메뉴 건너뛰기




Volumn 40, Issue 6, 1997, Pages 980-989

Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; MELOXICAM; NONSTEROID ANTIINFLAMMATORY AGENT; PIROXICAM; THIAZINE DERIVATIVE;

EID: 14444275534     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9607010     Document Type: Article
Times cited : (91)

References (49)
  • 1
    • 0015237292 scopus 로고
    • Inhibition of Prostaglandin Synthesis as a Mechanism of Action for Aspirin-Like Drugs
    • Vane, J. R. Inhibition of Prostaglandin Synthesis as a Mechanism of Action for Aspirin-Like Drugs. Nature 1971, 231, 232-237.
    • (1971) Nature , vol.231 , pp. 232-237
    • Vane, J.R.1
  • 2
    • 0026322957 scopus 로고
    • A Serum- and Glucocorticoid-Regulated 4-Kilobase mRNA Encodes a Cyclooxygenase Related Protein
    • (a) O'Banion, M. K.; Sadowski, H. B.; Winn, V.; Young, D. A. A Serum- and Glucocorticoid-Regulated 4-Kilobase mRNA Encodes a Cyclooxygenase Related Protein. J. Biol. Chem. 1991, 266, 23261-23267.
    • (1991) J. Biol. Chem. , vol.266 , pp. 23261-23267
    • O'Banion, M.K.1    Sadowski, H.B.2    Winn, V.3    Young, D.A.4
  • 3
    • 0026735231 scopus 로고
    • cDNA Cloning and Functional Activity of a Glucocorticoid-Regulated Inflammatory Cyclooxygenase
    • (b) O'Banion, M. K.; Winn, V.; Young, D. A. cDNA Cloning and Functional Activity of a Glucocorticoid-Regulated Inflammatory Cyclooxygenase. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 4888-4892.
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 4888-4892
    • O'Banion, M.K.1    Winn, V.2    Young, D.A.3
  • 4
    • 0026662385 scopus 로고
    • Dexamethasone Inhibits Mitogen Induction of the TIS10 Prostaglandin Synthase/Cyclooxygenase Gene
    • (c) Kujubu, D. A.; Herschmann, H. R. Dexamethasone Inhibits Mitogen Induction of the TIS10 Prostaglandin Synthase/Cyclooxygenase Gene. J. Biol. Chem. 1992, 267, 7991-7994.
    • (1992) J. Biol. Chem. , vol.267 , pp. 7991-7994
    • Kujubu, D.A.1    Herschmann, H.R.2
  • 5
    • 0028044609 scopus 로고
    • Towards a Better Aspirin
    • (a) Vane, J. R. Towards a Better Aspirin. Nature 1994, 367, 215-216.
    • (1994) Nature , vol.367 , pp. 215-216
    • Vane, J.R.1
  • 6
    • 0028926813 scopus 로고
    • New Insights into the Mode of Action of Anti-Inflammatory Drugs
    • (b) Vane, J. R.; Botting, R. M. New Insights into the Mode of Action of Anti-Inflammatory Drugs. Inflamm Res. 1995, 44, 1-10.
    • (1995) Inflamm Res. , vol.44 , pp. 1-10
    • Vane, J.R.1    Botting, R.M.2
  • 7
    • 0027912932 scopus 로고
    • PGH Synthase Isoenzyme Selectivity: The Potential for Safer Non-steroidal Antiinflammatory Drugs
    • (c) DeWitt, D. L.; Meade, E. A.; Smith, W. L. PGH Synthase Isoenzyme Selectivity: The Potential for Safer Non-steroidal Antiinflammatory Drugs. Am. J. Med. 1993, 95 (Suppl. 2A), 2A-40S-2A-44S.
    • (1993) Am. J. Med. , vol.95 , Issue.SUPPL. 2A
    • DeWitt, D.L.1    Meade, E.A.2    Smith, W.L.3
  • 8
    • 0027480087 scopus 로고
    • Differential Inhibition of Prostaglandin Endoperoxide Synthase (Cyclooxygenase) Isoenzymes by Aspirin and Other Non-Steroidal Antiinflammatory Drugs
    • (a) Meade, E. A.; Smith, W. L.; DeWitt, D. L. Differential Inhibition of Prostaglandin Endoperoxide Synthase (Cyclooxygenase) Isoenzymes by Aspirin and Other Non-Steroidal Antiinflammatory Drugs. J. Biol. Chem. 1993, 268, 6610-6614.
