Chapter 17 Drug-induced skin phototoxicity: lessons from the fluoroquinolones

Comprehensive Series in Photosciences

Volumn 3, Issue C, 2001, Pages 337-356

  Gibbs, Neil K ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 58349118562     PISSN: 1568461X     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1568-461X(01)80052-1     Document Type: Chapter

References (97)

1. Pathak M.A., and Fitzpatrick T.B. The evolution of photochemotherapy with psoralens and UVA (PUVA): 2000 BC to 1992 AD. J. Photochem. Photobiol. B: Biol. 14 (1992) 3-22
2. Klaber R. Phyto-photo-dermatitis. Br. J. Dermatol. Syph. 54 (1942) 193-211
3. Kuske H. Experimentelle Untersuchungen zur Photosensibilisierung der Haut durch pflanzliche Wirkstoffe I: Lichtsensibilisierung durch Furocoumarine als Ursache verschiedener phytogener. Dermatosen. Arch. Dermatol Syphilol. 178 (1938) 112-123
4. El Mofty A.M. A preliminary clinical report on the treatment of leucodermia with Ammi majus Linn. J. R. Egyptian Med. Assoc. 31 (1948) 651-665
5. Parrish J.A., Fitzpatrick T.B., Tanenbaum L., and Pathak M.A. Photochemotherapy of psoriasis with oral methoxalen and longwave ultraviolet light. New Engl. J. Med. 291 (1974) 1207-1211
6. Raab O. Ober die Wirkung fluorescienrenden stoffe auf infusioreren. Z. Biol 39 (1900) 524-546
7. Prime J. Des accidents toxiques produit par l'eosinate du sodium. Thesis (1900), Jouve et Boyer, Paris
8. Meyer-Betz F. Untersuchungen über die biologische (photodynamische) Wirkung des Hämatopophyrins und anderer Derivative des Blut- und Gallenfarbstoffs. Dtsch. Arch. Klin. Med. 112 (1913) 476-503
9. Epstein S. Photoallergy and primary photosensitivity to sulfanilamide. J. Invest. Dermatol. 2 (1939) 43-51
10. Johnson B.E., and Fergsuon J. Drug and chemical photosensitivity. Semin. Dermatol. 9 (1990) 39-46
11. Hawk J.L.M. Photosensitizing agents used in the United Kingdom. Clin. Exp. Dermatol. 9 (1984) 300-302
12. Rosen C. Photo-induced drug eruptions. Semin. Dermatol. 8 (1991) 149-157
13. In: Spinelli P., and Dal Fante M. (Eds). Photodynamic Therapy and Biomedical Lasers (1992), Excerpta Medica, Amsterdam
14. Johnson B.E. Photomedicine: photodermatology. In: Valenzeno D.P., Pottier R.H., Mathis P., and Douglas R.H. (Eds). Photobiological Techniques (1991), Plenum, New York 323-329
15. Beijersbergen van Henegouwen G.M.J. (Systemic) phototoxicity of drugs and other xenobiotics. J. Photochem. Photobiol. B: Biol. 10 (1991) 183-210
16. Wilkinson D.S. Photodermatitis due to tetrachlorosalicylanilide. Br. J. Dermatol. 73 (1961) 213-219
17. Parker R.D., Buehler E.V., and Newman E.A. Phototoxicity, photoallergy and contact photosensitization of nitro musk perfume raw materials. Contact Dermatitis 14 (1986) 103-109
18. Kaidbey K.H., and Kligman A.M. Photocontact allergy due to 6-methylcoumarin. Contact Dermatitis 4 (1978) 277-282
19. Giudici P.A., and Maguire H.C. Experimental photoallergy to systemic drugs. J. Invest. Dermatol. 85 (1985) 207-211
20. Harber L.C., Kochevar I.E., and Shalita A.R. Mechanisms of photosensitization to drugs in humans. In: Regan J.D., and Parrish J.A. (Eds). The Science of Photomedicine (1982), Plenum, New York 323-347
21. Wolfson J.S., Hooper D.C., and Swartz M.N. Mechanisms of and resistance to quinolone antimicrobial agents. In: Wolfson J.S., and Hooper D.C. (Eds). Quinolone Antimicrobial Agents (1989), Am. Soc. Microbiol., Washington
