When can cyclodextrins be considered for solubilization purposes?

Rao, Venkatramana M.; Stella, Valentino J.

doi:10.1002/jps.10341

Cited by 92 publications

(50 citation statements)

References 16 publications

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“…This tradeoff between solubility increase and permeability decrease can lead to paradoxical effects on the overall absorption. For example, a critical review of the literature reveals that the use of cyclodextrins may lead to improved, unchanged, or even reduced fraction of drug absorbed (23,24). Further reports have emerged in the literature which has made apparent these opposing effects of cyclodextrins on the solubility and the permeability, and qualitative guidelines have been suggested for the proper use of cyclodextrins (20,24,25).…”

Section: S-p Interplay From Cyclodextrin-based Systemsmentioning

confidence: 99%

“…For example, a critical review of the literature reveals that the use of cyclodextrins may lead to improved, unchanged, or even reduced fraction of drug absorbed (23,24). Further reports have emerged in the literature which has made apparent these opposing effects of cyclodextrins on the solubility and the permeability, and qualitative guidelines have been suggested for the proper use of cyclodextrins (20,24,25). More recently, quantitative analyses have emerged that enable simulation of the solubility-permeability interplay and the overall effect of cyclodextrins on intestinal membrane permeability (26)(27)(28)(29).…”

Section: S-p Interplay From Cyclodextrin-based Systemsmentioning

confidence: 99%

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The Solubility–Permeability Interplay and Its Implications in Formulation Design and Development for Poorly Soluble Drugs

Dahan

Miller

2012

AAPS J

241

130

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Abstract. While each of the two key parameters of oral drug absorption, the solubility and the permeability, has been comprehensively studied separately, the relationship and interplay between the two have been largely ignored. For instance, when formulating a low-solubility drug using various solubilization techniques: what are we doing to the apparent permeability when we increase the solubility? Permeability is equal to the drug's diffusion coefficient through the membrane times the membrane/aqueous partition coefficient divided by the membrane thickness. The direct correlation between the intestinal permeability and the membrane/aqueous partitioning, which in turn is dependent on the drug's apparent solubility in the GI milieu, suggests that the solubility and the permeability are closely associated, exhibiting a certain interplay between them, and the current view of treating the one irrespectively of the other may not be sufficient. In this paper, we describe the research that has been done thus far, and present new data, to shed light on this solubility-permeability interplay. It has been shown that decreased apparent permeability accompanies the solubility increase when using different solubilization methods. Overall, the weight of the evidence indicates that the solubility-permeability interplay cannot be ignored when using solubility-enabling formulations; looking solely at the solubility enhancement that the formulation enables may be misleading with regards to predicting the resulting absorption, and hence, the solubility-permeability interplay must be taken into account to strike the optimal solubility-permeability balance, in order to maximize the overall absorption.

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Section: S-p Interplay From Cyclodextrin-based Systemsmentioning

confidence: 99%

Section: S-p Interplay From Cyclodextrin-based Systemsmentioning

confidence: 99%

The Solubility–Permeability Interplay and Its Implications in Formulation Design and Development for Poorly Soluble Drugs

Dahan

Miller

2012

AAPS J

241

130

View full text Add to dashboard Cite

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“…Various studies reported in the literature related to cyclodextrin complexes showed that the permeability of drugs was increased or decreased through biological barriers. [87][88][89][90][91] Cyclodextrins increase the drug solubility at the absorption site which may enhance the permeability without changes in the physicochemical properties of the drugs. Some observations indicated that drug permeability of drugs can be enhanced through the barriers using penetration enhancers.…”

Section: Permeability Enhancementmentioning

confidence: 99%

Untitled

Budhwar¹

2018

AJP

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Inclusion complexes have various applications in different fields of drug delivery and pharmaceutical industry due to their ability of complexation with guest molecules and enhancement of the physicochemical properties of guest molecules. Cyclodextrins and their derivatives have the ability to encapsulate the bioactive compounds into its cavity and protect these from the environmental conditions, improve the solubility, bioavailability, and other properties also. The aim of this review is to highlight the advantages of cyclodextrins in the enhancement of physicochemical properties of drugs (such as solubility, stability, bioavailability, permeability, and others), different methods for production and various characterization techniques used for evaluation of complexes. Applications of cyclodextrin complexes in pharmaceutical and other fields are also explained here with examples. Thus cyclodextrins, because of their continuing ability to find several novel applications in drug delivery, are expected to solve many problems accompanied with the delivery of different novel drugs through various delivery routes.

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“…H3 and H5 protons of glucose (or modified glucose) units of cyclodextrins are facing the interior of the CD cavity whereas H6 protons are located in its rim. All the other protons (H1 , H2 , and H4 ) are located outside the cavity [27,28]. The guesthost inclusion process will produce variable changes in the chemical shifts ( ) of some hydrogens belonging either to the ligand or the CD.…”

Section: Fourier Transform Infrared Spectroscopy (Ftir)mentioning

confidence: 99%

Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modifiedβ-Cyclodextrin

Garrido

Rodrigues

Milhazes

et al. 2017

Journal of Chemistry

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The herbicide terbuthylazine (TBA) is widely used for preemergence or postemergence control of many grass and broadleaf weeds and has, besides other issues, a poor aqueous solubility profile that results in reduced bioavailability. Cyclodextrins and modified cyclodextrins were considered, among other substances, appropriate agents for improving pesticide water solubility. Therefore, the inclusion complex formation of terbuthylazine with -cyclodextrin ( -CD) and hydroxypropyl--cyclodextrin (HP--CD) was studied to attain its aqueous solubility enhancement. Their characterization was accomplished with different analytical techniques, namely, by UV-Vis, DSC, FTIR, and 1 H NMR. From the analysis of the complexation performance of the herbicide it was concluded that the interaction of terbuthylazine with CDs leads to the formation of inclusion complexes with a stoichiometry of 1 : 1. The association constants of the TBA/ -CD and TBA/HP--CD complexes were determined by UV. The mean values obtained for the stability constants are 460.4 ± 26.5 and 532.1 ± 27.6 to TBA/ -CD and TBA/HP--CD, respectively.1 H NMR data corroborate the formation of the TBA/ -CD and TBA/HP--CD complexes synthesized by the kneading method. A formulation incorporating TBA cyclodextrin complexes might lead to an improvement in terbuthylazine bioavailability. The development of TBA-CD formulations may be interesting since it would enable, through their inclusion into the hydrophobic cavity of CDs, enhancement of solubility, bioavailability, and stability of the herbicide.

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When can cyclodextrins be considered for solubilization purposes?

Cited by 92 publications

References 16 publications

The Solubility–Permeability Interplay and Its Implications in Formulation Design and Development for Poorly Soluble Drugs

The Solubility–Permeability Interplay and Its Implications in Formulation Design and Development for Poorly Soluble Drugs

Untitled

Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modifiedβ-Cyclodextrin

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