Galactosyl prodrug of ketorolac: Synthesis, stability, and pharmacological and pharmacokinetic evaluations

Journal of Medicinal Chemistry

Volumn 52, Issue 12, 2009, Pages 3794-3800

  Curcio, Annalisa ^a   Sasso, Oscar ^a   Melisi, Daniela ^a   Nieddu, Maria ^b   La Rana, Giovanna ^a   Russo, Roberto ^a   Gavini, Elisabetta ^b   Boatto, Gianpiero ^b   Abignente, Enrico ^a   Calignano, Antonio ^a   Rimoli, Maria Grazia ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; GALACTOSE; KETOGAL; KETOROLAC; MAGNESIUM SULFATE; PRODRUG; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CONJUGATION; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG CONJUGATION; DRUG DOSE COMPARISON; DRUG HALF LIFE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TISSUE LEVEL; MALE; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; PAW EDEMA; TIME TO MAXIMUM PLASMA CONCENTRATION; ULCEROGENESIS; VISCERAL PAIN; WRITHING TEST;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DOSE-RESPONSE RELATIONSHIP, DRUG; EDEMA; GALACTOSE; HYDROGEN-ION CONCENTRATION; KETOROLAC; MICE; MOLECULAR CONFORMATION; PAIN; PRODRUGS; STOMACH ULCER; TIME FACTORS;

EID: 67549137414     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900051r     Document Type: Article

References (27)