    • (1993) J. Biol. Chem. , vol.268 , pp. 6610-6614
    • Meade, E.A.1    Smith, W.L.2    DeWitt, D.L.3
  • 9
    • 0027986841 scopus 로고
    • Differential Inhibition of Human Prostaglandin Endoperoxide H Synthases-1 and -2 by Nonsteroidal Anti-Inflammatory Drugs
    • (b) Laneuville, O.; Breuer, D. K.; DeWitt, D. L.; Hla, T.; Funk, C. D.; Smith, W. L. Differential Inhibition of Human Prostaglandin Endoperoxide H Synthases-1 and -2 by Nonsteroidal Anti-Inflammatory Drugs. J. Pharmacol. Exp. Ther. 1994, 277, 927-934.
    • (1994) J. Pharmacol. Exp. Ther. , vol.277 , pp. 927-934
    • Laneuville, O.1    Breuer, D.K.2    DeWitt, D.L.3    Hla, T.4    Funk, C.D.5    Smith, W.L.6
  • 10
    • 0027146692 scopus 로고
    • Selectivity of Nonsteroidal Antiinflammatory Drugs as Inhibitors of Constitutive and Inducible Cyclooxygenase
    • (c) Mitchell, J. A.; Akerasereenont, P.; Thiemermann, C.; Flower, R. J. Selectivity of Nonsteroidal Antiinflammatory Drugs as Inhibitors of Constitutive and Inducible Cyclooxygenase. Proc. Natl. Acad. Sci. U.S.A. 1994, 90, 11693-11697.
    • (1994) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 11693-11697
    • Mitchell, J.A.1    Akerasereenont, P.2    Thiemermann, C.3    Flower, R.J.4
  • 11
    • 0029029296 scopus 로고
    • Inhibition of Constitutive and Inducible Cyclooxygenase Activity in Human Platelets and Mononuclear Cells by NSAIDS and Cox-2 Inhibitors
    • (d) Grossman, C. J.; Wiseman, J.; Lucas, F. S.; Treuethick, M. A.; Birch, P. J. Inhibition of Constitutive and Inducible Cyclooxygenase Activity in Human Platelets and Mononuclear Cells by NSAIDS and Cox-2 Inhibitors. Inflamm Res. 1995, 44, 253-257.
    • (1995) Inflamm Res. , vol.44 , pp. 253-257
    • Grossman, C.J.1    Wiseman, J.2    Lucas, F.S.3    Treuethick, M.A.4    Birch, P.J.5
  • 12
    • 0028089109 scopus 로고
    • NS-398, a New Anti-inflammatory Agent, Selectively Inhibits Prostaglandin G/H Synthase/Cyclooxygenase (COX-2) Activity In Vitro
    • Futaki, N.; Takahashi, S.; Yokoyama, I.; Arai, I.; Higuchi, S.; Otomo, S. NS-398, a New Anti-inflammatory Agent, Selectively Inhibits Prostaglandin G/H Synthase/Cyclooxygenase (COX-2) Activity In Vitro. Prostaglandins 1994, 47, 55-59.
    • (1994) Prostaglandins , vol.47 , pp. 55-59
    • Futaki, N.1    Takahashi, S.2    Yokoyama, I.3    Arai, I.4    Higuchi, S.5    Otomo, S.6
  • 14
    • 0017191297 scopus 로고
    • 4-Nitro-2-Phenoxymethanesulfonamide (R-805): A Chemically Novel Anti-inflammatory Agent
    • (a) Swingle, K. F.; Moore, G. G. I.; Grant, T, J. 4-Nitro-2-Phenoxymethanesulfonamide (R-805): a Chemically Novel Anti-inflammatory Agent. Arch. Int. Pharmacodyn. 1976, 221, 132-139.
    • (1976) Arch. Int. Pharmacodyn. , vol.221 , pp. 132-139
    • Swingle, K.F.1    Moore, G.G.I.2    Grant, T.J.3
  • 19
    • 0028860983 scopus 로고
    • Anti-Inflammatory, Analgesic, Antipyretic and Related Properties of Meloxicam, a New Nonsteroidal Anti-Inflammatory Agent with Favourable Gastrointestinal Tolerance
    • (b) Engelhardt, G.; Homma, D.; Schlegel, K.; Ultzmann, R.; Schnitzler, C. Anti-Inflammatory, Analgesic, Antipyretic and Related Properties of Meloxicam, a New Nonsteroidal Anti-Inflammatory Agent with Favourable Gastrointestinal Tolerance. Inflamm. Res. 1995, 44, 423-433.
