메뉴 건너뛰기




Volumn 73, Issue 8, 2009, Pages

A receptor-grounded approach to teaching nonsteroidal antiinflammatory drug chemistry and structure-activity relationships

Author keywords

Medicinal chemistry; Nonsteroidal antiinflammatory drugs

Indexed keywords

CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN SYNTHASE INHIBITOR;

EID: 74749094736     PISSN: 00029459     EISSN: 15536467     Source Type: Journal    
DOI: 10.5688/aj7308143     Document Type: Article
Times cited : (15)

References (22)
  • 2
    • 31044452640 scopus 로고    scopus 로고
    • The productive conformation of prostaglandin G2 at peroxidase site of prostaglandin endoperoide H synthase: Docking, molecular dynamics, and site-directed mutagenesis studies
    • Chubb AJ, Fitzgerald DJ, Nolan KB, Moman E. The productive conformation of prostaglandin G2 at peroxidase site of prostaglandin endoperoide H synthase: docking, molecular dynamics, and site-directed mutagenesis studies. Biochemistry. 2006;45(3):811-820.
    • (2006) Biochemistry , vol.45 , Issue.3 , pp. 811-820
    • Chubb, A.J.1    Fitzgerald, D.J.2    Nolan, K.B.3    Moman, E.4
  • 3
    • 33750840296 scopus 로고    scopus 로고
    • The chemically elegant proton pump inhibitors: A self-contained, clinically relevant medicinal chemistry lesson
    • Article
    • Roche VF. The chemically elegant proton pump inhibitors: A self-contained, clinically relevant medicinal chemistry lesson. Am J Pharm Educ. 2006;70(5):Article 101.
    • (2006) Am J Pharm Educ , vol.70 , Issue.5 , pp. 101
    • Roche, V.F.1
  • 4
    • 27744593677 scopus 로고    scopus 로고
    • Antihyperlipidemic statins: A self-contained, clinically relevant medicinal chemistry lesson
    • Article
    • Roche VF. Antihyperlipidemic statins: a self-contained, clinically relevant medicinal chemistry lesson. Am J Pharm Educ. 2005; 69(4):Article 77.
    • (2005) Am J Pharm Educ , vol.69 , Issue.4 , pp. 77
    • Roche, V.F.1
  • 5
    • 0035971116 scopus 로고    scopus 로고
    • Prostaglandin endoperoxide H synthase-1
    • Thuresson ED, Lakkides KM, Rieke CJ, et al. Prostaglandin endoperoxide H synthase-1. J Biol Chem. 2001;276(13):10347-10359.
    • (2001) J Biol Chem , vol.276 , Issue.13 , pp. 10347-10359
    • Thuresson, E.D.1    Lakkides, K.M.2    Rieke, C.J.3
  • 6
    • 33644863929 scopus 로고    scopus 로고
    • Molecular dynamics simulations of arachidonic acid complexes with COX-1 and COX-2: Insights into equilibrium behavior
    • Furse KE, Pratt DA, Porter NA, Lybrand TP. Molecular dynamics simulations of arachidonic acid complexes with COX-1 and COX-2: insights into equilibrium behavior. Biochemistry. 2006;45(10): 3198-3205.
    • (2006) Biochemistry , vol.45 , Issue.10 , pp. 3198-3205
    • Furse, K.E.1    Pratt, D.A.2    Porter, N.A.3    Lybrand, T.P.4
  • 7
    • 0342803187 scopus 로고    scopus 로고
    • Modeling cyclooxygenase inhibition: Implication of active site hydration on the selectivity of ketoprofen analogues
    • Palomer A, Perez JJ, Navea S, Llorens O, Pascual J, Garcia L, Mauleon D. Modeling cyclooxygenase inhibition: implication of active site hydration on the selectivity of ketoprofen analogues. J Med Chem. 2000;43(11):2280-2284.
    • (2000) J Med Chem , vol.43 , Issue.11 , pp. 2280-2284
