Pharmaceutical Uses of Cyclodextrins and Derivatives

Duchêne, Dominique; Wouessidjewe, Denis

doi:10.3109/03639049009058543

Cited by 139 publications

(64 citation statements)

References 34 publications

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“…CDs are able to form inclusion complexes with poorly water-soluble drugs. These inclusion complexes have been shown to improve the stability, solubility, dissolution rate, and bioavailability of the drugs [2]. The hydroxypropyl-β-cyclodextrin (HPβCD) is highly watersoluble due to both its chemical nature and amorphous property, and does not have limitations such as the renal toxicity associated with β-cyclodextrins (βCD) or other chemically modified cyclodextrins [3,4].…”

Section: Introductionmentioning

confidence: 99%

Improved Pharmacokinetics of Aceclofenac Immediate Release Tablets Incorporating ist Inclusion Complex with Hydroxypropyl-β-Cyclodextrin

Dahiya

Kaushik²,

Pathak

2015

Sci. Pharm.

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The present investigation reports the various pharmacokinetic parameters of immediate release aceclofenac tablets incorporating its inclusion complex with hydroxypropyl-β-cyclodextrin. The tablets were prepared using aceclofenac: hydroxypropyl-β-cyclodextrin in a 1:1 molar ratio by the direct compression method (TKN). The results were compared with those of the marketed brand (MKT) and pure drug (TAC). The P-values indicated that mean plasma concentrations were significantly different among all three formulations administered (P<0.05, P<0.01). TKN showed significantly higher plasma levels when compared to the pure drug (P<0.01). The C max and AUC (0-∞) of TKN were significantly higher (P<0.05) compared to the pure drug and marketed formulation. Furthermore, the first-order overall elimination rate constant (K el ) of TKN was also significantly higher (P<0.05) compared to the pure drug and its marketed formulation. These results suggested that tablets prepared by incorporating the AC-HPβCD inclusion complex (TKN) would provide a more rapid onset of pharmacological effects in comparison to the marketed formulation and pure drug.

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Section: Introductionmentioning

confidence: 99%

Improved Pharmacokinetics of Aceclofenac Immediate Release Tablets Incorporating ist Inclusion Complex with Hydroxypropyl-β-Cyclodextrin

Dahiya

Kaushik²,

Pathak

2015

Sci. Pharm.

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“…These inclusion complexes have been shown to improve the stability, solubility, dissolution rate, and bioavailability of the drug. 5,6 The improvement in hydrophilicity is obtained through the formation of inclusion complexes where the host/guest interaction is dependent on the dimension of the oligosaccharide ring, and/or by means of highly homogeneous assembly between the CD and the drug in the solid state. In most cases these associations provide amenable solution behavior of poorly soluble drugs.…”

Section: Introductionmentioning

confidence: 99%

Physicochemical characterization and dissolution properties of nimesulide-cyclodextrin binary systems

et al. 2003

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side effects, and a high therapeutic index.1 N is a relatively weak inhibitor of prostaglandin synthesis in vitro and appears to exert its effect through a variety of mechanisms including free radical scavenging, effects on histamine release, the neutrophil myeloperoxidase pathway, bradykinin activity, tumor necrosis factor-a release, cartilage degradation, metalloprotease synthesis, phosphodiesterase type IV inhibition, platelet aggregation, and synthesis of platelet activating factor. It also exhibits a significant selectivity toward cyclooxygenase-2 (COX-2) versus COX-1 inhibition, which may explain the lower incidence of gastric side effects. However, recent findings reported that N has a higher risk of hepatic toxicity when compared to other marketed NSAIDs.2,3 Like many nonsteroidal anti-inflammatory drugs, N is very sparingly soluble in water (≈ 0.01 mg/mL). 4 The poor aqueous solubility and wettability of N gives rise to difficulties in pharmaceutical formulations for oral or parenteral delivery, which may lead to variable bioavailability. To overcome these drawbacks, increasing the aqueous solubility of N is an important goal. Hence, in this investigation, inclusion complexation of N was tried with α-, β-, and γ-cyclodextrins (CDs) with the aim to improve its pharmaceutical properties (ie, aqueous solubility and dissolution properties). ABSTRACTThe objective of this work is physicochemical characterization of nimesulide-cyclodextrin binary systems both in solution and solid state and to improve the dissolution properties of nimesulide (N) via complexation with α-, β, and γ-cyclodextrins (CDs). Detection of inclusion complexation was done in solution by means of phase solubility analysis, mass spectrometry, and 1 H nuclear magnetic resonance ( 1 H-NMR) spectroscopic studies, and in solid state using differential scanning calorimetry (DSC), powder xray diffractometry (X-RD), scanning electron microscopy (SEM), and in vitro dissolution studies. Phase solubility, mass spectrometry and 1 H-NMR studies in solution revealed 1:1 M complexation of N with all CDs. A true inclusion of N with β-CD at 1:2 M in solid state was confirmed by DSC, powder X-RD and SEM studies. Dissolution properties of N-CD binary systems were superior when compared to pure N.