    • (1995) Inflamm. Res. , vol.44 , pp. 423-433
    • Engelhardt, G.1    Homma, D.2    Schlegel, K.3    Ultzmann, R.4    Schnitzler, C.5
  • 20
    • 0029619752 scopus 로고
    • Meloxicam: A Potent Inhibitor of Adjuvant Arthritis in the Lewis Rat
    • (c) Engelhardt, G.; Homma, D.; Schnitzler, C. Meloxicam: A Potent Inhibitor of Adjuvant Arthritis in the Lewis Rat. Inflamm. Res. 1995, 44, 548-545.
    • (1995) Inflamm. Res. , vol.44 , pp. 548-1545
    • Engelhardt, G.1    Homma, D.2    Schnitzler, C.3
  • 21
    • 0029866403 scopus 로고    scopus 로고
    • A 4-Week Double -Blind, Parallel- Group Study to Compare the Gastrointestinal Effects of Meloxicam 7.5 mg, Meloxicam 15 mg, Piroxicam 20 mg and Placebo by Means of Faecal Blood Loss, Endoscopy and Symptoms Evaluation in Healthy Volunteers
    • (a) Patoia, L; Santucci, L.; Furno, P. et al. A 4-Week Double -Blind, Parallel- Group Study to Compare the Gastrointestinal Effects of Meloxicam 7.5 mg, Meloxicam 15 mg, Piroxicam 20 mg and Placebo by Means of Faecal Blood Loss, Endoscopy and Symptoms Evaluation in Healthy Volunteers. Br. J. Rheumatol. 1996, 35 (Suppl. 1), 61-67.
    • (1996) Br. J. Rheumatol. , vol.35 , Issue.1 SUPPL. , pp. 61-67
    • Patoia, L.1    Santucci, L.2    Furno, P.3
  • 22
    • 0029932265 scopus 로고    scopus 로고
    • An Open Study to Assess the Safety and Tolerability of Meloxicam 15 mg in Subjects with Rheumatoid Disease and Mild Renal Impairment
    • (b) Bird, H. A.; Bevis, P. J. R.; Lapham, G. An Open Study to Assess the Safety and Tolerability of Meloxicam 15 mg in Subjects with Rheumatoid Disease and Mild Renal Impairment. Br. J. Rheumatol. 1996, 35 (Suppl. 1), 56-60.
    • (1996) Br. J. Rheumatol. , vol.35 , Issue.1 SUPPL. , pp. 56-60
    • Bird, H.A.1    Bevis, P.J.R.2    Lapham, G.3
  • 23
    • 0029979358 scopus 로고    scopus 로고
    • Safety of Meloxicam: A Global Analysis of Clinical Trials
    • (c) Distel, M.; Mueller, C.; Bluhmki, E.; Fries, J. Safety of Meloxicam: A Global Analysis of Clinical Trials. Br. J. Rheumatol. 1996, 35 (Suppl. 1), 68-77.
    • (1996) Br. J. Rheumatol. , vol.35 , Issue.1 SUPPL. , pp. 68-77
    • Distel, M.1    Mueller, C.2    Bluhmki, E.3    Fries, J.4
  • 25
    • 0030030129 scopus 로고    scopus 로고
    • Meloxicam: Influence on Arachidonic Acid Metabolism. Part I. In Vitro Findings
    • (b) Engelhardt, G.; Bögel, R.; Schnitzer, C.; Utzmatin, R. Meloxicam: Influence on Arachidonic Acid Metabolism. Part I. In Vitro Findings. Biochem. Pharmacol. 1996, 51, 21-28.
    • (1996) Biochem. Pharmacol. , vol.51 , pp. 21-28
    • Engelhardt, G.1    Bögel, R.2    Schnitzer, C.3    Utzmatin, R.4
  • 26
    • 0030061289 scopus 로고    scopus 로고
    • Meloxicam: Influence on Arachidonic Acid Metabolism. Part II. In Vivo Findings
    • (c) Engelhardt, G.; Bögel, R.; Schnitzer, C.; Utzmann, R. Meloxicam: Influence on Arachidonic Acid Metabolism. Part II. In Vivo Findings. Biochem. Pharmacol. 1996, 51, 29-38.
