DOI: 10.1111/j.1751-1097.1988.tb02710.x. A COMPARATIVE STUDY OF THE PHOTOCHEMISTRY OF THE NON‐STEROIDAL ANTI‐INFLAMMATORY DRUGS, NAPROXEN, BENOXAPROFEN AND INDOMETHACIN

A COMPARATIVE STUDY OF THE PHOTOCHEMISTRY OF THE NON‐STEROIDAL ANTI‐INFLAMMATORY DRUGS, NAPROXEN, BENOXAPROFEN AND INDOMETHACIN

10.1111/j.1751-1097.1988.tb02710.x

Crossref journal-article

Wiley

Photochemistry and Photobiology (311)

Abstract

Abstract—The photochemical reactivity of the non‐steroidal anti‐inflammatory drugs, naproxen and indomethacin, has been studied and compared with benoxaprofen, a similar compound of known cutaneous phototoxicity. Although indomethacin shows some phosphorescence at 77 K, flash photolysis at room temperature revealed only a weak photoionization process, and no photochemical reactivity was detected in steady state photolysis. Naproxen has strong fluorescence and phosphorescence, and in laser flash photolysis showed photoionization and a triplet state species in approximately equal yield. Naproxen and benoxaprofen produced singlet oxygen with similar quantum yield, as deduced from the sensitized rates of photooxidation of 2,5‐dimethylfuran. Naproxen underwent photodecarboxylation as detected by ESR‐spin trap experiments with 2‐methyl‐2‐nitrosopropane. The decarboxy‐naproxen radical combined readily with oxygen in aerated solution, and l‐(6‐methoxy‐2‐napthyl)ethanol and 2‐acetyl‐6‐methoxynaphthalene were formed as the oxidation products. In deaer‐ated solution, the major product was 2‐ethyI‐6‐methoxynaphthalene, with the alcohol also formed. In comparison, benoxaprofen also underwent decarboxylation, with much higher quantum yield, but the decarboxy‐benoxaprofen radical did not add oxygen. This difference in photoreactivity between naproxen and benoxaprofen, together with the much lower molar absorptivity of naproxen are the significant factors in relating to the differences in reported levels of clinical photosensitivity responses.

Bibliography

MOORE, D. E., & CHAPPUIS, P. P. (1988). A COMPARATIVE STUDY OF THE PHOTOCHEMISTRY OF THE NONâSTEROIDAL ANTIâINFLAMMATORY DRUGS, NAPROXEN, BENOXAPROFEN AND INDOMETHACIN. Photochemistry and Photobiology, 47(2), 173â180. Portico.

Authors 2

DOUGLAS E. MOORE (first)
PHILLIPE P. CHAPPUIS (additional)