22. Shen L.L. Do quinolones bind to DNA?-Yes. Biochem. Pharmacol. 38 (1989) 2042-2044
23. Ouedraogo G., Morliere P., Bazin M., Santus R., Kratzer B., Miranda M.A., and Castell J.V. Lysosomes are sites of fluoroquinolone photosensitization in human skin fibroblasts: a microspectrofluorometric approach. Photochem.-Photobiol. 70 (1999) 123-129
24. Zelickson A.S. Phototoxic reaction with nalidixic acid. J. Am. Med. Assoc. 190 (1964) 164-165
25. Susskind W., and Lyell A. Suspected reactions to nalidixic acid. Br. Med. J. i (1965) 316
26. Baes H. Photosensitivity caused by nalidixic acid. Dermatologica 136 (1968) 61-64
27. Burry J.N. Persistent phototoxicity due to nalidixic acid. Arch. Dermatol. 109 (1974) 263
28. Ramsey C.A., and Obreshkova E. Photosensitivity from nalidixic acid. Br. J. Dermatol. 91 (1974) 523-528
29. Keane J.T., Pearson R.W., and Malkinson F.D. Nalidixic acid-induced photosensitivity in mice: a model for pseudo porphyria. J. Invest. Dermatol. 82 (1984) 210-213
30. Birkett D.A., Garretts M., and Stevenson C.J. Phototoxic bullous eruptions due to nalidixic acid. Br. J. Dermatol. 81 (1969) 342-344
31. Brauner G.J. Bullous photoreaction to nalidixic acid. Am. J. Med. 58 (1975) 576-580
32. Lebel M., Valee F., and Bergeron M.G. Tissue penetration of Ciprofloxacin after single and multiple doses. Antimicrob. Agents Chemother. 29 (1986) 501-505
33. Arcieri G., Griffith E., Gruenwaldt G., Heyd A., O'Brien B., Becker N., and August R. Ciprofloxacin: an update on clinical experience. Am. J. Med. 82 Suppl. 4A (1987) 381-386
34. Jensen T., Pederson S.S., Nielson C.H., Hoiby N., and Koch C. The efficacy and safety of ciprofloxacin and ofloxacin in chronic Pseudomonas aeruginosa infection in cystic fibrosis. J. Antimicrob. Chemother. 20 (1987) 585-594
35. Swedish Study Group. Therapy of acute and chronic Gram-negative osteomyelitis with ciprofloxacin. J. Antimicrob. Chemother. 22 (1988) 221-228
36. Ferguson J., and Johnson B.E. Ciprofloxacin-induced photosensitivity: in vitro and in vivo studies. Br. J. Dermatol. 123 (1990) 9-20
37. Ferguson J., McEwen J., Al-Ajmi H., Purkins L., Colman P.J., and Willavize S.A. A comparison of the photosensitizing potential of trovafloxacin with that of other quinolones in healthy subjects. J. Antimicrob. Chemother. 45 (2000) 503-509
38. Shelley E.D., and Shelley W.B. The subcorneal pustular drug eruption: an example induced by Norfloxacin. Cutis 42 (1988) 24-27
39. Ferguson J., and Johnson B.E. Clinical and laboratory studies of the photosensitizing potential of norfloxacin, a 4-quinolone broad-spectrum antibiotic. Br. J. Dermatol. 128 (1993) 285-295
40. Davey P.G. Post-marketing surveillance of the quinolones: a view from Great Britain. Rev. Infect. Dis. 2 (1989) S1402-S1407
41. Scheife R.T., Cramer W.R., and Becker R.T. Photosensitizing potential of ofloxacin. Int. J. Dermatol. 32 (1993) 413-416
42. Klimberg I.W., Cox C.E., Fowler C.L., King W., Kim S.S., and Callery-D'Amico S. A controlled trial of levofloxacin and lomefloxacin in the treatment of complicated urinary tract infection. Urology 51 (1998) 610-615
43. Arata J., Horio T., Soejima R., and Ohara K. Photosensitivity reactions caused by lomefloxacin hydrochloride: a multicenter survey. Antimicrob. Agents Chemother. 42 (1998) 3141-3145
44. Traynor N.J., Barratt M.D., Lovell W.W., Ferguson J., and Gibbs N.K. Comparison of an in vitro cellular photoxicity model against controlled clinical trials of fluoroquinolone skin photoxicity. Toxicol. In Vitro 14 (2000) 275-283
