메뉴 건너뛰기




Volumn 112, Issue 43, 2008, Pages 10921-10930

Theoretical study of the phototoxicity of naproxen and the active form of nabumetone

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; HYDROCARBONS; NUCLEAR PROPULSION; OXYGEN; PH; PH EFFECTS; PHOTODEGRADATION;

EID: 55949134887     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp805614y     Document Type: Article
Times cited : (25)

References (35)
  • 1
    • 0037459940 scopus 로고    scopus 로고
    • Photodegradation of Nabumetone in aqueous solutions
    • Valero, M.; Costa, S. M. B. Photodegradation of Nabumetone in aqueous solutions. J. Photochem. Photobiol. A-Chem. 2003, 157, 93-101.
    • (2003) J. Photochem. Photobiol. A-Chem , vol.157 , pp. 93-101
    • Valero, M.1    Costa, S.M.B.2
  • 2
    • 27744603717 scopus 로고    scopus 로고
    • Simple and rapid determination of the active metabolite of nabumetone in biological fluids by heavy atom-induced room temperature phosphorescence
    • Pulgarin, J. A. M.; Molina, A. A.; Robles, I. S. F. Simple and rapid determination of the active metabolite of nabumetone in biological fluids by heavy atom-induced room temperature phosphorescence. Anal. Chim. Acta 2005, 554, 37-42.
    • (2005) Anal. Chim. Acta , vol.554 , pp. 37-42
    • Pulgarin, J.A.M.1    Molina, A.A.2    Robles, I.S.F.3
  • 3
    • 6344289552 scopus 로고    scopus 로고
    • Nabumetone-Therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis
    • Hedner, T.; Samulesson, O.; Wahrborg, P.; Wadenvik, H.; Ung, K. A.; Ekbom, A. Nabumetone-Therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis. Drugs 2004, 64, 2315-2343.
    • (2004) Drugs , vol.64 , pp. 2315-2343
    • Hedner, T.1    Samulesson, O.2    Wahrborg, P.3    Wadenvik, H.4    Ung, K.A.5    Ekbom, A.6
  • 4
    • 0002072018 scopus 로고    scopus 로고
    • Cyclodextrins as phototoxicity inhibitors in drug formulations: Studies on model systems involving naproxen and beta-cyclodextrin
    • Partyka, M.; Au, B. H.; Evans, C. H. Cyclodextrins as phototoxicity inhibitors in drug formulations: studies on model systems involving naproxen and beta-cyclodextrin. J. Photochem. Photobiol. A-Chem. 2001, 140, 67-74.
    • (2001) J. Photochem. Photobiol. A-Chem , vol.140 , pp. 67-74
    • Partyka, M.1    Au, B.H.2    Evans, C.H.3
  • 5
    • 0031116198 scopus 로고    scopus 로고
    • Photochemistry of naproxen in the presence of β-cyclodextrin
    • Jimenez, M. C.; Miranda, M. A.; Tormos, R. Photochemistry of naproxen in the presence of β-cyclodextrin. J. Photochem. Photobiol. 1997, 104, 119-121.
    • (1997) J. Photochem. Photobiol , vol.104 , pp. 119-121
    • Jimenez, M.C.1    Miranda, M.A.2    Tormos, R.3
  • 6
    • 27744548881 scopus 로고    scopus 로고
    • Risk of hospitalization with peptic ulcer disease or gastrointestinal hemorrhage associated with nabumetone, Arthrotec((R)), diclofenac, and naproxen in a population based cohort study
    • Ashworth, N. L.; Peloso, P. M.; Muhajarine, N.; Stang, M. Risk of hospitalization with peptic ulcer disease or gastrointestinal hemorrhage associated with nabumetone, Arthrotec((R)), diclofenac, and naproxen in a population based cohort study. J. Rheum. 2005, 32, 2212-2217.
    • (2005) J. Rheum , vol.32 , pp. 2212-2217
    • Ashworth, N.L.1    Peloso, P.M.2    Muhajarine, N.3    Stang, M.4
  • 7
    • 0037332251 scopus 로고    scopus 로고
    • Non-steroidal anti-inflammatory drug nabumetone, prevents indometacin-induced gastric damage via inhibition of neutrophil functions
    • Ishiwata, Y.; Okamoto, M.; Yokochi, S.; Hashimoto, H.; Nakamura, T.; Miyachi, A.; Naito, Y.; Yoshikawa, T. Non-steroidal anti-inflammatory drug nabumetone, prevents indometacin-induced gastric damage via inhibition of neutrophil functions. J. Pharm. Pharmacol. 2003, 55, 229-237.
    • (2003) J. Pharm. Pharmacol , vol.55 , pp. 229-237
    • Ishiwata, Y.1    Okamoto, M.2    Yokochi, S.3    Hashimoto, H.4    Nakamura, T.5    Miyachi, A.6    Naito, Y.7    Yoshikawa, T.8
  • 9
    • 0042626025 scopus 로고    scopus 로고
