Oral bioavailability, efficacy and gastric tolerability of P2026, a novel nitric oxide-releasing diclofenac in rat

Inflammopharmacology

Volumn 18, Issue 4, 2010, Pages 157-168

  Pathan, Asif R ^a   Karwa, Manoj ^b   Pamidiboina, Venu ^c   Deshattiwar, Jagannath J ^d   Deshmukh, Nitin J ^e   Gaikwad, Parikshit P ^e   Mali, Sunil V ^e   Desai, Dattatraya C ^e   Dhiman, Mini ^e   Thanga Mariappan, T ^f   Sharma, Somesh D ^e   Satyam, Apparao ^e   Nemmani, Kumar V S ^e  

^a UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

^b Auriga Research Limited   (India)

^c Ranbaxy Laboratories Limited   (India)

^d Government of Maharashtra   (India)

^e Piramal Enterprises Limited   (India)

^f Biocon Bristol Meyer Squibb Research Centre   (India)

Author keywords

Anti inflammatory activity; Gastric ulcer; NO diclofenac; Prostaglandin

Indexed keywords

2 [[2 (NITROOXY)ETHYL]DISULFANYL]ETHYL 2 [2 (2,6 DICHLOROPHENYLAMINO)PHENYL]ACETATE; DICLOFENAC; DICLOFENAC DERIVATIVE; INTERLEUKIN 1BETA; INTERLEUKIN 6; LIPOPOLYSACCHARIDE; NITRATE; NITRIC OXIDE; NITRITE; P 2026; PROSTACYCLIN; PROSTAGLANDIN E2; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTHRITIS; ARTICLE; CONTROLLED STUDY; CYTOKINE PRODUCTION; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG EFFICACY; DRUG SAFETY; DRUG STRUCTURE; DRUG TOLERABILITY; GASTROINTESTINAL TOXICITY; INFLAMMATION; MALE; NONHUMAN; PAW EDEMA; PHARMACODYNAMICS; PRIORITY JOURNAL; PROSTAGLANDIN SYNTHESIS INHIBITION; RAT; SEPTIC SHOCK; STOMACH ULCER;

ADMINISTRATION, ORAL; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ARTHRITIS, EXPERIMENTAL; BIOLOGICAL AVAILABILITY; CYCLOOXYGENASE INHIBITORS; DICLOFENAC; DINOPROSTONE; DRUG EVALUATION, PRECLINICAL; EPOPROSTENOL; INFLAMMATION; MALE; NITRATES; NITRIC OXIDE; NITRIC OXIDE DONORS; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY; STOMACH; STOMACH ULCER;

EID: 77955647592     PISSN: 09254692     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10787-010-0043-7     Document Type: Article

References (33)