    • Palomer, A.1    Perez, J.J.2    Navea, S.3    Llorens, O.4    Pascual, J.5    Garcia, L.6    Mauleon, D.7
  • 8
    • 16744369033 scopus 로고    scopus 로고
    • Structural insights into the stereochemistry of the cyclooxygenase reaction
    • Kiefer JR, Pawlitz JL, Moreland KT, et al. Structural insights into the stereochemistry of the cyclooxygenase reaction. Nature. 2000;405:97-101.
    • (2000) Nature , vol.405 , pp. 97-101
    • Kiefer, J.R.1    Pawlitz, J.L.2    Moreland, K.T.3
  • 9
    • 0034010844 scopus 로고    scopus 로고
    • Spatial requirements for 15-(R)-hydroxy-5Z-8Z-11Z-13E-eicosatetraenoic acid synthesis within the cyclooxygenase active site of murine COX-2. Why acetylated COX-1 does not synthesize 15-(R)-HETE
    • Rowlinson SW, Crews BC, Goodwin DC, Schneider C, Gierse JK, Marnett LJ. Spatial requirements for 15-(R)-hydroxy-5Z-8Z-11Z-13E-eicosatetraenoic acid synthesis within the cyclooxygenase active site of murine COX-2. Why acetylated COX-1 does not synthesize 15-(R)-HETE. J Biol Chem. 2000;275(9):6586- 6591.
    • (2000) J Biol Chem , vol.275 , Issue.9 , pp. 6586-6591
    • Rowlinson, S.W.1    Crews, B.C.2    Goodwin, D.C.3    Schneider, C.4    Gierse, J.K.5    Marnett, L.J.6
  • 10
    • 0030461132 scopus 로고    scopus 로고
    • Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents
    • Kurumbail RG, Stevens AM, Gierse JK, et al. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature. 1996;384(6610):644-648.
    • (1996) Nature , vol.384 , Issue.6610 , pp. 644-648
    • Kurumbail, R.G.1    Stevens, A.M.2    Gierse, J.K.3
  • 11
    • 33745161107 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of linear phenylethynylbenzenesulfonamide regioisomers as cyclooxygenase-1/-2 (COX-1/-2) inhibitors
    • Anana R, Rap PNP, Chen Q-H, Knaus EE. Synthesis and biological evaluation of linear phenylethynylbenzenesulfonamide regioisomers as cyclooxygenase-1/-2 (COX-1/-2) inhibitors. Bioorganic Med Chem. 2006;14:5259-5265.
    • (2006) Bioorganic Med Chem , vol.14 , pp. 5259-5265
    • Anana, R.1    Rap, P.N.P.2    Chen, Q.-H.3    Knaus, E.E.4
  • 12
    • 0035145462 scopus 로고    scopus 로고
    • Etoricoxib (MK-0662):Preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2
    • Riendeau D, Percival MD, Brideau C, et al. Etoricoxib (MK-0662):Preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2. J Pharmacol Exper Ther. 2001;296(2):558-566.
    • (2001) J Pharmacol Exper Ther , vol.296 , Issue.2 , pp. 558-566
    • Riendeau, D.1    Percival, M.D.2    Brideau, C.3
  • 13
    • 0002742794 scopus 로고    scopus 로고
    • Nonsteroidal anti-inflammatory drugs
    • Williams DA, Lemke TL, eds, 6th ed. Baltimore, MD: Lippincott Williams & Wilkins;
    • Borne R, Levi M, Wilson N. Nonsteroidal anti-inflammatory drugs. In: Williams DA, Lemke TL, eds. Foye's Principles of Medicinal Chemistry, 6th ed. Baltimore, MD: Lippincott Williams & Wilkins; 2008:970.
    • (2008) Foye's Principles of Medicinal Chemistry , pp. 970
    • Borne, R.1    Levi, M.2    Wilson, N.3
  • 14
    • 34948902032 scopus 로고    scopus 로고
    • Structural basis of enantioselective inhibition of cyclooxygenase-1 by S-alpha-substituted indomethacin ethanolamides
    • Harman CA, Turman MV, Kozak KR, et al. Structural basis of enantioselective inhibition of cyclooxygenase-1 by S-alpha-substituted indomethacin ethanolamides. J Biol Chem. 2007; 282:28096-28105.