1. Gillis, J. C.; Brogden, R. N. Ketorolac. A reappraisal of its pharmacodynamic and pharmacokinetic properties and therapeutic use in pain management. Drugs 1997, 53 (1), 139-188. (Pubitemid 27045700)
2. Laporte, J. R.; Ibáñez, L.; Vidal, X.; Vendrell, L.; Leone, R. Upper gastrointestinal bleeding associated with the use of NSAIDs: newer versus older agents. Drug Safety 2004, 27 (6), 411-420. (Pubitemid 38608459)
3. Dula, D. J.; Anderson, R.; Wood, G. C. A prospective study comparing i.m. ketorolac with i.m. meperidine in the treatment of acute biliary colic. J. Emerg. Med. 2000, 20, 121-124.
4. Cioli, V.; Putzolu, S.; Rossi, V.; Barcellona, P. S.; Corradino, C. The role of direct tissue contact in the production of gastro-intestinal ulcers by anti-inflammatory drugs in rats. Toxicol. Appl. Pharmacol. 1979, 50, 283-289.
5. Rainsford, K. D. Mechanisms of gastrointestinal toxicity of nonsteoridal anti-inflammatory drugs. Scand. J. Gastroenterol., Suppl. 1989, 163, 9-16. (Pubitemid 19218914)
6. Hawkey, C.; Laine, L.; Simon, T.; Beaulieu, A.; Maldonado-Cocco, J.; Acevedo, E.; Shahane, A.; Quan, H.; Bolognese, J.; Mortensen, E. Comparison of the effect of rofecoxib (a cyclooxygenase 2 inhibitor), ibuprofen and placebo on the gastroduodenal mucosa of patients with osteoarthritis: a randomized, double blind, placebo-controlled trial. Arthritis Rheum. 2000, 43 (2), 370-377. (Pubitemid 30395746)
7. Stanczak, A.; Ferra, A. Prodrugs and soft drugs. Pharmacol. Rep. 2006, 58, 599-613.
8. Mishra, A.; Veerasamy, R.; Jain, P. K.; Dixit, V. K.; Agrawal, R. K. Synthesis, characterization and pharmacological evaluation of amide prodrugs of ketorolac. Eur. J. Med. Chem. 2008, 43 (11), 2464-2472.
9. Vyas, S.; Trivedi, P.; Chaturvedi, S. C. Ketorolac-dextran conjugates: synthesis, in vitro and in vivo evaluation. Acta Pharm. 2007, 57, 441-450.
10. Rainsford, K. D.; Whitehouse, M. W. Protection of the Gastric Mucosal Lining from Damage by Aspirin and Related Drugs. US 4440762. 1984.
11. Kauffman, G. L., Jr. Gastric mucus and bicarbonate secretion in relation to mucosal protection. J. Clin. Gastroenterol. 1981, 3 (2), 45-50.
12. Srikanta, B. M.; Siddaraju, M. N.; Dharmesh, S. M. A novel phenol-bound pectic polysaccharide from Decalepis hamiltonii with multistep ulcer preventive activity. World J. Gastroenterol. 2007, 13 (39), 5196-5207.
13. Bonina, F.; Puglia, C.; Rimoli, M. G.; Melisi, D.; Boatto, G.; Nieddu, M.; Calignano, A.; La Rana, G.; De Caprariis, P. Glycosyl derivatives of dopamine and L-dopa as anti-Parkinson prodrugs: synthesis, pharmacological activity and in vitro stability studies. J. Drug Targeting 2003, 11, 25-36. (Pubitemid 36527393)
14. Melisi, D.; Secondo, A.; Montoro, P.; Piacente, S.; Rimoli, M. G.; Minale, M.; de Caprariis, P.; Annunziato, L. Galactosyl derivatives of L-arginine and D-arginine: synthesis, stability, cell permeation, and nitric oxide production in pituitary GH3 cells. J. Med. Chem. 2006, 49 (16), 4826-4833.
15. Ruocco, L. A.; Viggiano, D.; Viggiano, A.; Abignente, E.; Rimoli, M. G.; Melisi, D.; Curcio, A.; Nieddu, M.; Boatto, G.; Carboni, E.; Carnevale, U. A.; Sadile, A. G. Galactosylated dopamine enters into the brain, blocks the mesocorticolimbic system and modulates activity and scanning time in Naples high excitability rats. Neuroscience 2008, 152 (1), 234-244.
16. Ruocco, L. A.; Viggiano, D.; Pignatelli, M.; Iannaccone, T.; Rimoli, M. G.; Melisi, D.; Curcio, A.; De Lucia, S.; Carboni, E.; Carnevale, U. A.; de Caprariis, P.; Sadile, A. G. Galactosilated dopamine increases attention without reducing activity in C57BL/6 mice. Behav. Brain Res. 2008, 187 (2), 449-454.
17. Posadas, I.; Bucci, M.; Roviezzo, F.; Rossi, A.; Parente, L.; Sautebin, L.; Cirino, G. Carrageenan-induced mouse paw oedema is biphasic, age-weight dependent and displays differential nitric oxide cyclooxygenase-2 expression. Br. J. Pharmacol. 2004, 142 (2), 331-338.
18. Qandil, A.; Al-Nabulsi, S.; Al-Taani, B.; Tashtoush, B. Synthesis of piperazinylalkyl ester prodrugs of ketorolac and their in vitro evaluation for transdermal delivery. Drug Dev. Ind. Pharm. 2008, 34 (10), 1054-1063.
19. Bhandari, K. H.; Newa, M.; Yoon, S. I.; Kim, J. S.; Jang, K. Y.; Kim, J. A.; Yoo, B. K.; Woo, J. S.; Lee, J. H.; Kim, D. D.; Choi, H. G.; Yong, C. S. Evaluation of physicochemical properties, skin permeation and accumulation profiles of ketorolac fatty ester prodrugs. Biol. Pharm. Bull. 2007, 30 (11), 2211-2216.
20. Puglia, C.; Filosa, R.; Peduto, A.; de Caprariis, P.; Boatto, G.; Nieddu, M.; Santagati, N. A.; Bonina, F. Synthesis, physicochemical properties and in vitro permeation studies of new ketorolac ester derivatives. Curr. Drug Delivery 2007, 4 (3), 205-210. (Pubitemid 47025404)
21. Zimmermann, M. Ethical guidelines for investigations of experimental pain in conscious animals. Pain 1983, 16, 109-110.
22. Jain, N. K.; Kulkarni, S. K.; Singh, A. Differential antinociceptive effect of cyclooxygenase inhibitors in acetic acid-induced chemonociception in mice. Analgesia 2001, 5, 211-216.
23. Calignano, A.; La Rana, G.; Piomelli, D. Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide. Eur. J. Pharmacol. 2001, 419, 191-198.
24. D'Agostino, G.; La Rana, G.; Russo, R.; Sasso, O.; Iacono, A.; Esposito, E.; Raso, G. M.; Cuzzocrea, S.; Lo Verme, J.; Piomelli, D.; Meli, R.; Calignano, A. Acute intracerebroventricular administration of palmitoylethanolamide, an endogenous peroxisome proliferator-activated receptor-alpha agonist, modulates carrageenan-induced paw edema in mice. J. Pharmacol. Exp. Ther. 20073, 1137-1143.
25. Chan, C. C.; Boyce, S.; Brideau, C.; Ford-Hutchinson, A. W.; Gordon, R.; Guay, D.; Hill, R. G.; Li, C. S.; Mancini, J.; Penneton, M.; Praist, P.; Rasori, R.; Riendeau, D.; Roy, P.; Tagari, P.; Vickers, P.; Wong, E.; Rodger, I. W. Pharmacology of a selective cyclooxygenase-2 inhibitor, L-745,337: a novel nonsteroidal anti-inflammatory agent with an ulcerogenic sparing effect in rat and nonhuman primate stomach. J. Pharmacol. Exp. Ther. 1995, 3, 1531-1537.
26. Peters, F. T.; Maurer, H. H. Bioanalytical method validation and its implications for forensic and clinical toxicology. Accredit. Qual. Assur. 2002, 7, 441-449.
27. Taverniers, I.; de Loose, M.; Van Bockstaele, E. Analytical method validation and quality assurance. Trends Anal. Chem. 2004, 23, 533-551.