    • (1996) Biochem. Pharmacol. , vol.51 , pp. 29-38
    • Engelhardt, G.1    Bögel, R.2    Schnitzer, C.3    Utzmann, R.4
  • 27
    • 0015184521 scopus 로고
    • Synthesis and Antiinflammatory Activity of Some 3-Carboxamides of 2-Alkyl-4-hydroxy-2H-1,2-benzothiazine 1,1-Dioxides
    • Lombardino, J. G.; Wiseman, E. H.; McLamore, W. M. Synthesis and Antiinflammatory Activity of Some 3-Carboxamides of 2-Alkyl-4-hydroxy-2H-1,2-benzothiazine 1,1-Dioxides. J. Med. Chem. 1971, 14, 1171-1175.
    • (1971) J. Med. Chem. , vol.14 , pp. 1171-1175
    • Lombardino, J.G.1    Wiseman, E.H.2    McLamore, W.M.3
  • 28
    • 33947290164 scopus 로고
    • Preparation of Substituted 1,2-Benzoisothiazolin-3-one 1,1-Dioxides (o-Benzoic Sulfimides)
    • Lombardino, J. G. Preparation of Substituted 1,2-Benzoisothiazolin-3-one 1,1-Dioxides (o-Benzoic Sulfimides). J. Org. Chem. 1971, 36, 1843-1845.
    • (1971) J. Org. Chem. , vol.36 , pp. 1843-1845
    • Lombardino, J.G.1
  • 29
    • 0015621734 scopus 로고
    • Potent Antiinflammatory N-Heterocyclic 3-Carboxamides of 4-Hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-Dioxide
    • (b) Lombardino, J. G.; Wiseman, E. H.; Chiaini, J. Potent Antiinflammatory N-Heterocyclic 3-Carboxamides of 4-Hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-Dioxide. J. Med. Chem. 1973, 16, 493-496.
    • (1973) J. Med. Chem. , vol.16 , pp. 493-496
    • Lombardino, J.G.1    Wiseman, E.H.2    Chiaini, J.3
  • 30
    • 0019944528 scopus 로고
    • Piroxicam and Other Anti-Inflammatory Oxicams
    • Lombardino, J. G.; Wiseman, E. H. Piroxicam and Other Anti-Inflammatory Oxicams. Med. Res. Rev. 1982, 2, 127-152.
    • (1982) Med. Res. Rev. , vol.2 , pp. 127-152
    • Lombardino, J.G.1    Wiseman, E.H.2
  • 31
    • 0015133043 scopus 로고
    • 3,4-Dihydro-2-alkyl-3-oxo-2H-1,2-benzothiazine-4-carboxamide 1,1-Dioxides
    • Lombardino, J. G.; Wiseman, E. H. 3,4-Dihydro-2-alkyl-3-oxo-2H-1,2-benzothiazine-4-carboxamide 1,1-Dioxides. J. Med. Chem. 1971, 14, 973-977.
    • (1971) J. Med. Chem. , vol.14 , pp. 973-977
    • Lombardino, J.G.1    Wiseman, E.H.2
  • 34
    • 84987284930 scopus 로고
    • Synthesis of 4-Hydroxy-2-methylisocarbostyril-3-carboxanilides
    • Lombardino, J. G. Synthesis of 4-Hydroxy-2-methylisocarbostyril-3-carboxanilides. J. Heterocycl. Chem. 1970, 7, 1057-1060.
    • (1970) J. Heterocycl. Chem. , vol.7 , pp. 1057-1060
    • Lombardino, J.G.1
  • 35
    • 14444287568 scopus 로고
    • On the Transmission of Polar Effects by the Amide Moiety
    • Kadin, S. B. On the Transmission of Polar Effects by the Amide Moiety. J. Org. Chem. 1971, 36, 1160-1161.
    • (1971) J. Org. Chem. , vol.36 , pp. 1160-1161
    • Kadin, S.B.1
  • 36
    • 0028023164 scopus 로고
    • Novel Spirosuccinimide Aldose Reductase Inhibitors Derived from Isoquinoline-1,3-diones: 2[(4-Bromo-2-fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4(1H), 3′-pyrrolidine]-1,2′,3,5′(2H)-tetrone and Congeners. 1
    • Malamas, M. S.; Hohman, T. C.; Millen, J. Novel Spirosuccinimide Aldose Reductase Inhibitors Derived from Isoquinoline-1,3-diones: 2[(4-Bromo-2-fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4(1H), 3′-pyrrolidine]-1,2′,3,5′(2H)-tetrone and Congeners. 1. J. Med. Chem. 1994, 37, 2043-2058.
