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The effect of natural sunlight on ciprofloxacin ophthalmic solution (1).

Article Excerpt
Ciprofloxacin (0.3% preparation) is available on the market for topical ophthalmic use. The marketed eye drop samples, as well as reference ciprofloxacin in aqueous solution were found to degrade to an ethylenediamine derivative of ciprofloxacin when exposed to natural sunlight. The degradation product was identified by comparison to a reference standard as well as by LC-MS, M[S.sup.2] and M[S.sup.3]. A model compound, phenylpiperazine, was found to decompose to a N-phenylethylenediamine after sunlight exposure at a much slower rate compared to ciprofloxacin. When tested against Bacillus pumillus, the sunlight exposed ophthalmic solution of ciprofloxacin showed reduction by 2.6% of antimicrobial potency in 24 hrs compared to properly stored solution. However, ciprofloxacin ophthalmic drop containers stored in original cartons, showed no HPLC detectable photolytic degradation.

Keywords: Ciprofloxacin ophthalmic solution, sunlight, photodegradation, phenylpiperazine, electrospray mass spectrometry

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Ciprofloxacin is the generic international name for the most common and widely used fluoroquinolone antibacterial agent originally introduced by Bayer Pharmaceuticals. In general, ciprofloxacin has good activity against both gram-negative and gram-positive bacteria. It is effective against a number of different types of bacteria that cause severe infections in humans, including Streptococcus pneumoniae, Staphylococcus aureus, Escherichia coli, Proteus mirabillis, Klebsiella pneumoniae and Pseudomonas aeruginosa. This antibiotic has now been released as ophthalmic drops and is useful against eye infections. When used topically, corneal toxicity and retinal toxicity rarely occur. Corneal precipitation occurs with ciprofloxacin but does not appear to interfere with healing (Smith et al., 2001).

Ciprofloxacin solution (0.3%) is currently available for topical ophthalmic use. Ciprofloxacin and ofloxacin are recognized as being safe to use, but there have been reports of skin reddening and rashes in patients taking these antibiotics after sun exposure, symptoms common to photosensitivity (The Fluoroquinolone Toxicity Research Foundation, Webpage). Research at Southmead Hospital Bristol on the stability of ciprofloxacin and ofloxacin eye drops showed that loss of antibiotic potency occurred when ciprofloxacin was irradiated at 320 nm and then tested against Escherichia coli (Tobin, Webpage; Phillips et al., 1990). On the other hand, Sunderland et al. in 1999 reported that the photo-degradation products of ofloxacin were effective in killing bacteria. In addition, initial experiments suggest that the photodegradation products may cause toxicity. There is an extensive report (Sunderland et al., 2001) on the antibiotic activity of...

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