Photochemically stabilized formulation of dacarbazine with reduced production of algogenic photodegradants

Uchida, Atsushi; Ohtake, Hiroto; Suzuki, Yukiko; Sato, Hideyuki; Seto, Yoshiki; Onoue, Satomi; Oguchi, Tamio

doi:10.1016/j.ijpharm.2019.04.063

Cited by 7 publications

(6 citation statements)

References 35 publications

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“…It was speculated that cysteine might protect photosensitive pharmaceuticals from photodegradation, due to its antioxidative activity. Other report showed that, in the case of dacarbazine, cysteine suppressed the generation of its photoproduct via its potential as a superoxide scavenger, but the residual rate of dacarbazine after photo-irradiation with cysteine was the same as that without it [ 16 ]. Tyrosine and tryptophan had no antioxidative potencies in the PAO test, indicating that they showed protective effects on NX photodegradation by other natures.…”

Section: Resultsmentioning

confidence: 99%

Photoprotective Effects of Selected Amino Acids on Naproxen Photodegradation in Aqueous Media

et al. 2020

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It is important to develop a photostabilization strategy to ensure the quality of photosensitive compounds, including pharmaceuticals. This study focused on the protective effects of 20 amino acids on the photodegradation of naproxen (NX), a photosensitive pharmaceutical, to clarify the important nature of a good photostabilizer. Our previous report indicated the photodegradability of NX and the protective effects of some antioxidants on its photodegradation, therefore, this compound was used as a model compound. The degradation of NX in aqueous media during ultraviolet light (UV) irradiation and the protective effects of selected amino acids were monitored through high-performance liquid chromatography (HPLC), equipped with a reverse-phase column. Addition of cysteine, tryptophan, and tyrosine induced the significant suppression of NX photodegradation after UV irradiation for 3 h (residual amount of NX; 15.35%, 6.82%, and 15.64%, respectively). Evaluation of the antioxidative activity and UV absorption spectrum showed that cysteine suppressed NX degradation through its antioxidative ability, while tryptophan and tyrosine suppressed it through their UV filtering ability. Furthermore, three amino acids at higher concentrations (more than 100 µmol/L) showed more protective effects on NX photodegradation. For 10 mmol/L, residual amounts of NX with cysteine, tryptophan, and tyrosine were 58.51%, 69.34%, and 82.40%, respectively. These results showed the importance of both photoprotective potencies (antioxidative potency and UV filtering potency) and stability to UV irradiation for a good photostabilizer of photosensitive pharmaceuticals.

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Section: Resultsmentioning

confidence: 99%

Photoprotective Effects of Selected Amino Acids on Naproxen Photodegradation in Aqueous Media

et al. 2020

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“…Both drugs are known to undergo fast photodegradations. Their kinetics have usually been fitted to 0th- or 1st-order models, irrespective of whether the light employed was mono- or polychromatic 1 – 3 , 9 , 43 – 48 . In aqueous solutions, their photodegradations produce species responsible of phototoxic effects 1 – 3 , 9 , 46 .…”

Section: Introductionmentioning

confidence: 99%

Photokinetics of Dacarbazine and Nifedipine under polychromatic light irradiation and their application as new reliable actinometers for the ultraviolet range

Maafi

Al-Qarni

2022

Sci Rep

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The photokinetic behaviour of drugs driven by polychromatic light is an area of pharmaceutics that has not received a lot of attention. Most often, such photokinetic data is treated by thermal kinetic models (i.e., the classical 0th-, 1st- or 2nd-order equations). Such models were not analytically derived from the rate-laws of the photodegradation reactions. Polychromatic light kinetic modelling is hence of importance, as a means to providing adequate toolkits and metrics. This paper aims at proposing two reliable drug-actinometers useful for polychromatic UVA range. The general actinometric methodology offered here is also useful for any drugs/materials obeying a primary photoprocess where both reactant and photoproduct absorb the incident light, of the $$AB{(1\Phi )}_{{\varepsilon }_{B}\ne 0}$$ A B ( 1 Φ ) ε B ≠ 0 type. The present method has been consolidated by the η-order kinetics. This framework further demonstrated the lamp-specificity of actinometers. Overall, Dacarbazine and Nifedipine photodegradations obeyed η-order kinetics, and stand as effective actinometers that can be recommended for the ICH Q1b photostability testing.

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“…DTIC is an anticancer drug indicated for the treatment of metastatic malignant melanoma and soft tissue sarcoma, being also used in the treatment of early Hodgkin lymphoma. , Although it may be ionized, this API is commercialized in a neutral form as an intravenous formulation, exhibiting pH-dependent aqueous solubility and a pronounced photodegradation when exposed to light. , The main photodegradation product, 2-azahypoxanthine (2-AZA), is pharmacologically inactive and further responsible for some adverse reactions. , To reduce photodegradation, freshly prepared DTIC solutions protected from light must be intravenously administered as quickly as possible. , Recently, Uchida et al developed a photochemically stabilized formulation of DTIC using reactive oxygen species. The lack of scientific reports on this line reinforces the idea that the emergence of alternative and safe technologies to overcome DTIC issues remains highly demanded.…”

Section: Introductionmentioning

confidence: 99%

“… 20 , 21 To reduce photodegradation, freshly prepared DTIC solutions protected from light must be intravenously administered as quickly as possible. 22 , 23 Recently, Uchida et al 24 developed a photochemically stabilized formulation of DTIC using reactive oxygen species. The lack of scientific reports on this line reinforces the idea that the emergence of alternative and safe technologies to overcome DTIC issues remains highly demanded.…”

Section: Introductionmentioning

confidence: 99%

Highly Soluble Dacarbazine Multicomponent Crystals Less Prone to Photodegradation

Diniz,

Carvalho,

Souza

et al. 2024

Mol. Pharmaceutics

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Photochemically stabilized formulation of dacarbazine with reduced production of algogenic photodegradants

Cited by 7 publications

References 35 publications

Photoprotective Effects of Selected Amino Acids on Naproxen Photodegradation in Aqueous Media

Photoprotective Effects of Selected Amino Acids on Naproxen Photodegradation in Aqueous Media

Photokinetics of Dacarbazine and Nifedipine under polychromatic light irradiation and their application as new reliable actinometers for the ultraviolet range

Highly Soluble Dacarbazine Multicomponent Crystals Less Prone to Photodegradation

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