Chirality and nonsteroidal anti-inflammatory drugs

Drugs

Volumn 52, Issue SUPPL. 5, 1996, Pages 47-58

  Hayball, Peter J ^a,b  

^a REPATRIATION GENERAL HOSPITAL   (Australia)

^b UNIVERSITY OF SOUTH AUSTRALIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLPROPIONIC ACID DERIVATIVE; CARPROFEN; FENOPROFEN; IBUPROFEN; INDOPROFEN; KETOPROFEN; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN SYNTHASE; THROMBOXANE;

CHIRALITY; CONFERENCE PAPER; DRUG POTENCY; DRUG SELECTIVITY; ENANTIOMER; ENZYME INHIBITION; HUMAN; NONHUMAN; STEREOCHEMISTRY; THROMBOCYTE AGGREGATION INHIBITION;

EID: 0029959195     PISSN: 00126667     EISSN: None     Source Type: Journal    
DOI: 10.2165/00003495-199600525-00006     Document Type: Conference Paper

References (87)

1. Vane JR. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nature 1971; 231: 232-5
2. Takeguchi C, Sih CJ. A rapid spectrophotometric assay for prostaglandin synthetase: application to the study of non-steroidal anti-inflammatory agents. Prostaglandins 1972; 2: 169-84
3. Lewis AJ, Furst DE. Non-steroidal anti-inflammatory drugs: mechanisms and clinical uses. 2nd ed. New York: Marcel Dekker, 1994: 1-2
4. Vane JR, Botting RM. The mode of action of anti-inflammatory drugs. Postgrad Med J 1990; 66 Suppl. 4: S2-17
5. Cashman J, McAnulty G. Nonsteroidal anti-inflammatory drugs in perisurgical pain management. Drugs 1995; 49: 51-70
6. Evans AM. Enantioselective pharmacodynamics and pharmacokinetics of chiral non-steroidal anti-inflammatory drugs. Eur J Clin Pharmacol 1992; 42: 237-56
7. Hutt AJ, Caldwell J. The metabolic chiral inversion of 2-arylpropionic acids - a novel route with pharmacological consequences. J Pharm Pharmacol 1983; 35: 693-704
8. Williams KM. Enantiomers in arthritic disorders. Pharmacol Ther 1990; 46: 273-95
9. Gaut ZN, Baruth H, Randall LO, et al. Stereoisomeric relationships among anti-inflammatory activity, inhibition of platelet aggregation, and inhibition of prostaglandin synthetase. Prostaglandins 1975; 10: 59-66
10. Rubin A, Knadler MP, Ho PPK, et al. Stereoselective inversion of (R)-fenoprofen to (S)-fenoprofen in humans. J Pharm Sci 1985; 74: 82-4
11. Evans AM, Nation RL, Sansom LN, et al. Effect of racemic ibuprofen dose on the magnitude and duration of platelet cyclo-oxygenase inhibition: relationship between inhibition of thromboxane production and the plasma unbound concentration of S(+)-ibuprofen. Br J Clin Pharmacol 1991; 31: 131-8
12. Cerletti C, Manarini S, Colombo M, et al. The (+)-enantiomer is responsible for the antiplatelet and anti-inflammatory activity of (±)-indobufen. J Pharm Pharmacol 1990; 42: 885-7
13. Hayball PJ, Nation RL, Bochner F. Enantioselective pharmacodynamics of the nonsteroidal antiinflammatory drug ketoprofen: in vitro inhibition of human platelet cyclooxygenase activity. Chirality 1992; 4: 484-7
14. Suesa N, Fernandez MR, Gutierrez M, et al. Stereoselective cyclooxygenase inhibition in cellular models by the enantiomers of ketoprofen. Chirality 1993; 5: 589-95
15. Williams KM. Chiral NSAIDs: so what? Agents Actions Suppl 1993; 44: 15-22
16. Hayball PJ, Nation RL, Bochner F, et al. The influence of renal function on the enantioselective pharmacokinetics and pharmacodynamics of ketoprofen in patients with rheumatoid arthritis. Br J Clin Pharmacol 1993; 36: 185-93
17. Vane JR. Towards a better aspirin. Nature 1994; 367: 215-6
18. Dray A, Bevan S. Inflammation and hyperalgesia: the team effort. Trends Pharm Sci 1993; 14: 287-90
19. Aslanian R, Carruthers NI, Kaminski JJ. Cyclo-oxygenase-2: a novel target for therapeutic intervention. Exp Opin Invest Drugs 1994; 3: 1323-5
20. Hayllar J, Bjarnason I. NSAIDs, COX-2 inhibitors, and the gut. Lancet 1995; 346: 521-2
21. Somasundaram S, Hayllar H, Rafi S, et al. The biochemical basis of non-steroidal anti-inflammatory drug-induced damage to the gastrointestinal tract: a review and a hypothesis. Scand J Gastroenterol 1995; 30: 289-99
