Phototoxicity associated with diclofenac: A photophysical, photochemical, and photobiological study on the drug and its photoproducts

Chemical Research in Toxicology

Volumn 11, Issue 8, 1998, Pages 946-952

  Encinas, Susana ^a   Bosca, Francisco ^a   Miranda, Miguel A ^a  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DICLOFENAC;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; HALOGENATION; HEMOLYSIS; PHOTOLYSIS; PHOTOSENSITIZATION; PHOTOTOXICITY; TARGET CELL;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DERMATITIS, PHOTOTOXIC; DICLOFENAC; ERYTHROCYTES; LIGHT; LIPID PEROXIDATION;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0031817392     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9800708     Document Type: Article

References (32)

1. Ophaswongse, S., and Maibach, H. (1993) Topical nonsteroidal antiinflammatory drugs: allergic and photoallergic contact dermatitis and phototoxicity. Contact Dermatitis 29, 57-64.
2. Gould, J. W., Mercurio, M. G., and Elmets, C. A. (1995) Cutaneous photosensitivity diseases induced by exogenous agents. J. Am. Acad. Dermatol. 33, 551-573.
3. Kochevar, I. E. (1989) Phototoxicity of nonsteroidal antiinflammatory drugs: coincidence or specific mechanism? Arch. Dermatol. 125, 824-826.
4. Miranda, M. A. (1997) Phototoxicity of drugs, in In vitro methods in pharmaceutical research (Castell, J. V., and Gómez-Lechón, M. J., Eds.), pp 289-315, Academic Press, San Diego.
5. Cuadra-Oyanguren, J., and Navarro-Gosalbez, M. (1996) Fotosensibilidad a medicamentos en el sistema Español de farmacovigilancia, in Actas de la X Sesion Grupo Espanol de Fotobiologia (Grupo Español de Fotobiologia, Eds.) pp 22-24, ISDIN, Barcelona.
6. Moser, P., Sallmann A., and Wiesenberg, Y. (1990) Synthesis and quantitative structure-activity relationships of diclofenac analogues. J. Med. Chem. 33, 2358-2368.
7. Przybilla, B., Ring, J., Schwab, U., Galosi, A., Dorn, M., and Braun-Falco, O. (1987) Photosensibilisierende Eigenschaften Nichtsteroidaler Antirheumatika im Photopatch-test. Hautarz 38, 18-25.
8. Ljunggren, B., and Lundberg, K. (1985) In vivo phototoxicity of nonsteroidal antiinflammatory drugs evaluated by the mouse tail technique. Photodermatology 2, 377-382.
9. Ljunggren, B. (1985) Propionic acid-derived nonsteroidal antiinflammatory drugs are phototoxic in vitro. Photodermatology 2, 3-9.
10. Przybilla, B., Schwab-Przybilla, U., Ruzicka T., and Ring, J. (1987) Phototoxicity of nonsteroidal antiinflammatory drugs demonstrated in vitro by a photobasophil-histamine-release test. Photodermatology 4, 73-78.
11. Moore, D. E., Roberts-Thomson, S., Zhen, D., and Duke, C. C. (1990) Photochemical studies on the antiinflammatory drug diclofenac. Photochem. Photobiol. 52, 685-690.
12. Bosca, F., Encinas, S., Heelis, P. F., and Miranda, M. A.(1997) Photophysical and photochemical characterization of a photosensitizing drug: A combined steady-state photolysis and laser flash photolysis study on carprofen. Chem. Res. Toxicol. 10, 820-827.
13. Braun, A. M., Maurette, M.-T., and Oliveros, E. (1986) Radiométrie et Actinométrie: Actinométrie, in Technologie Photochimique (Première ed.), pp 68-72, Presses Polytechniques Romandes, Lausanne, Switzerland.
14. Molina, P., Fresneda, P. M., and Almendros, P. (1993) Fused carbazoles by tandem aza Wittig/electrocyclic ring closure. Preparation of 6H-pyrido[4,3-b]carbazole, 11H-pyrido[4,3-a]carbazole and 11H-pyrido[3,4-a]carbazole derivatives. Tetrahedron 49, 1223-1236.
