Photosensitivity Associated with Carprofen

Roelandts, Rik

doi:10.1159/000249297

Cited by 11 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1, all of them are 2-arylpropionic acid derivatives. Unambiguous evidence of their photosensitivity side effects has been obtained at the clinical level (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21). The phototoxic reactions associated with BP, CP, NP, KP, TP and SP usually appear as an exaggerated sunburn characterized by erythema and edema.…”

Section: Introductionmentioning

confidence: 99%

“…Hyperpigmentation is also a relatively common sequela of phototoxicity, and it may persist for several months. Moreover, some of these drugs are able to mediate special forms of phototoxicity, such as photoonycholysis which has been observed with BP and pseudoporphyria, associated with BP, NP and TP (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13). In the case of CP, KP, TP and SP, most of the reported effects have been associated with photoallergy (13)(14)(15)(16)(17)(18)(19)(20).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Photoreactivity of the Nonsteroidal Anti-inflammatory 2-Arylpropionic Acids with Photosensitizing Side Effects¶

Boscá

Marín

Miranda

2007

Photochemistry and Photobiology

View full text Add to dashboard Cite

The photoreactivity of the nonsteroidal anti-inflammatory 2-arylpropionic acids benoxaprofen, carprofen, naproxen, ketoprofen, tiaprofenic acid, and suprofen is reviewed with special emphasis on fundamental photophysical and photochemical properties. The absorption and emission properties of the excited states of these drugs as well as their main photodegradation routes are summarized. The photochemical mechanisms are discussed on the basis of product studies and detection of short-lived intermediates by means of laser flash photolysis. After dealing with the unimolecular processes, attention is focused on the photosensitized reactions of key biomolecules, such as lipids, proteins or nucleic acids. Finally, a short section on the photobiological effects on simple biological models is also included. Although some earlier citations are included, the literature coverage is in general limited to the last decade.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoreactivity of the Nonsteroidal Anti-inflammatory 2-Arylpropionic Acids with Photosensitizing Side Effects¶

Boscá

Marín

Miranda

2007

Photochemistry and Photobiology

View full text Add to dashboard Cite

show abstract

“…Several nonsteroidal anti-inflammatory 2-arylpropionic acids have shown an unusual potential to induce photosensitivity disorders (1)(2)(3)(4). In this context, a number of case reports have appeared on photosensitization by carprofen (1a) (5)(6)(7)(8), which have been reproduced by means of photopatch tests studies (9). Thus, a multicenter trial performed with more than 1000 patients showed that (out of 32) carprofen was the third most potent test chemical according to the incidence of phototoxic as well as photoallergic reactions (9).…”

Section: Introductionmentioning

confidence: 99%

Photophysical and Photochemical Characterization of a Photosensitizing Drug: A Combined Steady State Photolysis and Laser Flash Photolysis Study on Carprofen

Boscá

Encinas

Heelis

et al. 1997

Chem. Res. Toxicol.

View full text Add to dashboard Cite

Carprofen (1a) is a photosensitizing nonsteroidal anti-inflammatory drug. It undergoes photodehalogenation from its triplet excited state. The resulting aryl radical (II) is able to abstract hydrogen atoms from model lipids, mediating their peroxidation by a type I mechanism. This aryl radical intermediate appears to be responsible for the observed photobiological effects of carprofen. The active involvement of the triplet state has been confirmed by direct detection of this species in laser flash photolysis and by quenching experiments with cyclohexadiene and naphthalene. Carprofen also photosensitizes singlet oxygen production with a quantum yield of 0.32. A minor reaction pathway is photodecarboxylation, which occurs from the excited singlet state and leads to an acetyl derivative (1b). In the case of the dehalogenated photoproduct (2a), photodecarboxylation to the ethyl (2d) and acetyl (2b) derivatives, together with singlet oxygen production (quantum yield = 0.18), is also possible. However, the biological activity of 2a in the linoleic acid photoperoxidation and photohemolysis tests is markedly lower than that of 1a, which constitutes further evidence in favor of the important role of photodehalogenation in the adverse photobiological effects of carprofen.

show abstract

“…56 Carprofen is a photosensitizing drug and reports of phototoxic and photoallergic contact dermatitis may have precipitated the situation further. 57,58 It was reintroduced in several parts of the world under various trade names (Rimadyl, Norocarp, etc.) as pain-relieving medication for veterinary treatment.…”

Section: Ibuprofenmentioning

confidence: 99%

Repurposing drugs for treatment of tuberculosis: a role for non-steroidal anti-inflammatory drugs

et al. 2016

View full text Add to dashboard Cite

show abstract

Photosensitivity Associated with Carprofen

Cited by 11 publications

References 0 publications

Photoreactivity of the Nonsteroidal Anti-inflammatory 2-Arylpropionic Acids with Photosensitizing Side Effects¶

Photoreactivity of the Nonsteroidal Anti-inflammatory 2-Arylpropionic Acids with Photosensitizing Side Effects¶

Photophysical and Photochemical Characterization of a Photosensitizing Drug: A Combined Steady State Photolysis and Laser Flash Photolysis Study on Carprofen

Repurposing drugs for treatment of tuberculosis: a role for non-steroidal anti-inflammatory drugs

Contact Info

Product

Resources

About