    • (1994) J. Med. Chem. , vol.37 , pp. 2043-2058
    • Malamas, M.S.1    Hohman, T.C.2    Millen, J.3
  • 40
    • 66449095380 scopus 로고
    • Uber Thiochromanone und Umwendlungsprodukte
    • (a) Krollpfeiffer, F.; Schultze, H.; Uber Thiochromanone und Umwendlungsprodukte. (Thiochromanones and Transformation Products.) Ber. 1923, 56B, 1819-1824.
    • (1923) Ber. , vol.56 B , pp. 1819-1824
    • Krollpfeiffer, F.1    Schultze, H.2
  • 41
    • 0026589294 scopus 로고
    • Herstellung von Stereoisomeren 3-Sulfinylbuttersauren aus (R)- und (S)-4-methyl-2-oxetanon
    • (b) Breitschoh, R.; Seebach, D. Herstellung von Stereoisomeren 3-Sulfinylbuttersauren aus (R)- und (S)-4-methyl-2-oxetanon. (Preparation of Stereoisomers of 3-Sulfinylbutyric Acid From (R)- and (S)-4-Methyl-2-oxetanone.) Synthesis 1992, 83-89.
    • (1992) Synthesis , pp. 83-89
    • Breitschoh, R.1    Seebach, D.2
  • 42
    • 85082554095 scopus 로고
    • Synthesis of 22-Dimethyl-2H-thiochromens, the Sulfur Analogs of Precocenes
    • (c) Tercio, J.; Ferreira, B.; Catani, V.; Comasseto, J. V. Synthesis of 22-Dimethyl-2H-thiochromens, the Sulfur Analogs of Precocenes. Synthesis 1987, 149-153.
    • (1987) Synthesis , pp. 149-153
    • Tercio, J.1    Ferreira, B.2    Catani, V.3    Comasseto, J.V.4
  • 43
    • 0015540369 scopus 로고
    • 1,2-Benzothiazines. 6. 3-Carbamoyl-4-hydroxy-2-H-1,2-benzothiazine 1,1-Dioxides as Antiinflammatory Agents
    • Zinnes, H.; Lindo, N. A.; Sicar, J. C.; Schwartz, M. L.; Shavel, J., Jr. 1,2-Benzothiazines. 6. 3-Carbamoyl-4-hydroxy-2-H-1,2-benzothiazine 1,1-Dioxides as Antiinflammatory Agents. J. Med. Chem. 1973, 16, 44-48.
    • (1973) J. Med. Chem. , vol.16 , pp. 44-48
    • Zinnes, H.1    Lindo, N.A.2    Sicar, J.C.3    Schwartz, M.L.4    Shavel Jr., J.5
  • 45
    • 0028339780 scopus 로고
    • Acetylation of Human Prostaglandin Endoperoxide Synthase-2 (cyclooxygenase-2) by Aspirin
    • Lecompte, M.; Laneuville, O.; Ji, C.; DeWitt, D. L.; Smith, W. L. Acetylation of Human Prostaglandin Endoperoxide Synthase-2 (cyclooxygenase-2) by Aspirin. J. Biol. Chem. 1994, 269, 13207-13215.
    • (1994) J. Biol. Chem. , vol.269 , pp. 13207-13215
    • Lecompte, M.1    Laneuville, O.2    Ji, C.3    DeWitt, D.L.4    Smith, W.L.5
  • 48
    • 0019592046 scopus 로고
    • Pharmacokinetic and pharmacodynamic modeling in vivo
    • Holford, N. H. G.; Sheiner, L. B.; Pharmacokinetic and pharmacodynamic modeling in vivo. Crit. Rev. Bioeng. 1981, 5, 273-322.
    • (1981) Crit. Rev. Bioeng. , vol.5 , pp. 273-322
    • Holford, N.H.G.1    Sheiner, L.B.2
  • 49
    • 0020315441 scopus 로고
    • Kinetics of phamacologic response
    • Holford, N. H. G.; Sheiner, L. B. Kinetics of phamacologic response. Pharmacol Ther. 1982, 16, 143-166.
    • (1982) Pharmacol Ther. , vol.16 , pp. 143-166
    • Holford, N.H.G.1    Sheiner, L.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.