22. Meade EA, Smith WL, DeWitt DL. Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other nonsteroidal anti-inflammatory drugs. J Biol Chem 1993; 268: 6610-14
23. Cipollone F, Ganci A, Panara MR, et al. Effects of nabumetone on prostanoid biosynthesis in humans. Clin Pharmacol Ther 1995; 58: 335-41
24. Patrignani P, Panara MR, Greco A, et al. Biochemical and pharmacological characterization of the cyclooxygenase activity of human blood prostaglandin endoperoxide synthases. J Pharmacol Exp Ther 1994; 271: 1705-12
25. Panara MR, Greco A, Santini G, et al. Effects of the novel anti-inflammatory compounds, N-[2-(cyclohexyloxy)-4-nitrophenyl] methanesuphonamide(NS-398)and 5-methanesulphonamido-6-(2,4-difluorothiophenyl)-1-indanone (L-745,337), on the cyclo-oxygenase activity of human blood prostaglandin endoperoxide synthases. Br J Pharmacol 1995; 116: 2429-34
26. Matsuda K, Tanaka Y, Ushiyama S, et al. Inhibition of prostaglandin synthesis by sodium 2-[4-(2-oxocyclopentylmethyl) phenyl]-propionate dihydrate (CS-600), a new anti-inflammatory drug, and its active metabolite in vitro and in vivo. Biochem Pharmacol 1984; 15: 2473-8
27. Ferreira SH, Vane JR. Mode of action of anti-inflammatory agents which are prostaglandin synthetase inhibitors. In: Vane JR, Ferreira SH, editors. Anti-inflammatory drugs. Berlin: Springer, 1979
28. Tomlinson RV, Ringold HJ, Qureshi MC, et al. Relationship between inhibition of prostaglandin synthesis and drug efficacy: support for the current theory on mode of action of aspirin-like drugs. Biochem Biophys Res Commun 1972; 46: 552-8
29. Abramson SB, Weissmann G. The mechanism of action of non-steroidal antiinflammatory drugs. Arthritis Rheum 1989; 32: 1-9
30. Day RO, Graham GG, Williams KM, et al. Clinical pharmacology of non-steroidal anti-inflammatory drugs. Pharmacol Ther 1987; 33: 383-433
31. Goodwin JS. Mechanism of action of nonsteroidal anti-inflammatory drugs. Am J Med 1984; 77 Suppl. 1A: 57-64
32. Brune K, Beck WS, Geisslinger G, et al. Aspirin-like drugs may block pain independently of prostaglandin synthesis inhibition. Experientia 1991; 47: 257-60
33. Brune K, Rainsford KD, Wagner K, et al. Inhibition by anti-inflammatory drugs of prostaglandin production in cultured macrophages. Factors influencing the apparent drug effects. Naunyn-Schmiedebergs Arch Pharmacol 1981; 315: 269-76
34. Rosenkranz B, Fisher C, Meese CO, et al. Effects of salicylic and acetylsalicylic acid alone and in combination on platelet aggregation and prostanoid synthesis in man. Br J Clin Pharmacol 1986; 21: 309-17
35. Brandt KD, Palmoski MJ. Effects of salicylates and other non-steroidal anti-inflammatory drugs on articular cartilage. Am J Med 1984; 77 Suppl. 1A: 65-9
36. Shelly J, Hoff SF. Effects of non-steroidal anti-inflammatory drugs on isolated human polymorphonuclear leukocytes (PMN): chemotaxis, superoxide production, degranulation and N-formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP) receptor binding. Gen Pharmacol 1989; 20: 329-34
37. Rampart M, Williams TJ. Suppression of inflammatory oedema by ibuprofen involving a mechanism independent of cyclooxygenase inhibition. Biochem Pharmacol 1986; 35: 581-6
38. Freneaux E, Fromenty B, Berson A, et al. Stereoseleclive and nonstereoselective effects of ibuprofen enantiomers on mitochondrial ß-oxidation of fatty acids. J Pharmacol Exp Ther 1990; 255: 529-35
39. Geneve J, Hayat-Bonan B, Labbe G, et al. Inhibition of mitochondrial β-oxidation of fatty acids by pirprofen. Role in microvesicular steatosis due to this nonsteroidal anti-inflammatory drug. J Pharmacol Exp Ther 1987; 242: 1133-7
40. Zhao B, Geisslinger G, Hall I, et al. The effect of the enantiomers of ibuprofen and flurbiprofen on the β-oxidation of palmitate in the rat. Chirality 1992; 4: 137-41
