Effect of γ-cyclodextrin on solubilization and complexation of irbesartan: Influence of pH and excipients

Muankaew, Chutimon; Jansook, Phatsawee; Stefánsson, Einar; Loftsson, Þorsteinn

doi:10.1016/j.ijpharm.2014.08.013

Cited by 32 publications

(15 citation statements)

References 57 publications

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“…However, the values obtained for the same complex may vary depending on the environmental condition. For example, the presence of water‐soluble polymers in the aqueous complexation media might increase the value of K 1:1 and addition of chaotropic agents (e.g. urea) might decrease K 1:1 .…”

Section: Inclusion Complex Formation and Self‐aggregatesmentioning

confidence: 99%

Cyclodextrin‐Based Formulations: A Non‐Invasive Platform for Targeted Drug Delivery

Muankaew

Loftsson

2017

Basic Clin Pharma Tox

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157

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Cyclodextrins (CDs) are recognized as promising pharmaceutical excipients due to their unique ability to form watersoluble inclusion complexes with various poorly soluble compounds. The numerous investigations on CDs and their use in nanomedicine have received considerable attention in the last three decades, leading to the rapid development of new CD-containing formulations that significantly facilitate targeted drug delivery and controlled drug release, with consequent improvements in drug bioavailability. This MiniReview highlights the efficacy and recent uses of CDs for non-invasive drug delivery. Using ophthalmic and nasal drug delivery as examples, an overview of chemical properties, mechanisms of CDs on drug solubilization, stabilization and permeation, along with their toxicological profiles relevant to nasal and ocular administration, are provided and discussed. The recent development and application of CD-based nanocarrier systems for targeted drug delivery are summarized.Cyclodextrins (CDs) are natural cyclic oligosaccharides that are produced by enzymatic degradation of starch. There are three native CDs designated aCD, bCD and cCD, which are composed of 6, 7 and 8 D-glucopyranose units linked by a-(1, 4) glycosidic, respectively [1]. The molecules are commonly described as truncated cone, bucket-like or donut-shaped, with a hydrophilic outer surface and a relatively hydrophobic inner cavity that allows entrapment of small hydrophobic drug molecules or hydrophobic moieties of larger molecules [2], thereby providing drugs with new physicochemical characteristics without altering their intrinsic properties. Table 1 summarizes the characteristics of different CDs. Natural CDs are preferred for complexation; however, their usability is limited by the small cavity size of aCD, poor aqueous solubility of bCD and low productivity of cCD [3]. Derivatized CDs can be obtained by substituting their hydroxyl groups with desired functional moieties. Methyl-(MebCD and MecCD) [4,5], hydroxypropyl-(HPaCD, HPbCD and HPcCD) [6][7][8] and sulphobutylether (SEBbCD) derivatives [9] are frequently found in pharmaceutical products and have improved solubility and inclusion capacity over natural CDs. Pharmaceutical applications of both natural CDs and their derivatives are common when drug/CD complexes are used to increase drug solubility, improve organoleptic properties [10], enhance drug permeation [11] and increase drug stability, resulting in increased product shelf-life and drug bioavailability [12]. In addition, spontaneous self-assembly of drug/CD complexes into aggregates can lead to innovative drug delivery systems, such as CD-containing liposomes and microspheres as well as microand nanoparticles [13]. Polymerized CDs (e.g. Epi-aCD and Epi-bCD) have also been synthesized to enhance the selfassembly ability of CDs, and to strengthen their interactions with drugs and biological membranes [14]. Compared with other pharmaceutical excipients, CDs have been shown to reduce the toxicity of several drugs and are...

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Section: Inclusion Complex Formation and Self‐aggregatesmentioning

confidence: 99%

Cyclodextrin‐Based Formulations: A Non‐Invasive Platform for Targeted Drug Delivery

Muankaew

Loftsson

2017

Basic Clin Pharma Tox

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157

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“…There have been numerous reports of the use of CD as a release modifier for selected molecules [ 14 – 16 ]. The release profiles for CTZ and the CTZ–β-CD system are presented in Fig.…”

Section: Resultsmentioning

confidence: 99%

Effects of inclusion of cetirizine hydrochloride in β-cyclodextrin

Paczkowska

Mizera

Lewandowska

et al. 2018

J Incl Phenom Macrocycl Chem

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Following the preparation of inclusion complex of cetirizine (CTZ) and β-cyclodextrin (β-CD), the compound was investigated to assess the possibility of modifying the physicochemical properties (solubility, release, stability, permeability) of CTZ after complexation that are vital for subsequent formulation studies involving the said complex. Changes in FT-IR/Raman spectra, DSC thermograms and XRD diffractograms confirmed the formation of a CTZ–β-CD system. Hydrophilic interaction chromatography with a DAD detector was employed to determine alterations of the CTZ concentration during studies following complexation. An analysis of a phase-solubility diagram of cCTZ = fcβ-CD indicated a linear rise in the solubility of CTZ as the concentration of β-CD increased. The inclusion of CTZ in a system with β-CD significantly reduced the instability of CTZ in the presence of oxidizing factors. It was also found that regardless of the pH of the acceptor fluids used in the release studies an increase was observed in the concentration of CTZ in CD system compared to its free form. The ability to permeate artificial biological membranes manifested by CTZ after complexation was enhanced as well. In summary, CD has significant potential to mask the bitter taste of CTZ and to counter the instability induced by oxidizing factors.

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“…In the formulation development process, methylcellulose, a carbohydrate polymer, was used to prevent aggregation of the nanoparticles. Methylcellulose gel is a frequently used pharmaceutical excipient, [30][31][32] which can form interpenetrating polymer network microspheres providing slow release of various drugs. 31 While the particle size increased to 250 nm, it remained in the acceptable range for intracellular penetration and maintained its stability in the presence of cell culture medium.…”

Section: Discussionmentioning

confidence: 99%

Evaluation of β-cyclodextrin-modified gemini surfactant-based delivery systems in melanoma models

Michel

Mohammed-Saeid

Getson

et al. 2016

IJN

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Effect of γ-cyclodextrin on solubilization and complexation of irbesartan: Influence of pH and excipients

Cited by 32 publications

References 57 publications

Cyclodextrin‐Based Formulations: A Non‐Invasive Platform for Targeted Drug Delivery

Cyclodextrin‐Based Formulations: A Non‐Invasive Platform for Targeted Drug Delivery

Effects of inclusion of cetirizine hydrochloride in β-cyclodextrin

Evaluation of β-cyclodextrin-modified gemini surfactant-based delivery systems in melanoma models

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Effect of γ-cyclodextrin on solubilization and complexation of irbesartan: Influence of pH and excipients

Cited by 32 publications

References 57 publications

Cyclodextrin‐Based Formulations: A Non‐Invasive Platform for Targeted Drug Delivery

Cyclodextrin‐Based Formulations: A Non‐Invasive Platform for Targeted Drug Delivery

Effects of inclusion of cetirizine hydrochloride in β-cyclodextrin

Evaluation of &beta;-cyclodextrin-modified gemini surfactant-based delivery systems in melanoma models

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Evaluation of β-cyclodextrin-modified gemini surfactant-based delivery systems in melanoma models