir Clin. Rheumatol. 23 2004 410
215. G. Vetter Am. J. Med. 83 1987 78
216. L.S. Kim, L.J. Axelrod, P. Howard, N. Buratovich, and R.F. Waters Osteoarthr. Cartilage 14 2006 286
217. P.R. Usha, and M.U.R. Naidu Clin. Drug Invest. 24 2004 353
218. J. Gruenwald, E. Petzold, R. Busch, H.-P. Petzold, and H.-J. Graubaum Adv. Ther. 26 2009 858
219. Y.H. Lee, J.-H. Woo, S.J. Choi, J.D. Ji, and G.G. Song Rheumatol. Int. 30 2010 357
220. D.S. Kalman, M. Heimer, A. Valdeon, H. Schwartz, and E. Sheldon Nutr. J. 7 2008 3
221. A. Homma, H. Sato, A. Okamachi, T. Emura, T. Ishizawa, T. Kato, T. Matsuura, S. Sato, T. Tamura, Y. Higuchi, T. Watanabe, H. Kitamura, K. Asanuma, T. Yamazaki, M. Ikemi, H. Kitagawa, T. Morikawa, H. Ikeya, K. Maeda, K. Takahashi, K. Nohmi, N. Izutani, M. Kanda, and R. Suzuki Bioorg. Med. Chem. 17 2009 4647