41. Twomey BM, Dale MM. Cyclooxygenase-independent effects of non-steroidal anti-inflammatory drugs on the neutrophil respiratory burst. Biochem Pharmacol 1992; 43: 413-8
42. Kawai K, Shiojiri H, Fukushima H, et al. The effect of clindanac, a potent anti-inflammatory drug, on mitochondrial respiration: a consideration of the uncoupling activity of optical enantiomers. Res Commun Chem Pathol Pharmacol 1984; 45: 399-406
43. Villanueva M, Heckenberger R, Strobach H, et al. Equipotent inhibition by R(-)-ibuprofen, S(+)-ibuprofen and racemic ibuproten of human polymorphonuclear cell function in vitro. Br J Clin Pharmacol 1993; 35: 235-42
44. Jamali F, Mehvar R, Pasutto FM. Enantioselective aspects of drug action and disposition: therapeutic pitfalls. J Pharm Sci 1989; 78: 695-715
45. Lee EJD, Williams KM. Chirality: clinical pharmacokinetic and pharmacodynamic considerations. Clin Pharmacokinet 1990; 18: 339-45
46. Tucker GT, Lennard MS. Enantiomer specific pharmacokinetics. Pharmacol Ther 1990; 45: 309-29
47. Ariens EJ. Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. Eur J Clin Pharmacol 1984; 26: 663-8
48. Evans AM, Nation RL, Sansom LN, et al. Stereoselective drug disposition: potential for misinterpretation of drug disposition data. Br J Clin Pharmacol 1988; 26: 771-80
49. Jamali F, Mehvar R, Lemko C, et al. Application of a stereospecific high-performance liquid chromatographic assay to a pharmacokinetic study of etodolac enantiomers in humans. J Pharm Sci 1988; 77: 963-6
50. Hayball PJ, Wrobel J, Tamblyn JG, et al. The pharmacokinetics of ketorolac enantiomers following intramuscular administration of the racemate. Br J Clin Pharmacol 1994; 37: 75-8
51. Guzman A, Yuste F, Toscano RA, et al. Absolute configuration of (-)-5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2a]pyrrole-1-carboxylic acid. J Med Chem 1986; 29: 589-91
52. Caldwell J, Winter SM, Hutt AJ. The pharmacological and toxicological significance of the stereochemistry of drug disposition. Xenobiotica 1988; 18 Suppl. 1: 59-70
53. Eichelbaum M. Pharmacokinetic and pharmacodynamic consequences of stereoselective drug metabolism in man. Biochem Pharmacol 1988; 37: 93-6
54. Testa B. Substrate and product stereoselectivity in monooxygenase-mediated drug activation and inactivation. Biochem Pharmacol 1988; 37: 85-92
55. Evans AM, Nation RL, Sansom LN, et al. Stereoselective plasma protein binding of ibuprofen enantiomers. Eur J Clin Pharmacol 1989; 36: 283-90
56. Hayball PJ, Holman JW, Nation RL, et al. Marked enantioselective protein binding of ketorolac in vitro: elucidation of enantiomer unbound tractions following facile synthesis and direct chiral HPLC resolution of tritium-labelled ketorolac. Chirality 1994; 6: 642-8
57. Jamali F, Russell AS, Foster RT, et al. Ketoprofen pharmacokinetics in humans: evidence of enantiomeric inversion and lack of interaction. J Pharm Sci 1990; 79: 460-1
58. Caldwell J. Stereochemical determinants of the nature and consequences of drug metabolism. J Chromatogr A 1995; 694: 39-48
59. Shirley MA, Guan X, Kaiser DG, et al. Taurine conjugation of ibuprofen in humans and in rat liver in vitro. Relationship to metabolic chiral inversion. J Pharmacol Exp Ther 1994; 269: 1166-75
60. Tanaka Y, Shimomura Y, Hirota T, et al. Formation of glycine conjugate and (-)-(R)-enantiomer from(+)-(S)-2-phenylpropionic acid suggesting the formation of the CoA thioester intermediate of (+)-(S)-enantiomer in dogs. Chirality 1992; 4: 342-8
61. Upton RA, Buskin JN, Williams RL, et al. Negligible excretion of unchanged ketoprofen, naproxen and probenecid in urine. J Pharm Sci 1980; 69: 1254-7
62. Mroszczak E, Lee FW, Combs D, et al. Ketorolac tromethainine absorption, distribution, metabolism, excretion, and pharmacokinetics in animals and humans. Drug Metab Dispos 1987; 15: 618-26
