Design, synthesis, and pharmacological activity of nonallergenic pyrazolone-type antipyretic analgesics

Journal of Medicinal Chemistry

Volumn 53, Issue 24, 2010, Pages 8727-8733

  Uramaru, Naoto ^a,b   Shigematsu, Hidenari ^b   Toda, Akihisa ^c   Eyanagi, Reiko ^c   Kitamura, Shigeyuki ^b   Ohta, Shigeru ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b NIHON PHARMACEUTICAL UNIVERSITY   (Japan)

^c DAIICHI UNIVERSITY OF PHARMACY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (1,1 DIMETHYLETHYL) 5 METHYL 2 PHENYL 1,2 DIHYDRO 3H PYRAZOL 3 ONE; 5 METHYL 1,2 DIPHENYL 1,2 DIHYDRO 3H PYRAZOL 3 ONE; 5 METHYL 2 PHENYL 1 (2,2,2 TRIFLUOROETHYL) 1,2 DIHYDRO 3H PYRAZOL 3 ONE; ANTIPYRETIC ANALGESIC AGENT; DRUG METABOLITE; INDOMETACIN; MEFENAMIC ACID; METHYL GROUP; NORPHENAZONE; PHENAZONE; PYRAZOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ALLERGENICITY; ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIPYRETIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DEALKYLATION; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; FEVER; GUINEA PIG; HYPERALGESIA; IN VIVO STUDY; NOCICEPTION; NONHUMAN; PAIN THRESHOLD; RAT; SKIN MANIFESTATION; STRUCTURE ACTIVITY RELATION;

ALLERGENS; ANALGESICS; ANIMALS; ANTIPYRETICS; BODY TEMPERATURE; DRUG DESIGN; FEVER; GUINEA PIGS; HYPERALGESIA; HYPERSENSITIVITY, DELAYED; INTERLEUKIN-1BETA; MALE; MICROSOMES, LIVER; PYRAZOLONES; RATS; RATS, SPRAGUE-DAWLEY; SKIN TESTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78650316630     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101208x     Document Type: Article

References (30)