    • Comparative biotransformation and disposition studies of nabumetone in humans and minipigs using high-performance liquid chromatography with ultraviolet, fluorescence and mass spectrometric detection
    • Nobilis, M.; Kopecky, J.; Kvetina, J.; Svoboda, Z.; Pour, M.; Kunes, J.; Holcapek, M.; Kolarova, L. Comparative biotransformation and disposition studies of nabumetone in humans and minipigs using high-performance liquid chromatography with ultraviolet, fluorescence and mass spectrometric detection. J. Pharm. Biomed. Anal. 2003, 32, 641-656.
    • (2003) J. Pharm. Biomed. Anal , vol.32 , pp. 641-656
    • Nobilis, M.1    Kopecky, J.2    Kvetina, J.3    Svoboda, Z.4    Pour, M.5    Kunes, J.6    Holcapek, M.7    Kolarova, L.8
  • 13
    • 0032892585 scopus 로고    scopus 로고
    • Pseudoporphyria associated with Relafen therapy
    • Magro, C. M.; Crowson, A. N. Pseudoporphyria associated with Relafen therapy. J. Cutan. Pathol. 1999, 26, 42-47.
    • (1999) J. Cutan. Pathol , vol.26 , pp. 42-47
    • Magro, C.M.1    Crowson, A.N.2
  • 14
    • 0034143181 scopus 로고    scopus 로고
    • Bosca, F.; Canudas, N.; Marin, M. L.; Miranda, M. A. A photophysical and photochemical study of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic nonsteroidal antiinflammatory drug nabumetone. J. Photochem. Photobiol. 2000, 71, 173-177.
    • Bosca, F.; Canudas, N.; Marin, M. L.; Miranda, M. A. A photophysical and photochemical study of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic nonsteroidal antiinflammatory drug nabumetone. J. Photochem. Photobiol. 2000, 71, 173-177.
  • 15
    • 4344667389 scopus 로고    scopus 로고
    • Alkyl esters of 6-methoxy-2-naphthylacetic acid as potential prodrugs -synthesis, physicochemical properties, chemical stability and enzymatic hydrolysis
    • Wadhwa, L. K.; Chandiran, S.; Sharma, P. D. Alkyl esters of 6-methoxy-2-naphthylacetic acid as potential prodrugs -synthesis, physicochemical properties, chemical stability and enzymatic hydrolysis. Indian J. Chem. 2004, 43B, 1292-1298.
    • (2004) Indian J. Chem , vol.43 B , pp. 1292-1298
    • Wadhwa, L.K.1    Chandiran, S.2    Sharma, P.D.3
  • 17
    • 55949104120 scopus 로고    scopus 로고
    • www.drugbank.ca/drugs/DB00788.
  • 18
    • 23844550561 scopus 로고    scopus 로고
    • Photosensitizing properties of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic non-steroidal anti-inflammatory and analgesic drug nabumetone
    • Canudas, N.; Zamora, D.; Villamizar, J. E.; Fuentes, J.; Castelli, C.: Taddei, A. Photosensitizing properties of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic non-steroidal anti-inflammatory and analgesic drug nabumetone. Pharmazie 2005, 60, 604-608.
    • (2005) Pharmazie , vol.60 , pp. 604-608
    • Canudas, N.1    Zamora, D.2    Villamizar, J.E.3    Fuentes, J.4    Castelli, C.5    Taddei, A.6
  • 19
    • 0032214758 scopus 로고    scopus 로고
    • Characterization of the transient intermediates generated from the photoexcitation of nabumetone: A comparison with naproxen
    • Martinez, L. J.; Scaiano, J. C. Characterization of the transient intermediates generated from the photoexcitation of nabumetone: A comparison with naproxen. J. Photochem. Photobiol. 1998, 68, 646-651.
    • (1998) J. Photochem. Photobiol , vol.68 , pp. 646-651
    • Martinez, L.J.1    Scaiano, J.C.2
  • 20
    • 0030980235 scopus 로고    scopus 로고
    • Time-resolved near infrared studies on singlet oxygen production by the photosensitizing 2-arylpropionic acids
    • De La Pena, D.; Marti, C.; Nonell, S.; Martinez, L. A.; Miranda, M. A. Time-resolved near infrared studies on singlet oxygen production by the photosensitizing 2-arylpropionic acids. J. Photochem. Photobiol. 1997, 65, 828-832.
    • (1997) J. Photochem. Photobiol , vol.65 , pp. 828-832
    • De La Pena, D.1    Marti, C.2    Nonell, S.3    Martinez, L.A.4    Miranda, M.A.5
  • 21
    • 34247202657 scopus 로고    scopus 로고
    • Mechanism of Photoinduced Decomposition of Ketoprofen
    • Musa, K. A. K.; Matxain, J. M.; Eriksson, L. A. Mechanism of Photoinduced Decomposition of Ketoprofen. J. Med. Chem. 2007, 50, 1735-1743.
    • (2007) J. Med. Chem , vol.50 , pp. 1735-1743