45. Man I., Murphy J., and Ferguson J. Fluoroquinolone phototoxicity: a comparison of moxifloxacin and lomefloxacin in normal volunteers. J. Antimicrob. Chemother. 43 Suppl. B (1999) 77-82
46. Man I., Traynor N.J., and Ferguson J. Recent developments in fluoroquinolone photoxicity. Photodermatol. Photoimmunol. Photomed. 15 (1999) 32-33
47. Young A.R., Fakouhi T.D., Harrison G.I., Roniker B., Swabb E.A., and Hawk J.L. The UVR wavelength dependence for lomefloxacin photosensitization of human skin. J. Photochem. Photobiol. B: Biol. (1996) 165-170
48. Lowe N.J., Fakouhi T.D., Stern R.S., Bourget T., Roniker B., and Swabb E.A. Photoreactions with a fluoroquinolone antimicrobial: evening versus morning dosing. Clin. Pharmacol. Ther. 56 (1994) 587-591
49. Henry D., Ellison W., Sullivan J., Mansfield D.L., Magner D.J., Dorr M.B., and Talbot G.H. Treatment of community-acquired acute uncomplicated urinary tract infection with sparfloxacin versus ofloxacin. The Sparfloxacin Multi Center UUTI Study Group. Antimicrob. Agents Chemother. 42 (1998) 2262-2266
50. Lipsky B.A., Dorr M.B., Magner D.J., and Talbot G.H. Safety profile of sparfloxacin, a new fluoroquinolone antibiotic. Clin. Ther. 21 (1999) 148-159
51. Pierfitte C., Royer R.J., Moore N., and Begaud B. The link between sunshine and phototoxicity of sparfloxacin. Br. J. Clin. Pharmacol. 49 (2000) 609-612
52. Fu K.P., Lafredo S.C., and Foleno B. In vitro and in vivo antibacterial activities of levofloxacin (l-ofloxacin), an optically active isomer of ofloxacin. Antimicrob. Agents Chemother. 36 (1992) 860-866
53. North D.S., Fish D.N., and Redington J.J. Levofloxacin, a second-generation fluoroquinolone. Pharmacotherapy 18 (1998) 915-935
54. Boccumini L.E., Fowler C.L., Campbell T.A., Puertolas L.F., and Kaidbey K.H. Photoreaction potential of orally administered levofloxacin in healthy subjects. Ann. Pharmacother. 34 (2000) 453-458
55. Williams D., and Hopkins S. Safety of trovafloxacin in treatment of lower respiratory tract infections. Eur. J. Clin. Microbiol. Infect. Dis. 17 (1998) 454-458
56. Lucena M.I., Andrade R.J., Rodrigo L., Salmeron J., Alvarez A., Lopez-Garrido M.J., Camargo R., and Alcantara R. Trovafloxacin-induced acute hepatitis. Clin. Infect. Dis. 30 (2000) 400-401
57. Perry C.M., Barman J.A., Balfour J.A., and Lamb H.M. Gatifloxacin. Drugs 58 (1999) 683-696
58. Zhanel G.G., Walkty A., and Vercaigne L. The new fluoroquinolones: a critical review. Can. J. Infect. Dis. 10 (1999) 207-238
59. Vousden M., Ferguson J., Richards J., Bird N., and Allen A. Evaluation of phototoxic potential of gemifloxacin in healthy volunteers compared with ciprofloxacin. Chemotherapy 45 (1999) 512-520
60. Wagia N., and Tawara K. Important role of oxygen metabolites in quinolone antibacterial agent-induced cutaneous phototoxicity in mice. Arch. Toxicol. 65 (1991) 495-499
61. Wagai N., and Tawara K. Possible reasons for differences in phototoxic potential of a 5 quinolone antibacterial agents: generation of toxic oxygen. Free Radic. Res. Commun. 17 (1992) 387-398
62. Moore D.E., Hemens V.J., and Yip H. Photosensitization by drugs: nalidixic and oxolinic acids. Photochem. Photobiol. 39 (1984) 57-61
63. Dayhaw-Barker P., and Truscott T.G. Direct detection of singlet oxygen sensitized by nalidixic acid: the effect of pH and melanin. Photochem. Photobiol. 47 (1988) 765-767