1. Knorr, L. Einwirk von acetessigester auf phenylhydrazin Ber. Dtsch. Chem. Ges. 1883, 16, 2597-2599
2. Beaver, W. T. Mild analgesics. A review of their clinical pharmacology Am. J. Med. Sci. 1965, 250, 577-604
3. Brogden, R. N. Pyrazolone derivatives Drugs 1986, 32, 60-70
4. Volz, M.; Kellner, H. M. Kinetics and metabolism of pyrazolones (propylphenazone, aminopyrine and dipyrone) Br. J. Clin. Pharmacol. 1980, 10, 299S-308S
5. Levy, M. Hypersensitivity to pyrazolones Thorax 2000, 55, S72-S74
6. Voigtlander, V. Adverse dermatological reactions to pyrazolone Agents Acti. Suppl. 1986, 19, 303-311
7. Pisciotta, A. V. Drug-induced agranulocytosis. Peripheral destruction of polymorphonuclear leucocytes and their marrow precursors Blood Rev. 1990, 4, 226-237
8. Agúndez, J. A.; Martínez, C.; Benítez, J. Metabolism of aminopyrine and derivatives in man: in vivo study of monomorphic and polymorphic metabolic pathways Xenobiotica 1995, 25, 417-427
9. Bottcher, J.; Bassmann, H.; Schuppel, R. Quantitation of norantipyrine sulphate and norantipyrine glucuronide as major metabolites of antipyrine in man and rat J. Pharm. Pharmacol. 1984, 36, 391-398
10. Bottcher, J.; Bassmann, H.; Schuppel, R. Quantitation and urinary pattern of 4,4′-dihydroxyantipyrine, 4-hydroxyantipyrine and 3- hydroxymethylantipyrine, as main metabolites of antipyrine in man and rat J. Pharm. Pharmacol. 1982, 34, 168-175
11. Yoshimura, H.; Shimeno, H.; Tsukamoto, H. Metabolism of drugs-LIX. A new metabolite of antipyrine Biochem. Pharmacol. 1968, 17, 1511-1516
12. Yoshimura, H.; Shimeno, H.; Tsukamoto, H. Metabolism of Drugs. LXX. Further study on antipyrine metabolism Chem. Pharm. Bull. 1971, 19, 41-45
13. Shigematsu, H.; Hisanari, Y.; Yoshida, K.; Shimeno, H. Delayed allergic reactions with aminopyrine metabolites Skin Res. 1988, 30, 95-100
14. Shigematsu, H.; Hisanari, Y.; Eyanagi, R.; Toshitani, S. Sensitization and elicitation of delayed allergic skin reaction with antipyrine metabolite Jpn. J.Dermatoallergol. 1994, 1, 278-287
15. Kato, T.; Sato, M.; Tabei, K.; Kawashima, E. Studies on ketene and its derivatives. LXIX. Reaction of diketene with hydrazobenzenes Chem. Pharm. Bull. 1975, 23, 456-459
16. Hertl, M.; Merk, H. F. Lymphocyte activation in cutaneous drug reactions J. Invest. Dermatol. 1995, 105, 95S-98S
17. Weltzien, H. U.; Padovan, E. Molecular features of penicillin allergy J. Invest. Dermatol. 1998, 110, 203-206
18. Park, B. K.; Kitteringham, N. R.; Powell, H.; Pirmohamed, M. Advances in molecular toxicology - towards understanding idiosyncratic drug toxicity Toxicology 2000, 153, 39-60
19. Park, B. K.; Pirmohamed, M.; Kitteringham, N. R. The role of cytochrome P450 enzymes in hepatic, extrahepatic human drug toxicity Pharmacol. Ther. 1995, 68, 385-424
20. Himly, M.; Jahn-Schmid, B.; Pittertschatscher, K.; Bohle, B.; Grubmayr, K.; Ferreira, F.; Ebner, H.; Ebner, C. IgE-mediated immediate-type hypersensitivity to the pyrazolone drug propylphenazone J. Allergy Clin. Immunol. 2003, 111, 882-888
21. Shimeno, H.; Yoshimura, H. Metabolism of drugs. LXXVII. In vitro metabolism of antipyrine Yakugaku Zassi 1972, 92, 1376-1379
22. Mikati, M. A.; Szabo, G. K.; Pylilo, R. J.; LeDuc, B. W.; Browne, T. R.; Greenblatt, D. J. Improved high-performance liquid chromatographic assay of antipyrine, hydroxymethylantipyrine, 4-hydroxyantipyrine and norantipyrine in urine J. Chromatogr. 1988, 433, 305-311
23. Kihara, T.; Toda, A.; Umesue, I.; Ono, N.; Shigematsu, H.; Soeda, S.; Shimeno, H. Effect of interleukin 1β-induced fever on hepatic drug metabolism in rat Xenobiotica 1998, 28, 559-569
24. Randall, L. O.; Selltto, J. J. A method for measurement of analgesic activity on inflamed tissue Arch. Int. Pharmacodyn. Ther. 1957, 111, 409-419
25. Oh-ishi, S.; Hayashi, I.; Utsunomiya, I.; Hayashi, M.; Yamaki, K.; Yamasu, A.; Nakano, T. Roles of kallikrein-kinin system in acute inflammation: studies on high- and low-molecular-weight kininogens-deficient rats (B/N-Katholiek strain) Agents Act. 1987, 21, 384-386
26. Eyanagi, R.; Toda, A.; Ishii, Y.; Saito, H.; Soeda, S.; Shimeno, H.; Shigematsu, H. Antigenicity of sulfanilamide and its metabolites using fluorescent-labelled compounds Xenobiotica 2005, 35, 911-925
27. Kohno, Y.; Kitamura, S.; Sanoh, S; Sugihara, K.; Fujimoto, N.; Ohta, S. Metabolism of the α,β-unsaturated ketones, chalcone and trans -4-phenyl-3-buten-2-one, by rat liver microsomes and estrogenic activity of the metabolites Drug Metab. Dispos. 2005, 33, 1115-1123
28. Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, R. J. Protein measurement with the Folin phenol reagent J. Biol. Chem. 1951, 193, 265-275
29. Szakács, T.; Veres, Z.; Vereczkey, L. Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes Pol. J. Pharmacol. 2001, 53, 11-19
30. Danhof, M.; de Boer, A. G.; de Groot-van der Vis, E.; Breimer, D. D. Assay of antipyrine and its primary metabolites in plasma, saliva and urine by high-performance liquid chromatography and some preliminary results in man Pharmacology 1979, 19, 215-220