Addition of UVA-absorber butyl methoxy dibenzoylmethane to topical ketoprofen formulation reduces ketoprofen-photoallergic reaction

Atarashi, Kenji; Takano, Masashi; Kato, Setsuko; Kuma, Hidekazu; Nakanishi, Masaru; Tokura, Y.

doi:10.1016/j.jphotobiol.2012.05.002

Cited by 15 publications

(8 citation statements)

References 27 publications

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“…This therapeutic activity against melanoma cells is particularly interesting for antimelanoma studies, because dibenzoylmethane derivatives can protect against UVA/UVB radiation, which plays a significant role in sunlight-induced skin damage. 15,26 Compounds 1-2 and 5-7 were not tested for antiproliferative activity due to the small amount of each sample available.…”

Section: Resultsmentioning

confidence: 99%

“…They prevent radiation from penetrating to vital cell components, and block overproduction of oxygen-derived free radicals, reducing skin damage from UV radiation in sunlight. 14,15 Significant antitumor, antimalarial and trypanocidal activities have recently been reported for a number of dibenzoylmethanes and synthetic derivatives. 16 We report here the isolation and characterization of three new dibenzoylmethane derivatives (1)(2)(3) together with four known compounds (4-7), from the root bark of M. filipes.…”

Section: Introductionmentioning

confidence: 99%

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Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo

Santos¹,

Jo²,

Marques³

et al. 2016

J. Braz. Chem. Soc.

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isolated from a dichloromethane extract from the root bark of Muellera filipes (Benth.) M.J. Silva & A.M.G. Azevedo, along with two dibenzoylmethane derivatives, 2'-methoxy-8-(α,α-dimethylallyl)-furano-(4'',5'':3',4')-dibenzoylmethane and 2'-hydroxy-8-(α,α-dimethylallyl)-2",2"-dimethylpyrano-(5",6":3',4')-dibenzoylmethane; one flavanone, isolonchocarpin and one flavone, pongaglabrone, which had been previously isolated from other sources. The molecular structures of the new dibenzoylmethane derivatives were determined by analysis of their spectral data (1 H and 13 C nuclear magnetic resonance (NMR), 2D-NMR, NOE (nuclear Overhauser effect) and HRMS (high resolution mass spectrometry). The known compounds were identified using 1D experiments and comparison with spectral data from the literature. 2'-O-(3'',3''-Dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4'',5'':3'4')-dibenzoylmethane displayed strong activity against the human cancer cell line OVCAR-3 (ovarian), and 2'-methoxy-8-(α,α-dimethylallyl)-furano-(4'',5'':3',4')-dibenzoylmethane showed high selectivity for cell lines NCI-H460 (lung) and UACC-62 (melanoma).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo

Santos¹,

Jo²,

Marques³

et al. 2016

J. Braz. Chem. Soc.

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“…To realize light-stable formulations, the use of light-absorbing agents represents one of the most widely investigated applications. The photoprotective effect of different ultraviolet (UV) filters has been evaluated with promising results in topical formulations of Ketoprofen, by adding butyl methoxy dibenzoylmethane [ 19 ]. The photostability of Diclofenac has been greatly increased by adding light absorbers such as octisilate, octyl methoxycinnamate and a combination of them to the gel formulations [ 7 ].…”

Section: Lipid Nanocarriers For Photoprotection Of Nsaidsmentioning

confidence: 99%

“…The first approach in light protection consists of the use of suitable packaging materials that shield visible and/or UV sun radiation. Otherwise, the addition of light-absorbent excipients in the formulation is often proposed to provide the photoprotection of the drugs [ 7 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Photodegradation of Anti-Inflammatory Drugs: Stability Tests and Lipid Nanocarriers for Their Photoprotection

