The utility of cyclodextrins for enhancing oral bioavailability

Miller, Lee A.; Ahmed, Imran

doi:10.1016/j.jconrel.2007.07.018

Cited by 472 publications

(250 citation statements)

References 102 publications

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“…Lower corneal permeability of Δ 8 -THC in the presence of SβCD can be attributed to the higher magnitude of the binding constant with SβCD (Table IV). A number of reports indicate that the magnitude of the binding constant plays an important role in oral bioavailability of drug-cyclodextrin complexes (40). A very high binding constant value can lead to the presence of decreased free drug fraction at the corneal surface, leading to reduced membrane permeability.…”

Section: Discussionmentioning

confidence: 99%

Enhanced Solubility, Stability, and Transcorneal Permeability of Delta-8-Tetrahydrocannabinol in the Presence of Cyclodextrins

et al. 2011

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Abstract. The purpose of this study was to investigate the effect of cyclodextrins (CDs) on aqueous solubility, stability, and in vitro corneal permeability of delta-8-tetrahydrocannabinol (Δ 8 -THC). Phase solubility of Δ 8 -THC was studied in the presence of 2-hydroxypropyl-β-cyclodextrin (HPβCD), randomly methylated-β-cyclodextrin (RMβCD) and sulfobutyl ether-β-cyclodextrin sodium salt (SβCD). Stability of Δ 8 -THC in 5% w/v aqueous CD solutions, as a function of pH, was studied following standard protocols. In vitro corneal permeation of Δ 8 -THC (with and without CDs) across excised rabbit cornea was also determined. Phase-solubility profile of Δ 8 -THC in the presence of both HPβCD and RMβCD was of the A P type, whereas, with SβCD an A L type was apparent. Aqueous solubility of Δ 8 -THC increased to 1.65, 2.4, and 0.64 mg/mL in the presence of 25% w/v HPβCD, RMβCD, and SβCD, respectively. Significant degradation of Δ 8 -THC was not observed within the study period at the pH values studied, except for at pH 1.2. Transcorneal permeation of Δ 8 -THC was dramatically improved in the presence of CDs. The results demonstrate that CDs significantly increase aqueous solubility, stability, and transcorneal permeation of Δ 8 -THC. Thus, topical ophthalmic formulations containing Δ 8 -THC and modified beta CDs may show markedly improved ocular bioavailability.

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Section: Discussionmentioning

confidence: 99%

Enhanced Solubility, Stability, and Transcorneal Permeability of Delta-8-Tetrahydrocannabinol in the Presence of Cyclodextrins

et al. 2011

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“…Cyclodextrins are useful excipients widely used in pharmaceutical formulations as complexing agents, especially for their ability to interact with poorly water soluble drugs (BCS Class II and IV) in order to increase their apparent water solubility and therefore their oral bioavailability (Arun, 2008;Brewster and Loftsson, 2007;Del Valle, 2004;Nitalikar et al, 2012). Cyclodextrins can also be used to modify drug stability, to reduce undesirable drug side effects such as gastrointestinal drug irritation, to mask undesirable taste and to control the drug release from modified-release devices (Carrier et al, 2007;Ono et al, 2011;Szejtli and Szente, 2005). Moreover, CDs can be used as active ingredients in the treatment of pathologies such as Niemann-Pick disease (Camargo et al, 2001) thanks to their abilities to interact with cholesterol.…”

Section: Introductionmentioning

confidence: 99%

Rapid quantification of 2-hydroxypropyl-β-cyclodextrin in liquid pharmaceutical formulations by 1H nuclear magnetic resonance spectroscopy

Dufour

Évrard

Tullio

2015

European Journal of Pharmaceutical Sciences

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a b s t r a c tQuantification of 2-hydroxypropyl-b-cyclodextrin (2-HP-b-CD) is not yet described in United States Pharmacopeia (USP) and European Pharmacopeia (EP). A useful quality control tool is therefore needed for the specific quantification in finished liquid pharmaceutical products, especially for formulations containing 2-HP-b-CD as an active ingredient. A new technique is also mandatory for the development of future formulations in which 2-HP-b-CD concentration could influence the properties of these formulations. Here, we described the use of 1 H NMR for the rapid quantification of 2-HP-b-CD directly into pharmaceutical solutions without any extraction or separation steps. This technique was successfully applied to different pharmaceutical solutions comprising an i.v. solution (budesonide/2-HP-b-CD complex), an eye drop solution (Indocollyre Ò ) and an oral solution (Sporanox Ò ). Specificity, linearity, precision (repeatability and intermediate precision), trueness, limits of quantification (LOQs) and accuracy were used as validation criteria.