15. Li, M., Larter, S. R., and Stoddart, D. (1992) Liquid Chromatographic separation schemes for pyrrole and pyridine nitrogen aromatic heterocycle fractions from crude oils suitable for rapid characterization of geochemical samples. Anal. Chem, 64, 1337-1344.
16. Miranda, M. A., Boscá, F., Vargas, F., and Canudas, N. (1994) Photosensitization by fenofibrate. II. In vitro phototoxicity of the major metabolites. Photochem. Photobiol. 59, 171-174.
17. Recknagel, R. O.; Glende, E. A., Jr. (1984) Spectrophotometric detection of lipid conjugated dienes, in Oxygen Radicals in Biological Systems. Methods in Enzymology (Packer, L., Eds.), Vol. 105, pp 331-337, Academic Press, New York.
18. Martin, M., Bréhéret, E., Tfibel, F., and Lacourbas, B. (1980) Twophoton stepwise dissociation of carbazole in solution. J. Phys. Chem. 84, 70-72.
19. Leyva, E., Platz, M. S., Niu, B., and Wirz, J. (1987) Arylaminyl radicals studied by laser flash photolysis of di-tert-butyl peroxide in the presence of arylamines. J. Phys. Chem. 91, 2293-2298.
20. Bensasson, R. V., Land, E. J., and Truscott, T. G. (1983) Flash Photolysis and Pulse Radiolysis (1st ed.), Chapter 9, pp 185-208, Pergamon Press, Oxford, England.
21. Adams, J. E., Mantulin, W. W., and Huber, J. R. (1973) Effect of molecular geometry on spin-orbit coupling of aromatic amines in solution. Diphenylamine, iminobibenzyl, acridan and carbazole. J. Am. Chem. Soc. 95, 5477-5481.
22. Weast, R. C., Astle, M. J., and Beyer, W. H. (1986-1987) Handbook of Chemistry and Physics (67th ed.), pp F:178-179, CRC Press, Boca Raton.
23. Soumillion, J. P., and Wolf, B. D. (1981) A link between photoreduction and photosubstitution of chloroaromatics compounds. J. Chem. Soc., Chem. Commun. 58, 436-437.
24. Freeman, P. K., Ramnath, N., and Richardson, A. D. (1991) Photochemistry of polyhaloarenes. 8. The photodechlorination of pentachlorobenzene. J. Org. Chem. 56, 3643-3646.
25. Boscá, F., Miranda, M. A., Carganico, G., and Mauleón, D. (1994) Photochemical and photobiological properties of ketoprofen associated with the benzophenone chromophore. Photochem. Photobiol. 60, 96-101.
26. .- radical anions in DMSO solution. J. Am. Chem. Soc. 116, 904-908.
27. Shizuka, H., Takayama, Y., Tanaka I., and Morita, T. (1970) Kinetics and mechanism of the photocyclization of diphenylamines. I. The photochemical primary processes of diphenylamines. J. Am. Chem. Soc. 16, 7270-7277.
28. Grellmann, K.-H., Kühnle, W., Weller H., and Wolff, T. (1981) The photochemical formation of dihydrocarbazoles from diphenylamines and their thermal rearrangement and disproportionation reactions. J. Am. Chem. Soc. 103, 6889-6893.
29. Epling, G. A., Black. C., and Rawal, V. (1983) Photochemistry in micelles as a model for the in vivo phototoxicity of chlorpromazine. J. Chem. Soc., Perkin Trans. 2, 1313-1316.
30. Rosenthal, Y., Ben-Hur, E., Prager, A., and Riklis, E. (1978) Photochemical reactions of chlorpromazine; chemical and biochemical implications. Photochem. Photobiol. 28, 591-594.
31. García, C., Smith, G. A., McGimpsey, W. G., Kochevar, I. E., and Redmond, R. W. (1995) Mechanism and solvent dependence for photoionization of promazine and chlorpromazine. J. Am. Chem. Soc. 117, 10871-10878.
32. Ahmad, A., and Durocher, G. (1981) How hydrogen bonding of carbazole to ethanol affects its fluorescence quenching rate by electron acceptor quencher molecules. Photochem. Photobiol. 34, 573-578.