64. Martinez L.J., Sik R.H., and Chignell C.F. Fluoroquinolone antimicrobials: singlet oxygen, superoxide and phototoxicity. Photochem. Photobiol. 67 (1998) 399-403
65. Martinez L.J., and Chignell C.F. Photogeneration of fluoride by the fluoroquinolone antimicrobial agents lomefloxacin and fleroxacin. Photochem. Photobiol. 65 (1997) 599-602
66. Fasani E., Profumo A., and Albini A. Structure and medium-dependent photodecomposition of fluoroquinolone antibiotics. Photochem. Photobiol. 68 (1998) 666-674
67. Matsumoto M., Kojima K., Nagano H., Matsubara S., and Yokota T. Photostability and biological activity of fluoroquinolones substituted at the 8 position after UV irradiation. Antimicrob. Agents Chemother. 36 (1992) 1715-1719
68. Marutani K., Matsumoto M., Otabe Y., Nagamuta M., Tanaka K., Miyoshi A., Hasegawa T., Nagano H., Matsubara S., and Kamide R. Reduced phototoxicity of a fluoroquinolone antibacterial agent with a methoxy group at the 8 position in mice irradiated with long-wavelength UV light. Antimicrob. Agents Chemother. 37 (1993) 2217-2223
69. Shimoda K., Wagai N., and Kato M. Stimulation of prostaglandin production by quinolone phototoxicity in Balb/c 3T3 mouse fibroblast cells in vitro. Fundam. Appl. Toxicol. 36 (1997) 157-162
70. Shimoda K., and Kato M. Involvement of reactive oxygen species, protein kinase C, and tyrosine, kinase in prostaglandin E2 production in Balb/c 3T3 mouse fibroblast cells by quinolone phototoxicity. Arch. Toxicol. 72 (1998) 251-256
71. Kurumaji Y., and Shono M. Scarified photopatch testing in lomefloxacin photosensitivity. Contact Dermatitis 26 (1992) 5-10
72. Tokura Y., Seo N., Ohshima A., Yagi H., Furukawa F., and Takigawa M. Lymphocyte stimulation test with drug-photomodified cells in patients, with quinolone photosensitivity. J. Dermatol. Sci. 21 (1999) 34-41
73. Horio T., Miyauchi H., Asada Y., Aoki Y., and Harada M. Phototoxicity and photoallergenicity of quinolones in guinea pigs. J. Dermatol. Sci. 7 (1994) 130-135
74. Tokura Y. Quinolone photoallergy: photosensitivity dermatitis induced by systemic administration of photohaptenic drugs. J. Dermatol. Sci. 18 (1998) 1-10
75. Kimura M., and Kawada A. Photosensitivity induced by lomefloxacin with cross-photosensitivity to ciprofloxacin and fleroxacin. Contact Dermatitis 38 (1998) 180
76. Tokura Y., Nishijima T., Yagi H., Furukawa F., and Takigawa M. Photohaptenic properties of fluoroquinolones. Photochem. Photobiol. 64 (1996) 838-844
77. Marutani K., Otabe Y., Nagamuta M., Matsubara S., and Otani H. Photoallergenicity of a fluoroquinolone antibacterial agent with a fluorine substituent at the 8-position in guinea pigs exposed to long-wavelength UV light. Skin Pharmacol. Appl. Skin. Physiol. 11 (1998) 232-240
78. Ohshima A., Seo N., Takigawa M., and Tokura Y. Formation of antigenic quinolone photoadducts on Langerhans cells initiates photoallergy to systemically administered quinolone in mice. J. Invest. Dermatol. 114 (2000) 569-575
79. Vohr H.-W., Blumel J., Blotz A., Homey B., and Ahr H.J. An intralaboratory validation of the Intergrated Model for the Differation of Skin Reactions (IMDS): discrimination between (photo)allergic and (photo)irritant skin reactions in mice. Arch. Toxicol. 73 (2000) 501-509
80. Johnson B.E., Gibbs N.K., and Ferguson J. Quinolone antibiotic with potential to photosensitize skin tumorigenesis. J. Photochem. Photobiol. B: Biol. 37 (1997) 171-173
