Photoonycholysis Induced by the Fluoroquinolones Pefloxacine and Ofloxacine

Baran, Robert; Brun, Patrick

doi:10.1159/000249247

Cited by 55 publications

(10 citation statements)

References 2 publications

(2 reference statements)

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“…Furthermore, clinical development of photosensitivity has been noticed in chemotherapy with fluoroquinolone antibacterial agents, especially with LFLX (2,9,11,12,23). In fact, some clinical cases suggest that the LFLXinduced photodermatosis occurs not only as an allergic toxicity via the immune system but also as a primary toxic reaction (9).…”

Section: Resultsmentioning

confidence: 99%

Reduced phototoxicity of a fluoroquinolone antibacterial agent with a methoxy group at the 8 position in mice irradiated with long-wavelength UV light

Marutani¹,

Matsumoto²,

Otabe³

et al. 1993

Antimicrob Agents Chemother

109

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A newly developed fluoroquinoline, Q-35 (8-OCH3), in which a methoxy group was substituted at the 8 position of the quinoline nucleus, was very stable under irradiation with long-wave UV light (UVA). Derivatives, a fluoroquinolone with no substitution (the 8-H analog) and one in which a fluorine was substituted (the 8-F analog), were degraded in their solutions by the UVA irradiation. The phototoxic inducibility by these derivatives was further studied in a murine model. When mice were dosed orally with 800 mg of Q-35 (8-OCH3) per kg of body weight, the maximum dose given, and exposed to the UVA light, no inflammatory lesions were observed in their ears. Ear redness was marked in mice given more than 12.5 mg of the 8-F analog or 200 mg of the 8-H analog per kg. Histopathological changes, edema, and infiltration of neutrophils were also observed microscopically in groups receiving the 8-H or 8-F analog but not in groups receiving Q-35 (8-OCH3). Similar inflammatory reactions were observed to occur in a dose-dependent manner with other available fluoroquinolone antibacterial agents such as lomefloxacin, enoxacin, norfloxacin, ciprofloxacin and ofloxacin. These results suggest that the introduction of a methoxy group at the 8 position of the quinolone nucleus is important for the reduction of phototoxicity.

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Section: Resultsmentioning

confidence: 99%

Reduced phototoxicity of a fluoroquinolone antibacterial agent with a methoxy group at the 8 position in mice irradiated with long-wavelength UV light

Marutani¹,

Matsumoto²,

Otabe³

et al. 1993

Antimicrob Agents Chemother

109

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“…As a matter of fact, NA is clinically known as a photosensitizer (1,3,4), and the photosensitivities of some of fluoroquinolone antibiotics that are on the market have also been reported (2,5,13,14). In order to compare the phototoxicity potentials of these quinolone antibiotics, Wagai et al (21) investigated UVA irradiation (21.6-J/cm2)-induced erythema as a biological marker; the erythema occurs in the ears of mice after oral administration of NA.…”

Section: Discussionmentioning

confidence: 99%

Photostability and biological activity of fluoroquinolones substituted at the 8 position after UV irradiation

Matsumoto¹,

Kojima²,

Nagano³

et al. 1992

Antimicrob Agents Chemother

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Q-35 [1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylaminopiperidine-1-yl)-4-oxoquinoline-3-carboxylic acid], a fluoroquinolone, has absorbance peaks at 333 and 286 nm. No spectral change was observed even when this aqueous solution was irradiated with 3 J of long-wavelength UV light (UVA) per cm2. On the other hand, its derivatives, which are unsubstituted (8-H analog) or which are substituted with fluorine at the 8 position (8-F analog), were found to have decreased antibacterial activities with a simultaneous increase in their cytotoxicities when they were degraded in a dose-dependent manner with respect to UVA irradiation. Similar results were observed with the other available fluoroquinolones. Enoxacin and lomefloxacin exposed to 0.3 J of irradiation per cm2 and norfloxacin, ofloxacin, and ciprofloxacin exposed to 1 J of irradiation per cm2 underwent absorption spectrum changes, an accompanying decrease in antibacterial activity, and an increase in cytotoxic activity. These results suggest that the introduction of a methoxy group into the 8 position of quinolones plays an important role in the stability of fluoroquinolones against irradiation by UV light.

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“…In contrast to this, clinical photosensitivity reactions in association with the administration of quinolones other than nalidixic acid have been reported only rarely [16][17][18][19][20]. This could point to a lack of a prominent photosensitizing potential in vivo.…”

Section: Discussionmentioning

confidence: 99%

“…In recent years several new, 'second-generation' antibacterial agents of this pharmacological class have become available for therapy and are gaining increasing importance [15]. During the administration of such new quinolones, photo-onycholy sis [16,17] and photo-dependent drug eruptions [18][19][20] occurred in a few cases, and a reduction of the minimal erythema dose for UVA was reported [211.We screened a number o f'first-' and 'second-generation' quinolones for phototoxic properties in a hemolysis test. Eight of 10 compounds tested exhibited phototoxic effects.…”

mentioning

confidence: 99%

Demonstration of Quinolone Phototoxicity in vitro

Przybilla

Georgii²,

Bergner³

et al. 1990

Dermatology

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The ‘first-generation’ quinolones cinoxacin, nalidixic acid, oxolinic acid, pipemidic acid and rosoxacin and the newly developed quinolones ciprofloxacin, enoxacin, fleroxacin, norfloxacin and ofloxacin were screened in vitro at 10^––⁵,10^––4 and 10^––3M concentrations for ultraviolet (UV)-induced phototoxic effects in a photohemolysis test. At 10^––3 M, photodependent effects of norfloxacin could not be evaluated, as hemolysis occurred without irradiation. All other compounds with the exception of ciprofloxacin were found to be phototoxic at 10^-3 M and some also at 10^-4M. Hemolysis was UV dose dependent and for all compounds most prominent after exposure to UVA-rich radiation except for fleroxacin which was most active in the UVB range. Besides fleroxacin, also oxolinic acid, pipemidic acid and rosoxacin induced hemolysis with irradiations rich in UVB. It is concluded that quinolones have to be regarded as potentially phototoxic substances. Therefore intense light exposure should be avoided during treatment with these agents.

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Photoonycholysis Induced by the Fluoroquinolones Pefloxacine and Ofloxacine

Abstract: Pefloxacine and ofloxacine are 2 new synthetic fluoroquinolones which should be added to the list of drugs inducing photoonycholysis. Two cases are reported.

Cited by 55 publications

References 2 publications

Reduced phototoxicity of a fluoroquinolone antibacterial agent with a methoxy group at the 8 position in mice irradiated with long-wavelength UV light

Reduced phototoxicity of a fluoroquinolone antibacterial agent with a methoxy group at the 8 position in mice irradiated with long-wavelength UV light

Photostability and biological activity of fluoroquinolones substituted at the 8 position after UV irradiation

Demonstration of Quinolone Phototoxicity in vitro

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