et al. 2021

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The present paper provides an updated overview of the methodologies applied in photodegradation studies of non-steroidal anti-inflammatory drugs. Photostability tests, performed according to international standards, have clearly demonstrated the photolability of many drugs belonging to this class, observed during the preparation of commercial forms, administration or when dispersed in the environment. The photodegradation profile of these drugs is usually monitored by spectrophotometric or chromatographic techniques and in many studies the analytical data are processed by chemometric procedures. The application of multivariate analysis in the resolution of often-complex data sets makes it possible to estimate the pure spectra of the species involved in the degradation process and their concentration profiles. Given the wide use of these drugs, several pharmaceutical formulations have been investigated to improve their photostability in solution or gel, as well as the pharmacokinetic profile. The use of lipid nanocarriers as liposomes, niosomes or solid lipid nanoparticles has demonstrated to both minimize photodegradation and improve the controlled release of the entrapped drugs.

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“…Atarashi et al revealed that the addition of butyl methoxydibenzoylmethane into a topical formulation containing ketoprofen reduced the photoallergic reaction caused by this drug. Butyl methoxydibenzoylmethane is a UVA filter, but unlike octocrylene and benzophenone-3 shows no cross-reactivity with ketoprofen [111]. It should be emphasized that the benzophenone moiety in ketoprofen plays a key role in its photosensitivity reactions.…”

Section: Non-steroidal Anti-inflammatory Drugs (Nsaids)mentioning

confidence: 99%

Photostability of Topical Agents Applied to the Skin: A Review

2019

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Topical treatment modalities have multiple advantages starting with the convenient application and non-invasive treatment and ending with the reduction of the risk of the systemic side effects. Active pharmaceutical substances must reach the desired concentration at the target site in order to produce a particular therapeutic effect. In contrast to other dosage forms topical agents applied to the skin may also be susceptible to photodegradation after application. That is why the knowledge of the susceptibility of these topical drugs to UV irradiation, which may contribute to their degradation or changes in chemical structure, is very important. Active pharmaceutical substances used in dermatology may differ both in chemical structure and photostability. Furthermore, various factors-such as light intensity and wavelength, pH, temperature, concentration-can influence the photodegradation process, which is reflected in particular in kinetics of photodegradation of active pharmaceutical substances as well as both the quantitative and qualitative composition of by-products. The aim of this study was to conduct a systematic review of the photostability of dermatological drugs, as well as of other substances commonly applied topically. The photostability of glucocorticosteroids, retinoids, and antifungal drugs as well as non-steroidal anti-inflammatory drugs applied topically and selected UV-filters have been discussed. Furthermore, the impact of photoinstability on the effectiveness of pharmacotherapy and some photostabilization strategies have been also included. the active pharmaceutical ingredient (API) must reach the desired concentration at the target site so that it provides a particular therapeutic effect. Appropriate API concentration will be obtained after the application of the recommended amount of drug product (a finished dosage form) to the skin [4]. The skin is the largest organ of the human body (1.5-2.0 m 2 ) that protects against external environmental factors, and thus is exposed to, among others, UV radiation and xenobiotics. Overcoming the barrier that constitutes the skin is possible for lipophilic substances with log P in the range of 1-3 and those with a low molecular weight (MW < 500 Da) [2]. Therefore, many substances applied topically that penetrate through the stratum corneum, reach the dermis and via dermal microcirculation could get into the systemic circulation causing systemic effects [2,3,5].The stability studies of APIs and drug products are a priority in the research and development of drugs. Information about the stability of the drug is necessary to ensure its appropriate quality, effectiveness, and safety for the patients [6,7]. General rules for conducting stability tests are included in the Guidance for Industry Q1A(R2) Stability Testing of New Drug Substances and Products which was developed by International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use [8]. The ultimate goal of the stability studies is to provide industry...

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Addition of UVA-absorber butyl methoxy dibenzoylmethane to topical ketoprofen formulation reduces ketoprofen-photoallergic reaction

Cited by 15 publications

References 27 publications

Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo

Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo

Photodegradation of Anti-Inflammatory Drugs: Stability Tests and Lipid Nanocarriers for Their Photoprotection

Photostability of Topical Agents Applied to the Skin: A Review

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