    • (2007) J Biol Chem , vol.282 , pp. 28096-28105
    • Harman, C.A.1    Turman, M.V.2    Kozak, K.R.3
  • 15
    • 0242580725 scopus 로고    scopus 로고
    • A novel mechanism of cyclooxygenase-2 inhibition involving interactions with Ser-530 and Tyr-385
    • Rowlinson SW, Kiefer JR, Prusakiewicz JJ, et al. A novel mechanism of cyclooxygenase-2 inhibition involving interactions with Ser-530 and Tyr-385. J Biol Chem. 2003;278:45763-45769.
    • (2003) J Biol Chem , vol.278 , pp. 45763-45769
    • Rowlinson, S.W.1    Kiefer, J.R.2    Prusakiewicz, J.J.3
  • 16
    • 84860134058 scopus 로고    scopus 로고
    • Accessed September 8, 2009
    • RCSB Protein Data Bank. http://www.rcsb.org/pdb/static.do?p=search/index. html. Accessed September 8, 2009.
    • RCSB Protein Data Bank
  • 18
    • 0032579940 scopus 로고    scopus 로고
    • Mechanism of action of nonsteroidal anti-inflammatory drugs
    • Vane JR, Gotting RM. Mechanism of action of nonsteroidal anti-inflammatory drugs. Am J Med. 1998;104(3A):2S-8S.
    • (1998) Am J Med , vol.104 , Issue.3 A
    • Vane, J.R.1    Gotting, R.M.2
  • 19
    • 10644285687 scopus 로고    scopus 로고
    • Molecular basis of the time-dependent inhibition of cyclooxygenase by indomethacin
    • Prusakiewicz JJ, Felts AS, Mackenzie BS, Marnett LJ. Molecular basis of the time-dependent inhibition of cyclooxygenase by indomethacin. Biochemistry. 2005;43: 15439-15445.
    • (2005) Biochemistry , vol.43 , pp. 15439-15445
    • Prusakiewicz, J.J.1    Felts, A.S.2    Mackenzie, B.S.3    Marnett, L.J.4
  • 20
    • 42449127113 scopus 로고    scopus 로고
    • Markers of electrophilic stress caused by chemically reactive metabolites in human hepatocytes
    • Takakusa H, Masumoto H, Mitsuru A, Okazaki O, Sudo K. Markers of electrophilic stress caused by chemically reactive metabolites in human hepatocytes. Drug Metab Dispos. 2008; 36(5):816-823.
    • (2008) Drug Metab Dispos , vol.36 , Issue.5 , pp. 816-823
    • Takakusa, H.1    Masumoto, H.2    Mitsuru, A.3    Okazaki, O.4    Sudo, K.5
  • 21
    • 60549099523 scopus 로고    scopus 로고
    • Improving pharmacy students' understanding and long-term retention of acid-base chemistry
    • Article
    • Roche VF. Improving pharmacy students' understanding and long-term retention of acid-base chemistry. Am J Pharm Educ. 2007;71(6):Article 122.
    • (2007) Am J Pharm Educ , vol.71 , Issue.6 , pp. 122
    • Roche, V.F.1
  • 22
    • 74749103626 scopus 로고    scopus 로고
    • Roche VF, Zito SW. Development and evaluation of a new computerized medicinal chemistry case study on NSAID chemistry and therapeutics: the Drugfather [abstract]. Meeting Abstracts. 109th Annual Meeting of the American Association of Colleges of Pharmacy, Chicago, Illinois, July 19-23, 2008. Am J Pharm Educ. 2008; 72(3):Article 72.
    • Roche VF, Zito SW. Development and evaluation of a new computerized medicinal chemistry case study on NSAID chemistry and therapeutics: the Drugfather [abstract]. Meeting Abstracts. 109th Annual Meeting of the American Association of Colleges of Pharmacy, Chicago, Illinois, July 19-23, 2008. Am J Pharm Educ. 2008; 72(3):Article 72.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.