1. O al-Swayeh R Clifford P del Soldato, et al. 2000 A comparison of the anti-inflammatory and anti-nociceptive activity of nitroaspirin and aspirin Br J Pharmacol 129 2 343 350 10.1038/sj.bjp.0703064 1:CAS:528:DC%2BD3cXpslyrtg%3D%3D 10694241 (Pubitemid 30072655)
2. CB Appleyard, et al. 1996 Tumor necrosis factor mediation of NSAID-induced gastric damage: role of leukocyte adherence Am J Physiol Gastrointest Liver Physiol 270 G42 G48 1:CAS:528:DyaK28XhtVynsbw%3D
3. T Brzozowski P Konturek S Konturek, et al. 2000 Gastroprotective and ulcer healing effects of nitric oxide-releasing non-steroidal anti-inflammatory drugs Dig Liver Dis 32 7 583 594 10.1016/S1590-8658(00)80840-3 1:CAS:528:DC%2BD3MXhsVGm 11142556
4. T Brzozowski P Konturek S Konturek, et al. 2005 Role of prostaglandins in gastroprotection and gastric adaptation J Physiol Pharmacol 56 Suppl 5 33 55 16247188
5. C Cho 2001 Current roles of nitric oxide in gastrointestinal disorders J Physiol Paris 95 1-6 253 256 10.1016/S0928-4257(01)00034-1 1:CAS:528: DC%2BD3MXot1Sgu7s%3D 11595446 (Pubitemid 33020246)
6. N Davies A Røseth C Appleyard, et al. 1997 NO-naproxen vs naproxen: ulcerogenic, analgesic and anti-inflammatory effects Aliment Pharmacol Ther 11 1 69 79 10.1046/j.1365-2036.1997.115286000.x 1:CAS:528: DyaK2sXhvVShtrg%3D 9042976
7. S Elliott W McKnight G Cirino, et al. 1995 A nitric oxide-releasing nonsteroidal anti-inflammatory drug accelerates gastric ulcer healing in rats Gastroenterology 109 2 524 530 10.1016/0016-5085(95)90341-0 1:CAS:528: DyaK2MXntlCgtb8%3D 7615202
8. R Fannin J Auman M Bruno, et al. 2005 Differential gene expression profiling in whole blood during acute systemic inflammation in lipopolysaccharide-treated rats Physiol Genomics 21 1 92 104 10.1152/physiolgenomics.00190.2004 1:CAS:528:DC%2BD2MXjtFyhs78%3D 15781589 (Pubitemid 40898468)
9. S Fiorucci E Antonell 2006 NO-NSAIDs: from inflammatory mediators to clinical readouts Inflamm Allergy Drug Targets 5 2 121 131 10.2174/ 187152806776383161 1:CAS:528:DC%2BD28XlsVGqtrY%3D 16613571
10. S Fiorucci E Antonelli L Santucci, et al. 1999 Gastrointestinal safety of nitric oxide-derived aspirin is related to inhibition of ICE-like cysteine proteases in rats Gastroenterology 116 5 1089 1106 10.1016/S0016-5085(99)70012-0 1:CAS:528:DyaK1MXjtVGisb4%3D 10220501 (Pubitemid 29203019)
11. S Fiorucci E Antonelli J Burgaud, et al. 2001 Nitric oxide-releasing NSAIDs: a review of their current status Drug Saf 24 11 801 811 10.2165/00002018-200124110-00002 1:CAS:528:DC%2BD3MXnvVanu7o%3D 11665868
12. 2S-releasing NSAIDs: what lies beyond the horizon Dig Liver Dis 39 12 1043 1051 10.1016/j.dld.2007.09.001 1:CAS:528:DC%2BD1cXisVOjtL0%3D 17997373 (Pubitemid 350131544)
13. M Fratelli M Minto A Crespi, et al. 2003 Inhibition of nuclear factor-kappaB by a nitro-derivative of flurbiprofen: a possible mechanism for antiinflammatory and antiproliferative effect Antioxid Redox Signal 5 2 229 235 10.1089/152308603764816587 1:CAS:528:DC%2BD3sXjtFKnurg%3D 12716482
14. Gutiérrez-Cabano CA (2000) Protection by intragastric polyethylene glycol 400 in rat stomach against ethanol damage involves alpha2-adrenoceptors. Dig Dis Sci 45(1):105-109
15. J Keeble P Moore 2002 Pharmacology and potential therapeutic applications of nitric oxide-releasing non-steroidal anti-inflammatory and related nitric oxide-donating drugs Br J Pharmacol 137 3 295 310 10.1038/sj.bjp.0704876 1:CAS:528:DC%2BD38Xns1Ciur0%3D 12237248
16. P Konturek T Brzozowski J Kania, et al. 2003 Nitric oxide-releasing aspirin protects gastric mucosa against ethanol damage in rats with functional ablation of sensory nerves Inflamm Res 52 9 359 365 10.1007/s00011-003-1183-7 1:CAS:528:DC%2BD3sXnvFGkur8%3D 14504662 (Pubitemid 37130002)
