Photostability of piroxicam in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

Nikolić, D.; Ilić‐Stojanović, Snežana; Nikolic, B Ljubisa; Cakic, D Milorad; Zdravkovic, Steven A.; Kapor, J Agnes; Popsavin, Mirjana

doi:10.2298/hemind130306034n

Cited by 16 publications

(28 citation statements)

References 21 publications

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“…Aromatic ketones moved the molar absorptivity towards higher wavelengths and consequently acted as more photosensitive agents [23]. A recent research showed the improved photostability of the usnic acid and piroxicam in the inclusion complexes with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) [24,25].…”

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confidence: 99%

The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

Ilić‐Stojanović¹,

Nikolić²,

Nikolić³

et al. 2015

Hem Ind

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The aim of this work was the preparation of the inclusion complex of naproxen with 2hydroxypropyl-β-cyclodextrin (HP-β-CD) in order to improve the physical and chemical properties of naproxen. The molecular inclusion complexes of naproxen with HP-β-CD were prepared by using the co-precipitation method in the solid state with the molar ratio of 1:1. The structure of the obtained complex was characterized by using FTIR, 1 H NMR, UV-Vis and XRD methods. The testing of naproxen photostability by the UV-Vis method indicated the degradation to aromatic ketone, 2-acetyl-6-methoxynaphthalene. FTIR analysis showed that the degradation has started 15 days after the exposure of naproxen to daylight while the inclusion complex of naproxen:2-hydroxypropyl-β-cyclodextrin was photostable for a period of 30 days.

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confidence: 99%

The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

Ilić‐Stojanović¹,

Nikolić²,

Nikolić³

et al. 2015

Hem Ind

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“…The X-ray diffractometry studies (Figure 3) confirm the crystalline nature of PX and β-CD, as well as the amorphous state of Me-β-CD and HP-β-CD. PX have a number of sharp peaks at 9.1°, 10.3°, 15.2°, 15.9°, 16.4°, 17.2°, 19.8°, 23.1°, 26.4°, and 27.1° [26]. Some of these peaks are already present in the diffractograms of physical mixtures, but appear of lower intensity compared to those of the pure drug.…”

Section: Resultsmentioning

confidence: 99%

“…PX exhibits characteristic bands at 3330 cm −1 (-NH stretching), 2970 cm −1 (-OH stretching), and 1630 cm −1 (C=O group of the cubic form) [15]. The spectra of CDs present a profile without distinctly high peaks in the range of 3000–3700 cm −1 (–OH groups) and in the range of 2800–3000 cm −1 (C-H groups) [14,26,27]. Physical mixtures shows the presence of both components (PX and CD).…”

Section: Resultsmentioning

confidence: 99%

In Vitro and Ex Vivo Evaluation of Tablets Containing Piroxicam-Cyclodextrin Complexes for Buccal Delivery

et al. 2019

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In the current study, the development of mucoadhesive tablets for buccal delivery of a non-steroidal anti-inflammatory drug was investigated. Binary complexes with piroxicam and cyclodextrins (β-cyclodextrin (β-CD), methylated-β-cyclodextrin (Me-β-CD), and hydroxypropyl-β-cyclodextrin (HP-β-CD)) were prepared by the co-evaporation method. All formulations were characterized by means of differential scanning calorimetry, infrared spectroscopy and powder X-ray diffractometry. Mucoadhesive tablets of binary systems were formulated by direct compression using chitosan as mucoadhesive polymer. The in vitro release profiles of tablets were conducted in simulated saliva and, the drug permeation studies, across porcine buccal mucosa. The results suggest that the rank order effect of cyclodextrins for the drug release was Me-β-CD > HP-β-CD > β-CD, whereas the ex vivo studies showed that the tablets containing chitosan significantly increased the transport of the drug compared to their free complexes. Finally, histological assessment revealed loss of the superficial cell layers, which might be attributed to the presence of cyclodextrins.

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“…Glucocorticosteroids pregna-1,4-dien-3,20-diones [24] betamethasone and its esters [25,26] betamethasone-17 valerate [27] mometasone furoate [28] hydrocortisone 21-acetate [29] prednisolone [30] fluocinolone 16,17-acetonide [31,32] desonide [33,34] Retinoids vitamin A [35] tretinoin [36][37][38][39][40][41][42][43][44] isotretinoin [36,37,45] adapalene [46,47] tazarotene [48] Antifungal drugs clotrimazole [49,50] bifonazole [51] itraconazole [52,53] terbinafine [54] Non-steroidal antiinflammatory drugs piroxicam [55][56][57] naproxen [58][59][60][61] diclofenac [57,58,62] ketoprofen [63][64][65][66] ibuprofen …”

Section: Drug Class Active Pharmaceutical Ingredientmentioning

confidence: 99%

“…The relationship between pH and the degradation rate is U-shaped, with an increase in the degradation rate in acidic and alkaline regions [109]. The inclusion complex of piroxicam with 2-hydroxypropyl-β-cyclodextrin increases the photostability by offering protection from daylight for up to 30 days [56]. Glass et al identified four photodegradation products of piroxicam after irradiation of its methanolic solution: (i) 2-methyl-1,2-benzisothiazol-3(2H)-one1,1-dioxide; (ii) N-(2-pyridyl)-methoxy-formyl-amide as a result of oxygen incorporation into piroxicam; (iii) N-(2-pyridyl)-methoxyamide being a result of decarbonylation of N-(2-pyridyl)-methoxy-formyl-amide; and (iv) N-methyl-N -(2-pyridyl)-ethane-diamide formed as a consequence of cleavage of the sulfur-nitrogen bond in the carboxylic acid.…”

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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Photostability of piroxicam in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

Cited by 16 publications

References 21 publications

The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

In Vitro and Ex Vivo Evaluation of Tablets Containing Piroxicam-Cyclodextrin Complexes for Buccal Delivery

Photostability of Topical Agents Applied to the Skin: A Review

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