81. Klecak G., Urbach F., and Urwyler H. Fluoroquinolone antibacterials enhance UVA-induced skin tumors. J. Photochem. Photobiol. B: Biol. 37 (1997) 174-181
82. Makinen M., Forbes P.D., and Stenback F. Quinolone antibacterials: a new class of photochemical carcinogens. J. Photochem. Photobiol. B: Biol. 37 (1997) 182-187
83. Draft Document. Food and Drug Administration. Guidance for Industry Photosafety Testing (January, 2000)
84. Traynor N.J., Reavy H.J., Lowe J.G., Ferguson J., Ananthaswamy H., and Gibbs N.K. Mechanisms of fluoroquinolone photosensitised skin tumorigenesis. Br. J. Dermatol. 142 (2000) 608-609
85. Reavy H.J., Traynor N.J., and Gibbs N.K. Photogenotoxicity of skin phototumorigenic fluoroquinolone antibiotics detected using the single cell gel electrophoresis (comet) assay. Photochem. Photobiol. 66 (1997) 368-373
86. Bulera S.J., Theis J.C., Festerling T.A., and de la Iglesia F.A. In vitro photogenotoxic activity of clinafloxacin: a paradigm predicting photocarcinogenicity. Toxicol. Appl. Pharmacol. 156 (1999) 220-230
87. Chételat A., Albertini S., and Gocke E. The photomutagenicity of fluoroquinolones in tests for gene mutation, chromosomal aberration, gene conversion and DNA breakage (Comet assay). Mutagenesis 11 (1996) 497-504
88. Martínez L.J., and Chignell C.F. Photocleavage of DNA by the fluoroquinolone antibacterials. J Photochem. Photobiology B: Biol. 45 (1998) 51-59
89. 2 . Br. J. Dermatol. 140 (1999) 784
90. Klaude M.S., Eriksson S., Nygren J., and Ahnström G. The comet assay: mechanisms and technical considerations. Mutat. Res. 363 (1996) 89-96
91. Gedik C.M., Ewen S.W.B., and Collins A.R. Single-cell gel electrophoresis applied to the analysis of UVC damage and its repair in human cells. Int. J. Radiation. Biol. 62 (1992) 313-320
92. Rosen J.E., Chen D., Prahalad A.K., Spratt T.E., Schluter G., and Williams G.M. A fluoroquinolone antibiotic with a methoxy group at the 8 position yields reduced generation of 8-oxo-7,8-dihydro-2′-deoxyguanosine after ultraviolet-A irradiation. Toxicol. Appl. Pharmacol. 145 (1997) 381-387
93. Spratt T.E., Schultz S.S., Levy D.E., Chen D., Schluter G., and Williams G.M. Different mechanisms for the photoinduced production, of oxidative DNA damage by fluoroquinolones differing in photostability. Chem. Res. Toxicol. 12 (1999) 809-815
94. Ziegler A., Jonason A.S., Lelrell D.J., Sinion J.A., Shanna H.W., Kimmelman J., Reniington L., Jacks T., and Brash D.E. Sunburn and p. 53 in the onset of skin cancer. Nature 372 (1994) 773-776
95. Spielmann H., Balls M., Brand M., Döring B., Holzhütter H.G., Kalweit S., Klecak G., Eplattenier H.L., Liebsch M., Lovell W.W., Maurer T., Moldenhauer F., Moore L., Pape W.J.W., Pfanenbecker U., Potthast J., De Silva O., Steiling W., and Willshaw A. EEC/COLIPA project on in vitro phototoxicity testing: first results obtained with a BALB/c 3T3 cell photoxicity assay. Toxicol. In Vitro 8 (1994) 793-796
96. Barratt M.D., Castell J.V., Miranda M.A., and Langowski J.J. Development of an expert system rulebase for the prospective identification of photoallergens. J. Photochem. Photobiol. B: Biol. 58 (2000) 54-61
97. Barratt M.D., Castell J.V., Miranda M.A., and Langowski J.J. Development of an expert system rulebase for the prospective identification of photoallergens. J. Photochem. Photobiol. B: Biol. 58 (2000) 97