17. L Li G Rossoni A Sparatore, et al. 2007 Anti-inflammatory and gastrointestinal effects of a novel diclofenac derivative Free Radic Biol Med 42 5 706 719 10.1016/j.freeradbiomed.2006.12.011 17291994 (Pubitemid 46205152)
18. P Minuz M Degan S Gaino, et al. 2001 NCX4016 (NO-Aspirin) has multiple inhibitory effects in LPS-stimulated human monocytes Br J Pharmacol 134 4 905 911 10.1038/sj.bjp.0704326 1:CAS:528:DC%2BD3MXotlChtro%3D 11606332
19. M Muscará F Lovren W McKnight, et al. 2001 Vasorelaxant effects of a nitric oxide-releasing aspirin derivative in normotensive and hypertensive rats Br J Pharmacol 133 8 1314 1322 10.1038/sj.bjp.0704209 11498517
20. Y Nagakura M Okada A Kohara, et al. 2003 Allodynia and hyperalgesia in adjuvant-induced arthritic rats: time course of progression and efficacy of analgesics J Pharmacol Exp Ther 306 2 490 497 10.1124/jpet.103.050781 1:CAS:528:DC%2BD3sXlslGltLg%3D 12730275 (Pubitemid 36886145)
21. KV Nemmani SV Mali N Borhade, et al. 2009 NO-NSAIDs: Gastric-sparing nitric oxide-releasable prodrugs of non-steroidal anti-inflammatory drugs Bioorg Med Chem Lett 19 18 5297 5301 10.1016/j.bmcl.2009.07.142 1:CAS:528: DC%2BD1MXhtVeqsLzP 19683923
22. S Peng A Duggan 2005 Gastrointestinal adverse effects of non-steroidal anti-inflammatory drugs Expert Opin Drug Saf 4 2 157 169 10.1517/14740338.4.2. 157 1:CAS:528:DC%2BD2MXls1ehsLc%3D 15794710 (Pubitemid 40867330)
23. P Queneau 2001 The saga of aspirin: centuries-old ancestors of an old lady who doesn't deserve to die Therapie 56 6 723 726 1:STN:280: DC%2BD387ksVWlsw%3D%3D 11878097
24. KB Reuter JL Wallace 1999 Phosphodiesterase inhibitors prevent NSAID enteropathy independently of effects on TNF-alpha release Am J Physiol Gastrointest Liver Physiol 277 G847 G854 1:CAS:528:DyaK1MXntFCjur4%3D
25. N Reynaert K Ckless S Korn, et al. 2004 Nitric oxide represses inhibitory kappaB kinase through S-nitrosylation Proc Natl Acad Sci USA 101 24 8945 8950 10.1073/pnas.0400588101 1:CAS:528:DC%2BD2cXltlWqsrc%3D 15184672 (Pubitemid 38781591)
26. J Scheiman 1996 NSAIDs, gastrointestinal injury, and cytoprotection Gastroenterol Clin North Am 25 2 279 298 10.1016/S0889-8553(05)70247-8 1:STN:280:DyaK2s%2FhtlChug%3D%3D 9229573 (Pubitemid 26161469)
27. K Takeuchi H Ukawa A Konaka, et al. 1998 Effect of nitric oxide-releasing aspirin derivative on gastric functional and ulcerogenic responses in rats: comparison with plain aspirin J Pharmacol Exp Ther 286 1 115 121 1:CAS:528:DyaK1cXksFChurw%3D 9655849
28. Vogel H (2002) Drug discovery and evaluation: pharmacological assays, 2nd edn. Springer, New York
29. J Wallace L Vong 2008 NSAID-induced gastrointestinal damage and the design of GI-sparing NSAIDs Curr Opin Investig Drugs 9 11 1151 1156 1:CAS:528:DC%2BD1cXhsVOku7bN 18951293
30. J Wallace S Viappiani M Bolla 2009 Cyclooxygenase-inhibiting nitric oxide donators for osteoarthritis Trends Pharmacol Sci 30 3 112 117 10.1016/j.tips.2009.01.001 1:CAS:528:DC%2BD1MXivVGgtbk%3D 19230986
31. B Whittle 2005 Nitric oxide-modulating agents for gastrointestinal disorders Expert Opin Investig Drugs 14 11 1347 1358 10.1517/13543784.14.11.1347 1:CAS:528:DC%2BD2MXhtFGqsrjL 16255675 (Pubitemid 41601451)
32. Xing Z, Jordana M, Kirpalani H et al (1994) Cytokine expression by neutrophils and macrophages in vivo: endotoxin induces tumor necrosis factor-alpha, macrophage inflammatory protein-2, interleukin-1 beta, and interleukin-6 but not RANTES or transforming growth factor-beta 1 mRNA expression in acute lung inflammation. Am J Respir Cell Mol Biol 10(2):148-153
33. D Young E Cochran V Dhawan, et al. 2005 A comparison of the cyclooxygenase inhibitor-NO donors (CINOD), NMI-1182 and AZD3582, using in vitro biochemical and pharmacological methods Biochem Pharmacol 70 9 1343 1351 10.1016/j.bcp.2005.08.004 1:CAS:528:DC%2BD2MXhtVKjs7bM 16168964 (Pubitemid 41383470)