    • Musa, K.A.K.1    Matxain, J.M.2    Eriksson, L.A.3
  • 22
    • 37149001436 scopus 로고    scopus 로고
    • Theoretical study of ibuprofen phototoxicity
    • Musa, K. A. K.; Eriksson, L. A. Theoretical study of ibuprofen phototoxicity. J. Phys. Chem. B. 2007, 111, 13345-13352.
    • (2007) J. Phys. Chem. B , vol.111 , pp. 13345-13352
    • Musa, K.A.K.1    Eriksson, L.A.2
  • 23
    • 55949111706 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, lyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann. R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keit
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; lyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann. R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, rev. B.02; Gaussian, Inc.: Wallingford, CT, 2004.
  • 24
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. 3. The role of exact exchange
    • Becke, A. D. Density-functional thermochemistry. 3. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648-5652.
    • (1993) J. Chem. Phys , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 25
    • 33751157732 scopus 로고    scopus 로고
    • Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J. Phys. Chem. 1994, 98, 11623-11627.
    • Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J. Phys. Chem. 1994, 98, 11623-11627.
  • 26
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. 1988, 37, 785.
    • (1988) Phys. Rev , vol.37 , pp. 785
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 27
    • 84961979198 scopus 로고    scopus 로고
    • Continuum solvation models: A new approach to the problem of solute's charge distribution and cavity boundaries
    • Mennucci, B.; Tomasi, J. Continuum solvation models: A new approach to the problem of solute's charge distribution and cavity boundaries. Chem. Phys. 1997, 106, 5151-5158.
    • (1997) Chem. Phys , vol.106 , pp. 5151-5158
    • Mennucci, B.1    Tomasi, J.2
  • 28
    • 84961986752 scopus 로고    scopus 로고
    • New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution
    • Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution. J. Chem. Phys. 2002, 117, 43-54.
    • (2002) J. Chem. Phys , vol.117 , pp. 43-54
    • Cossi, M.1    Scalmani, G.2    Rega, N.3    Barone, V.4
  • 29
    • 0031209054 scopus 로고    scopus 로고
    • A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics
    • Cances, E.; Mennucci, B.; Tomasi, J. A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics. J. Chem. Phys. 1997, 107, 3032-3041.
    • (1997) J. Chem. Phys , vol.107 , pp. 3032-3041
    • Cances, E.1    Mennucci, B.2    Tomasi, J.3
  • 30
    • 0030570285 scopus 로고    scopus 로고
    • Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory
    • Bauernschmitt, R.; Ahlrichs, R. Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem. Phys. Lett. 1996, 256, 454-464.
    • (1996) Chem. Phys. Lett , vol.256 , pp. 454-464
    • Bauernschmitt, R.1    Ahlrichs, R.2
  • 31
    • 0000287603 scopus 로고    scopus 로고
    • Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold
    • Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold. J. Chem. Phys. 1998, 108, 4439-4449.
    • (1998) J. Chem. Phys , vol.108 , pp. 4439-4449
    • Casida, M.E.1    Jamorski, C.2    Casida, K.C.3    Salahub, D.R.4
  • 32
    • 0032533083 scopus 로고    scopus 로고
    • An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules
    • Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules. J. Chem. Phys. 1998, 109, 8218-8224.
    • (1998) J. Chem. Phys , vol.109 , pp. 8218-8224
    • Stratmann, R.E.1    Scuseria, G.E.2    Frisch, M.J.3
  • 35
    • 0023953665 scopus 로고
    • A comparative study of the photochemistry of the non-steroidal anti-inflammatory drugs, naproxen, benoxaprofen and indomethacin
    • Moore, D. E.; Chappuis, P. P. A comparative study of the photochemistry of the non-steroidal anti-inflammatory drugs, naproxen, benoxaprofen and indomethacin. J. Photochem. Photobiol. 1988, 47, 173-180.
    • (1988) J. Photochem. Photobiol , vol.47 , pp. 173-180
    • Moore, D.E.1    Chappuis, P.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.