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酮洛芬、舒洛芬、噻洛芬酸和二苯甲酮的光毒性、光敏化潜力及豚鼠体内光交叉反应性的实验研究

Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs.

作者信息

Sugiura Mariko, Hayakawa Ritsuko, Xie Zhenlin, Sugiura Keiji, Hiramoto Keiichi, Shamoto Mikihiro

机构信息

Department of Environmental Dermatology, Nagoya University School of Medicine, Japan.

出版信息

Photodermatol Photoimmunol Photomed. 2002 Apr;18(2):82-9. doi: 10.1034/j.1600-0781.2002.180205.x.

Abstract

BACKGROUND

Ketoprofen, suprofen and tiaprofenic acid are arylpropionic anti-inflammatories. Their chemical structures share the same elements as the benzoyl radical and the tiophene ring. We experienced nine cases of ketoprofen photoallergy, seven cases of suprofen photoallergy and three cases of tiaprofenic photoallergy.

PURPOSE

To find the key structure of photosensitivity and photocross-reactivity to ketoprofen, suprofen and tiaprofenic acid.

METHODS

: Three animals were tested for phototoxicity and six animals for the photosensitization potentials of ketoprofen, suprofen, tiaprofenic acid and benzophenone, and the photocross-reactivity of the above chemicals. Test substances were applied symmetrically on both sides of the animals' backs. The animals were irradiated with 180 mJ/cm2 UVB ((1/2) MED) and 10 J/cm2 UVA on the left side. The reactions were read on days 2, 3 and 4. The photosensitization potentials of ketoprofen, suprofen, tiaprofenic acid and benzophenone were determined using the Adjuvant-Strip method. Six animals were assigned to each test group and to a control group.

RESULTS

Ketoprofen, suprofen, tiaprofenic acid and propionic acid showed negative reactions with the phototoxic test. Benzophenone showed phototoxic reactions to 40% acetone (ac.), 20% ac. and 10% ac. Therefore, we used 5% aq. benzophenone with the photosensitization test. Ketoprofen was the strongest photosensitizer (6/6) and showed photocross-reactivities to suprofen (2/6), tiaprofenic acid (3/6) and benzophenone (6/6). Suprofen was a strong photosensitizer (4/6) and showed photocross-reactivities to ketoprofen (1/4) and tiaprofenic acid (2/4), but not to benzophenone. Tiaprofenic acid was also a photosensitizer (2/6) but showed a photocross-reactivity only to benzophenone (2/2). Benzophenone was also the strongest photosensitizer (6/6), but did not photocross-react to the above three chemicals.

CONCLUSION

From the test results, it appears that benzoyl radical is the key structure for photosensitivity and the photocross-reactivity of ketoprofen, suprofen and tiaprofenic acid. The whole structure of benzophenone was needed to induce photosensitization of benzophenone. The animals that were photosensitized from the entire structure of benzophenone did not photocross-react to ketoprofen, suprofen or tiaprofenic acid.

摘要

背景

酮洛芬、舒洛芬和噻洛芬酸均为芳基丙酸类抗炎药。它们的化学结构与苯甲酰基和噻吩环具有相同的元素。我们遇到了9例酮洛芬光过敏病例、7例舒洛芬光过敏病例和3例噻洛芬酸光过敏病例。

目的

寻找酮洛芬、舒洛芬和噻洛芬酸光敏性及光交叉反应性的关键结构。

方法

对3只动物进行光毒性测试,对6只动物进行酮洛芬、舒洛芬、噻洛芬酸和二苯甲酮的光敏性潜力以及上述化学物质的光交叉反应性测试。将受试物质对称涂抹于动物背部两侧。左侧用180 mJ/cm² 中波紫外线((1/2)最小红斑量)和10 J/cm² 长波紫外线照射动物。在第2、3和4天观察反应。采用佐剂条法测定酮洛芬、舒洛芬、噻洛芬酸和二苯甲酮的光敏性潜力。每个测试组和对照组分配6只动物。

结果

酮洛芬、舒洛芬、噻洛芬酸和丙酸在光毒性测试中呈阴性反应。二苯甲酮对40%丙酮、20%丙酮和10%丙酮表现出光毒性反应。因此,我们在光敏性测试中使用5%的二苯甲酮水溶液。酮洛芬是最强的光敏剂(6/6),对舒洛芬(2/6)、噻洛芬酸(3/6)和二苯甲酮(6/6)表现出光交叉反应性。舒洛芬是一种强光敏剂(4/6),对酮洛芬(1/4)和噻洛芬酸(2/4)表现出光交叉反应性,但对二苯甲酮无反应。噻洛芬酸也是一种光敏剂(2/6),但仅对二苯甲酮(2/2)表现出光交叉反应性。二苯甲酮也是最强的光敏剂(6/6),但对上述三种化学物质无光交叉反应。

结论

从测试结果来看,苯甲酰基似乎是酮洛芬、舒洛芬和噻洛芬酸光敏性及光交叉反应性的关键结构。二苯甲酮的整个结构是诱导其光敏化所必需的。因二苯甲酮的整个结构而产生光敏化的动物对酮洛芬、舒洛芬或噻洛芬酸无光交叉反应。

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