Interactions of .ALPHA.- and .BETA.-cyclodextrin with several non-steroidal antiinflammatory drugs in aqueou solution.

Hamada, Yoko; Nambu, Naoki; Nagai, Tsuneji

doi:10.1248/cpb.23.1205

Cited by 59 publications

(12 citation statements)

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“…There have been many studies in recent years concerning cyclodextrins (CyDs) with drugs in order to improve the stab characteristics o f the drug (1)(2)(3)(4)(5)(6)(7)(8)(9). The bioavailability of f the interaction o f lity or solubility urbiprofen has been obta manu 2688 MATSUYAMA, EL-GIZWAY, AND P E R R I N increased following complexation (8), a prostaglandin complex, suitable for oral use has been marketed and the possiblity of CyDs as an aid to peritoneal dialysis have been investigated (10).…”

Section: Introductionmentioning

confidence: 99%

Thermodynamics of Binding of Aromatic Amino Acids to α-, β- and γ-cyclodextrins

Matsuyama

El-Gizawy

Perrin

1987

Drug Development and Industrial Pharmacy

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The thermodynamics of the binding of aromatic amino acids, i.e., tryptophan, phenylalanine and tyrosine to a-, 6 -and r-cyclodextrin were investigated by microcalorimetry. Heat was evolved following the interaction o f tryptophan and tyrosine with (3-and 6-cyclodextrins but not with r-cyclodextrin.Phenylalanine only appeared to react with r-cyclodextrin. Human serum albumin contains these amino acids but the heat evolves following interaction with a and B-cyclodextrins was much lower than that evolved with the individual amino acids.No heat was evolved following the interaction of r-cyclodextrin with the albumin.

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Section: Introductionmentioning

confidence: 99%

Thermodynamics of Binding of Aromatic Amino Acids to α-, β- and γ-cyclodextrins

Matsuyama

El-Gizawy

Perrin

1987

Drug Development and Industrial Pharmacy

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“…Since IDM is, however, practically insoluble (ca. 2.5 mg/ml) in water, cyclodextrins, 8,9) poly(amidoamine) dendrimers, 10) and several additives 11) have been utilized to improve its dissolution. Furthermore, skin permeation of IDM was enhanced by the complexation of additives with L-menthol 12) or smectite.…”

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confidence: 99%

Molecular Complex Consisting of Two Typical External Medicines: Intermolecular Interaction between Indomethacin and Lidocaine

Umeda

Fukami

Furuishi

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Molecular complexes have been studied to improve the physico-chemical properties of drugs for the past half century. Higuchi et al. reported that caffeine formed complexes with benzoic acid and various benzoate derivative esters in solution.1) They attempted the first quantitative evaluation regarding the molecular association responsible for the existence of these complexes and the effect on chemical stability. The complexation of some local anesthetic esters such as benzocaine,2) procaine, 3) and lidocaine 4) (LDC) with caffeine was also attempted to inhibit the hydrolysis of the ester group on these drugs in aqueous solution. To improve chemical stability and/or increase solubility, such molecular coupling, which is not covalent bonding, has been extensively investigated, for example, riboflavin-nicotinamide, 5) ampicillin-benzaldehyde, 6) and iodine-polyvinyl pyrrolidone. 7)Indomethacin (IDM), a non-steroidal anti-inflammatory drug (NSAID), has been widely used to treat tendovaginitis, arthritis, and muscle pain as an ointment, cream, gel and adhesive plaster. Since IDM is, however, practically insoluble (ca. 2.5 mg/ml) in water, cyclodextrins, 8,9) poly(amidoamine) dendrimers, 10) and several additives 11) have been utilized to improve its dissolution. Furthermore, skin permeation of IDM was enhanced by the complexation of additives with L-menthol 12) or smectite. 13)LDC topical systems are used to relieve the pain and discomfort associated with herpes zoster virus infections of the skin. Our previous study using Neurometer ® demonstrated that the application of a 9% LDC ointment decreased sensory nerve function in 12 volunteers. Nevertheless, pain relief was not achieved efficiently, because the hydrochloride salt of LDC did not sufficiently penetrate the skin tissue.14) Accordingly, the LDC ointment was reformulated by adding IDM which was expected to heal the inflamed region, because there is no commercially available external medicine consisting of LDC and IDM. In a preliminary study, we obtained a reconstituted viscous paste from IDM and LDC kneaded with an appropriate amount of water.In this study, the intermolecular interaction between IDM and LDC was examined and the formation of a complex was confirmed using thermal analysis, a polarized microscope with a hot stage, fast-atom bombardment (FAB)-MS, phasesolubility techniques, IR, and 1 H-NMR. Finally, the molecular structure of the novel complex in aqueous solution was estimated. ExperimentalMaterials IDM and LDC were of reagent grade and purchased from Wako Pure Chemical Industries Ltd. (Osaka, Japan). All other chemicals and solvents were of reagent grade and used without further purification.Preparation of the IDM and LDC Complex An equimolar mixture of IDM and LDC was kneaded with an appropriate amount of distilled water using an agate mortar and pestle for 20 min. Then the milled mixture was dried at room temperature under reduced pressure overnight.Determination of IDM and LDC IDM, LDC, and the kneaded mixture were subjected to a HPLC analysis...