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“…availability of insoluble drugs. [14][15][16][17] Their unique physicochemical property including a hydrophilic external surface and an internal hydrophobic cavity allows the formation of host-guest interactions with hydrophobic organic compounds. 18 The widely natural CDs are made up of 6-8 oligosaccharides units joined with each other through 1-4 bonds, they are called α-, β-, γ-CDs, respectively.…”

Section: Introductionmentioning

confidence: 99%

Inclusion Complex of Artemether with 2-Hydroxypropyl -β-Cyclodextrin for the Treatment of Malaria: Preparation, Characterization and Evaluation

Hao¹,

Chen²,

Tian³

et al. 2017

MOJBB

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Abbreviations: ATM, artemether; DSC, differential scanning calorimetry; FT-IR, fourier transform infrared spectroscopy; AUC, area under curve; MRT, mass rapid transit; CDs, cyclodextrins; HPLC, high performance liquid chromatography; LE, load efficiency IntroductionMalaria has a serious influence on human beings especially on that in tropical and subtropical countries. It is reported that there are approximately 300-500 million in clinical and 1.5-2.7 million in death every year. Among them, Plasmodium falciparum is the main protozoon for fatal cases. 1 With the widespread drug resistance limited by older therapies dominated by quinine, standard therapy for malaria is now artemisinin-based chemotherapy which is genuine and of high quality. 2 Artemether, [3R-(3R,5aS,6S,8aS,9R ,10R,12S,12aR)]- 6,-1,2-benzodioxepin, 3 is one of the lipidsoluble derivative of artemisinin, which has proved to be efficient against malaria especially for malignant malaria. 4 The structural formula is shown in Figure 1A. ATM disturbs the mitochondrial function, influence ultrastructure, and block the nutritional intake of Plasmodium falciparum, making them to lose cytoplasm and nutrients and cannot get replenish and soon died. 5,6 ATM belongs to BCS IV drug with poorly soluble and poorly permeable peculiarity. 7 ATM is only available as a pre-mixed oilbased solution for intramuscular injection. And there is evidence that the intramuscular injection may not be absorbed absolutely and can cause terrible pain to patient. 8,9 The novel delivery system such as liposome 10 and nanostructured lipid 11 of ATM did not achieve its aim of improving anti-malarial therapeutic efficiency. In addition, its poor bioavailability and rapid clearance from the body limits its exploitation and application in clinical study. From the analysis mentioned above, we can realize the importance of improving its solubility and bioavailability. Several formulation approach could be used to improving the solubility along with bio-availability of insoluble drugs. 12 Until now, different formulations are reported such as Solid Dispersion System, 7 nanoparticle, 13 inclusion complex. 1 Among them, inclusion complex is widely elected due to their mass production achieved easily.As a kind of functional excipients, cyclodextrins (CDs) have been used extensively in pharmaceutical formulations to improve the bio- AbstractArtemether (ATM) is being evaluated for use in Malaria at present. However, its poor solubility in water limits its exploitation and application in clinical. The purpose of this work is to develop inclusion complex of ATM with 2-hydroxypropyl-β-cyclodextrin (ATM-2-HP-β-CD inclusion complex) which have the ability to improve the solubility and oral bioavailability of ATM. The ATM-2-HP-β-CD inclusion complex was prepared by Solution mixing method at the mole ratio of 1:36 (ATM: HP-2-β-CD). The average drug entrapment efficiency and loading capacity were 97.66±1.22% and 2.64±0.03%, respectively. The formation of ATM-2-HP-β-CD inclusion complex was verified by ...

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The utility of cyclodextrins for enhancing oral bioavailability

Cited by 472 publications

References 102 publications

Enhanced Solubility, Stability, and Transcorneal Permeability of Delta-8-Tetrahydrocannabinol in the Presence of Cyclodextrins

Enhanced Solubility, Stability, and Transcorneal Permeability of Delta-8-Tetrahydrocannabinol in the Presence of Cyclodextrins

Rapid quantification of 2-hydroxypropyl-β-cyclodextrin in liquid pharmaceutical formulations by 1H nuclear magnetic resonance spectroscopy

Inclusion Complex of Artemether with 2-Hydroxypropyl -β-Cyclodextrin for the Treatment of Malaria: Preparation, Characterization and Evaluation

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