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“…The solution is cooled and complex crystals occur. The crystals are washed with organic solvent and then dried at 50°C [11,13]. The co-precipitation technique has previously applied for encapsulation of drugs such as oxaprozin [14] and trans-anethole (major component of anise and fennel essential oils) [15].…”

Section: Co-precipitation Methodsmentioning

confidence: 99%

Inclusion complex formation of cyclodextrin with its guest and their applications

Cheirsilp¹,

Rakmai²

2017

Biol Eng Med

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Cyclodextrin (CD) are cyclic oligosaccharides consisting of glucopyranosyl units linked by α-(1,4) bonds. The widely used natural cyclodextrins are α-, β-and γ-cyclodextrin consisting of 6, 7 and 8 glucopyranose units, respectively. The cyclodextrin molecules have a unique structure with a hydrophobic cavity and a hydrophilic surface which can form inclusion complex with a wide variety of guests. The use of cyclodextrins and their derivatives for the encapsulation of bioactive compounds can protect the compounds from environmental conditions and improve the aqueous solubility for increasing their capacity to functionalize the products. In some cases, there is a need to enhance water solubility of β-cyclodextrin by adding the hydroxyalkyl groups on the β-cyclodextrin surface. This review aimed to summarize the method for inclusion complex formation of cyclodextrin with its guests and its applications. Table 1. The cyclodextrin molecules have a unique structure with a hydrophobic cavity and a hydrophilic surface in which a guest molecule can be entrapped. Cyclodextrin can form inclusion complex with a wide variety of solid, liquid and gaseous compounds. Complex formation is a dimensional, geometrically limited fit, between cyclodextrin cavity and the guest molecule [2].Generally, hydrophobic molecules have greater affinity for the cyclodextrin cavity when they are in water solution. Moreover, the encapsulation changes the physical and chemical properties of the guests, such as solubility and stability. Therefore, cyclodextrins are suitable for application in food and flavors, pharmaceutical products, cosmetic, agriculture and chemical industries. Cyclodextrins can link specifically to other cyclodextrins (covalent or noncovalent). Because of this property, cyclodextrins can be used as building blocks for the construction of supramolecular complexes. Building blocks which cannot be prepared by common methods can be applied, such as separation of complex mixtures of molecules and enantiomers [3]. Cyclodextrins are produced by reacting gelatinized starch with the enzyme cyclodextrin glucosyltransferase (CGTase) as a result of intramolecular transglycosylation reaction from degradation of starch. Inclusion complex formationCyclodextrins have an internal non-polar hole and hydroxyl groups placed on the surface, the inclusion of hydrophobic compounds takes place mainly by hydrophobic interactions between guest molecules and the walls of cyclodextrin cavity [5]. However, other forces, such as van der Walls and dipole-dipole interactions, may be involved in the binding of the guest. Despite the number of factors and different forces involved in the complexation with cyclodextrins, the production of complexes is a rather simple process. There are several methods to obtain cyclodextrin-guest complexes depending on the properties of the guest and the nature of the chosen cyclodextrin. Kneading methodKneading technique is suitable for poorly water-soluble guests, because the guest is dissolved slowly during the forma...

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Pharmaceutical Uses of Cyclodextrins and Derivatives

Cited by 139 publications

References 34 publications

Improved Pharmacokinetics of Aceclofenac Immediate Release Tablets Incorporating ist Inclusion Complex with Hydroxypropyl-β-Cyclodextrin

Improved Pharmacokinetics of Aceclofenac Immediate Release Tablets Incorporating ist Inclusion Complex with Hydroxypropyl-β-Cyclodextrin

Physicochemical characterization and dissolution properties of nimesulide-cyclodextrin binary systems

Inclusion complex formation of cyclodextrin with its guest and their applications

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