References 27 Referenced 113

10.1021/ja00843a004
10.1039/p19730000526
10.1111/j.1751-1097.1980.tb04023.x
10.1021/jf60166a001
Davidson R. S.andP. R.Steiner(1971)The photosensitized decarboxylation of carboxylic acids by benzo‐phenone and quinones.J. Chem. Soc. (C) 1682–1689. (10.1039/j39710001682)
10.1016/S0165-8646(24)00141-7 / Photobiochem. Photobiophys. / Photosensitivity studies and benoxaprofen by Diffey B. L. (1983)
{'key': 'e_1_2_1_8_1', 'first-page': '633', 'article-title': 'Photosensitivity studies of non‐steroidal anti‐inflammatory agents', 'volume': '16', 'author': 'Diffey B. L.', 'year': '1983', 'journal-title': 'Br. J. Rheumatol'} / Br. J. Rheumatol / Photosensitivity studies of non‐steroidal anti‐inflammatory agents by Diffey B. L. (1983)
10.1093/rheumatology/22.4.239
10.1016/B978-0-12-252850-7.50005-8
10.1111/j.1365-2133.1982.tb00386.x
10.1136/bmj.284.6326.1365
{'volume-title': 'The Science of Photomedicine', 'year': '1982', 'author': 'Harber L. C.', 'key': 'e_1_2_1_13_1'} / The Science of Photomedicine by Harber L. C. (1982)
10.1021/ja00966a017
{'key': 'e_1_2_1_15_1', 'first-page': '124', 'article-title': 'Phototoxicity to benoxaprofen', 'volume': '5', 'author': 'Kligman A. M.', 'year': '1982', 'journal-title': 'Eur. J. Rheumat. Inflamm.'} / Eur. J. Rheumat. Inflamm. / Phototoxicity to benoxaprofen by Kligman A. M. (1982)
10.1111/1523-1747.ep12260034
10.1001/archderm.1986.01660230075014 / Arch. Dermatol. / Possible mechanism of piroxicam induced photosensitivity by Kochevar I. E. (1986)
10.1111/1523-1747.ep12522659
{'key': 'e_1_2_1_19_1', 'first-page': '3', 'article-title': 'Propionic acid‐derived non‐steroidal anti‐inflammatory drugs are phototoxic in vitro', 'volume': '2', 'author': 'Ljunggren B.', 'year': '1985', 'journal-title': 'Photodermatology'} / Photodermatology / Propionic acid‐derived non‐steroidal anti‐inflammatory drugs are phototoxic in vitro by Ljunggren B. (1985)
{'key': 'e_1_2_1_20_1', 'first-page': '377', 'article-title': 'In vivo phototoxicity of non‐steroidal anti‐inflammatory drugs evaluated by the mouse tail technique', 'volume': '2', 'author': 'Ljunggren B.', 'year': '1985', 'journal-title': 'Photodermatology'} / Photodermatology / In vivo phototoxicity of non‐steroidal anti‐inflammatory drugs evaluated by the mouse tail technique by Ljunggren B. (1985)
10.1111/j.1751-1097.1981.tb09021.x
10.1111/j.1751-1097.1985.tb03501.x
{'key': 'e_1_2_1_23_1', 'first-page': '8', 'article-title': 'Nichtsteroidale Antirheumatika mit photosensibilisierender Wirkung', 'volume': '9', 'author': 'Przybilla B.', 'year': '1986', 'journal-title': 'Allergologie'} / Allergologie / Nichtsteroidale Antirheumatika mit photosensibilisierender Wirkung by Przybilla B. (1986)
10.1111/j.1751-1097.1983.tb03594.x
10.1111/j.1751-1097.1983.tb02673.x
{'key': 'e_1_2_1_26_1', 'first-page': '16', 'volume-title': 'Atmospheric Oxidation and Antioxidants', 'author': 'Scott G.', 'year': '1965'} / Atmospheric Oxidation and Antioxidants by Scott G. (1965)
{'key': 'e_1_2_1_27_1', 'first-page': '87', 'volume-title': 'The Science of Photobiology.', 'author': 'Spikes J. D.', 'year': '1977'} / The Science of Photobiology. by Spikes J. D. (1977)
{'key': 'e_1_2_1_28_1', 'first-page': '730', 'article-title': 'Photosensibilisierung durch benoxaprofen', 'volume': '31', 'author': 'Wiskman A.', 'year': '1981', 'journal-title': 'Arzneim. Forsch.'} / Arzneim. Forsch. / Photosensibilisierung durch benoxaprofen by Wiskman A. (1981)

Dates

Type	When
Created	17 years, 8 months ago (Jan. 2, 2008, 4:15 p.m.)
Deposited	7 months, 1 week ago (Jan. 24, 2025, 11:56 p.m.)
Indexed	7 months, 1 week ago (Jan. 26, 2025, 12:17 a.m.)
Issued	37 years, 7 months ago (Feb. 1, 1988)
Published	37 years, 7 months ago (Feb. 1, 1988)
Published Online	17 years, 8 months ago (Jan. 2, 2008)
Published Print	37 years, 7 months ago (Feb. 1, 1988)

Funders 0

None

BibTeX

@article{MOORE_1988, title={A COMPARATIVE STUDY OF THE PHOTOCHEMISTRY OF THE NON‐STEROIDAL ANTI‐INFLAMMATORY DRUGS, NAPROXEN, BENOXAPROFEN AND INDOMETHACIN}, volume={47}, ISSN={1751-1097}, url={http://dx.doi.org/10.1111/j.1751-1097.1988.tb02710.x}, DOI={10.1111/j.1751-1097.1988.tb02710.x}, number={2}, journal={Photochemistry and Photobiology}, publisher={Wiley}, author={MOORE, DOUGLAS E. and CHAPPUIS, PHILLIPE P.}, year={1988}, month=feb, pages={173–180} }

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