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“…Todavia, estudos efetuados por diversos autores evidenciam que a molécula de IM sofre inclusão parcial na molécula de HP-β-CD, havendo, contudo, divergência quanto à parte da estrutura química da IM que é incluída na ciclodextrina. Na Figura 7 estão representadas as duas principais hipóteses de forma de inclusão: inclusão da parte do anel indol (Djedaïni et al, 1990) e inclusão da parte p-clorobenzeno, sendo esta última a que tem maiores defensores, fundamentada na sua dimensão (7 Å) e comprovada através de técnica de simulação do modelo molecular tipo Stuart e modelagem computacional, permitindo obter informação sobre a geometria e a estrutura dos compostos de inclusão (Backensfeld et al, 1990(Backensfeld et al, , 1991Hamada et al, 1975;Kurozumi et al, 1975;Lin et al, 1991;Redenti et al, 2001). O caráter lipofílico da IM favorece, também, a formação do complexo.…”

Section: Fundamentação Para a Utilização De Complexos De Inclusão De unclassified

Aspectos biofarmacêuticos da formulação de medicamentos para neonatos: fundamentos da complexação de indometacina com hidroxipropil-beta-ciclodextrina para tratamento oral do fechamento do canal arterial

Rama¹,

Veiga²,

Figueiredo³

et al. 2005

Rev. Bras. Cienc. Farm.

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INTRODUÇÃOA investigação farmacêutica tem como intuito o desenvolvimento de novos agentes terapêuticos direcionados à resolução de situações clínicas, integrando conhecimentos pluridisciplinares.A prática de cuidados farmacêuticos possibilita a identificação de situações clínicas para as quais os recursos terapêuticos existentes não são os adequados. Fazer parte da equipe de saúde de uma unidade de cuidados intensivos de neonatologia é um desafio para o farmacêu-tico clínico, confrontado com a necessidade de dar resposta aos problemas biofarmacêuticos decorrentes da anatomofisiologia e das patologias inerentes àquele gru- Unitermos• Indometacina• Hidroxipropil-β-ciclodextrina• Recém-nascidos• Canal arterial

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Interactions of .ALPHA.- and .BETA.-cyclodextrin with several non-steroidal antiinflammatory drugs in aqueou solution.

Cited by 59 publications

References 0 publications

Thermodynamics of Binding of Aromatic Amino Acids to α-, β- and γ-cyclodextrins

Thermodynamics of Binding of Aromatic Amino Acids to α-, β- and γ-cyclodextrins

Molecular Complex Consisting of Two Typical External Medicines: Intermolecular Interaction between Indomethacin and Lidocaine

Aspectos biofarmacêuticos da formulação de medicamentos para neonatos: fundamentos da complexação de indometacina com hidroxipropil-beta-ciclodextrina para tratamento oral do fechamento do canal arterial

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