Topical nonsteroidal antiinflammatory drugs: allergic and photoallergic contact dermatitis and phototoxicity

Ophaswongse, Suwirakorn; Maibach, Howard I.

doi:10.1111/j.1600-0536.1993.tb03483.x

Cited by 109 publications

(60 citation statements)

References 49 publications

(28 reference statements)

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“…Literatürde etofenamata bağlı tanımlanmış irritan kontakt dermatit bulunmazken allerjik ve fotoallerjik kontakt dermatit birçok kez bildirilmiştir (1,(5)(6)(7)(8). Hatta bir çalışmada etofenamat aril propiyonik asit derivelerinden (deksketoprofen, ketoprofen) sonra ikinci en sık kontakt dermatit ve fotoallerjik kontakt dermatit yapan NSAİİ olarak gösterilmiştir (8).…”

Section: Sayın Editör;unclassified

Topikal Etofenamat Kullanımına Bağlı Allerjik Kontakt Dermatit Olgusu

...

2012

Tftr

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Section: Sayın Editör;unclassified

Topikal Etofenamat Kullanımına Bağlı Allerjik Kontakt Dermatit Olgusu

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2012

Tftr

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“…In particular, the nonsteroidal antiinflammatory 2-arylpropionic acids deserve special attention because they induce such disorders more frequently than other types of drugs [4][5][6]. Tiaprofenic acid (TPA) is a member of this family, that has been found to be one of the most potent photosensitizers in a multicenter photopatch test trial [5,6].…”

Section: A Model Group Of Drugs For Photosensitization Studiesmentioning

confidence: 99%

Photosensitization by drugs

Miranda

2001

Pure and Applied Chemistry

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Certain drugs are known to elicit photosensitivity side effects. A satisfactory understanding of the involved mechanistic aspects is necessary to anticipate the photosensitizing potential. We have used tiaprofenic acid (TPA), a photosensitizing nonsteroidal antiinflammatory drug, to illustrate the methodology followed to address this problem. After studying the photophysical and photochemical properties of TPA, the attention has been directed towards the reactivity of its lowest lying π−π* triplet with biomolecules. Photosensitized lipid peroxidation occurs by a mixed type I (radicals) and type II (singlet oxygen) mechanism. In the case of proteins, the photosensitized reactions include Tyr, Trp, and His photodegradation, protein-protein photocrosslinking and drug-protein photobinding. This involves direct quenching of the drug triplet by the amino acid residues (Tyr and Trp) or by oxygen, followed by singlet oxygen oxidation (His and Trp). With DNA, the studies have included comet assay, induction of single-strand breaks in supercoiled DNA, and reaction with 2'-deoxyguanosine and thymidine. Product studies, together with time-resolved measurements, have shown that the fastest reaction occurs with purine bases, by a mechanism involving both radical and singlet oxygen processes. The employed methodology can be of general use to investigate the mechanistic aspects of photosensitization by drugs. PHOTOSENSITIVITY SIDE EFFECTSThe combined action of drugs and sunlight on patients can produce both desired and undesired effects [1]. Thus, PUVA-therapy (psoralenes plus UVA-radiation) has long been employed for the treatment of psoriasis, while porphyrins are currently being introduced for the photodynamic therapy (PDT) of cancer or other diseases. By contrast, there is also a significant number of reports indicating that a variety of drugs can elicit undesired side effects, such as phototoxicity, photoallergy, or photocarcinogenicity [2,3].The photobiological risk associated with the use of drugs depends on environmental and individual factors (climate, height on the sea level, type of skin, etc.). On the other hand, the photosensitizing potential is enhanced in the case of topically administered drugs or when the field of application is dermatology or ophthalmology. Considering all these factors, in a number of cases it may be advisable to evaluate the photobiological risk of a new drug candidate before its introduction in the market [3]. The mechanistic approach to risk predictionIn order to anticipate the appearance of photosensitivity side effects, a mechanistic understanding of the involved phenomena is necessary. Absorption of sunlight by drugs leads to their excited states. These can proceed further to afford drug-derived reactive intermediates or, under aerobic conditions, reactive oxygen species. Any of the above short-lived chemical entities may be able to interact with biological *Lecture presented at the

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“…Numerous reports document phototoxic and photoallergic contact dermatitis from systemic piroxicam, tiaprofenic acid, ketoprofen, carprofen and benoxaprofen [17]. NSAIDs that are structurally related to propionic acid have been shown to possess phototoxic potential, whereas certain other types of NSAIDs, such as piroxicam, were not experimentally phototoxic but demonstrated clinical photosensitivity [17]. However, Sugiura et al [18] carried out photopatch testing with ketoprofen on 335 patients and found there was only 1 case with a positive reaction.…”

mentioning

confidence: 99%

“…The mechanism of photosensitivity of topical NSAIDs is still not clearly defined [16,17]. Numerous reports document phototoxic and photoallergic contact dermatitis from systemic piroxicam, tiaprofenic acid, ketoprofen, carprofen and benoxaprofen [17]. NSAIDs that are structurally related to propionic acid have been shown to possess phototoxic potential, whereas certain other types of NSAIDs, such as piroxicam, were not experimentally phototoxic but demonstrated clinical photosensitivity [17].…”

mentioning

confidence: 99%

“…The 25 control cases were not photopatch tested either, so possible cases of photoallergic contact hypersensitivity to ketoprofen or etofenamate would be lost [12,16]. The mechanism of photosensitivity of topical NSAIDs is still not clearly defined [16,17]. Numerous reports document phototoxic and photoallergic contact dermatitis from systemic piroxicam, tiaprofenic acid, ketoprofen, carprofen and benoxaprofen [17].…”

mentioning

confidence: 99%

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