63. 14C-ximoprofen in rats, baboons and humans. Xenobiotica 1990; 20: 233-46
64. Spahn-Langguth H, Benet LZ. Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metah Rev 1992; 24: 5-48
65. Advenier C, Roux A, Gobert C, et al. Pharmacokinetics of ketoprofen in the elderly. Br J Clin Pharmacol 1983; 16: 65-70
66. Anttila M, Haataja M, Kasanan A. Pharmacokinetics of naproxen in subjects with normal and impaired renal function. Eur J Clin Pharmacol 1980; 18: 263-8
67. Foster RT, Jamali F, Russell AS. Pharmacokinetics of ketoprofen enantiomers in cholecystectomy patients: influence of probenecid. Eur J Clin Pharmacol 1989; 37: 589-94
68. Meffin PJ, Sallustio BC, Purdie YJ, et al. Enantioselective disposition of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs. I. 2-Phenylpropionic acid disposition. J Pharmacol Exp Ther 1986; 238: 280-7
69. Hayball PJ. Formation and reactivity of acyl glucuronides: the influence of chirality. Chirality 1995; 7: 1-9
70. Peskar BM, Kluge S, Peskar BA, et al. Effects of pure enantiomers of flurbiprofen in comparison to racemic flurbiprofen on eicosanoid release from various rat organs ex vivo. Prostaglandins 1991; 42: 515-31
71. Wechter WJ, Bigornia AE, Murray ED, et al. Rac-flurbiprofen is more ulcerogenic than its (S)-enantiomer. Chirality 1993; 5: 492-4
72. Wallace JL, Granger DN. Pathogenesis of NSAID gastropathy: are neutrophils the culprits? Trends Pharm Sci 1992; 13: 129-31
73. Carson JL, Willett LR. Toxicity of nonsteroidal anti-inflammatory drugs. An overview of epidemiological evidence. Drugs 1993; 46Suppl. 1: 243-8
74. Willett LR, Carson JL, Strom BL. Epidemiology ot gastrointestinal damage associated with nonsteroidal anti-inflammatory drugs. Drug Saf 1994; 10: 170-81
75. Rainsford KD. Inhibitors of eicosanoid metabolism. In: Curtis-Prior PB, editor. Prostaglandins - biology and chemistry of prostaglandins and related eicosanoids. Edinburgh: Churchill Livingstone, 1988: 52-68
76. Kubota T, Komatsu H, Kawamoto H, et al. Studies on the effects of anti-inflammatory action of benzoyl-hydratropic acid (ketoprofen) and other drugs, with special reference to proslaglandin synthesis. Arch Int Pharmacodyn Ther 1979; 237: 169-76
77. Fears R, Richards DH. Association between lipid-lowering activity of aryl-substituted carboxylic acids and formation of substituted glycerolipids in rats. Biochem Soc Trans 1981; 9: 572-3
78. Caldwell J, Marsh MV. Interrelationship between xenobiotic metabolism and lipid biosynthesis. Biochem Pharmacol 1983; 32: 1667-72
79. Williams KM, Day RO. The contribution of enantiomers to variability in response to anti-inflammatory drugs. Agents Actions Suppl 1988; 24: 76-84
80. Benet LZ, Spahn-Langguth H, Iwakawa S, et al. Predictability of the covalent binding of acidic drugs in man. Life Sci 1993; 53: PL141-6
81. Ding A, Ojingwa JC, McDonagh AF, et al. Evidence for covalent binding of acyl glucuronides to serum albumin via an imine mechanism as revealed by tandem mass spectrometry. Proc Natl Acad Sci USA 1993; 90: 3797-801
82. Yvon M, Wal J-M. Identification of lysine residue 199 of human serum albumin as a binding site for benzylpenicilloyl groups. FEBS Lett 1988; 239: 237-40
83. Smith PC, McDonagh AF, Benet LZ. Irreversible binding of zomepirac to plasma protein in vitro and in vivo. J Clin Invest 1986; 77: 934-9
84. Simkin PA. Concentration-effect relationships of NSAID. J Rheumatol 1988; 15 Suppl. 17: 40-3
85. Geisslinger G, Stock KP, Loew D, et al. Variability in the stereoselective disposition of ibuprofen in patients with rheumatoid arthritis. Br J Clin Pharmacol 1993; 35: 603-7
86. Birkett DJ. Racemates of enantiomers: regulatory approaches. Clin Exp Pharmacol Physiol 1989; 16: 479-83
87. Lennard MS. Clinical pharmacology through the looking glass: reflections on the racemate vs enantiomer debate. Br J Clin Pharmacol 1991; 31: 623-5