Cyclodextrin Inclusion Complexes of Two Non-Steroidal Antiinflammatory Drugs and of an Analgesic Drug

Brown, SE; Coates, John H.; Easton, CJ; Lincoln, SF; Luo, Yen-Lin; Stephens, Akw

doi:10.1071/ch9910855

Cited by 24 publications

(4 citation statements)

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“…Ilić-Stojanović and collaborators developed the inclusion complex naproxen:2-hydroxypropyl-β-cyclodextrin which showed the increased naproxen photostability in a thirty-days period of daylight exposure [ 9 ]. The interactions between naproxen, ibuprofen and panadol in the inclusion complexes of α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin and dimethyl-β-cyclodextrin were investigated [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Semi-Crystalline Copolymer Hydrogels as Smart Drug Carriers: In Vitro Thermo-Responsive Naproxen Release Study

Ilić‐Stojanović

Nikolić

et al. 2021

Pharmaceutics

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In this study, poly(N-isopropylacrylamide-co-2-hydroxypropyl methacrylate) hydrogels were synthesized using free radical initiated copolymerization method. Four hydrogels with different cross-linker concentrations were prepared. Semi-crystalline, cross-linked copolymer networks were confirmed by FTIR, SEM and XRD analysis. Variation of swelling behaviour was monitored gravimetrically and thermo-responsiveness has been noticed. An application of synthesized thermo-responsive hydrogels as carriers for the modulated release of anti-inflammatory model drug was investigated. Moreover, naproxen loading into these hydrogels was also determined using FTIR, SEM and XRD techniques and release was analyzed using HPLC method at simulated physiological conditions. Swelling kinetic and mechanism of water transport, as well as diffusion of naproxen through the hydrogels were analyzed. Thus, the aim of this work was to study various compositions of obtained hydrogels and their possibility of application as a thermo-responsive carrier for prolonged naproxen release in order to evaluate as a potential candidate for drug carrier in future pharmaceutical applications.

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Section: Introductionmentioning

confidence: 99%

Semi-Crystalline Copolymer Hydrogels as Smart Drug Carriers: In Vitro Thermo-Responsive Naproxen Release Study

Ilić‐Stojanović

Nikolić

et al. 2021

Pharmaceutics

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“…The chemical shifts are downfield from TPS. The broader resonances observed in (f) and(9) are thought to be due to the higher viscosity of these solutions.…”

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confidence: 95%

Substituent effects and chiral discrimination in the complexation of benzoic, 4-methylbenzoic and (RS)-2-phenylpropanoic acids and their conjugate bases by β-cyclodextrin and 6^A-amino-6^A-deoxy-β-cyclodextrin in aqueous solution: potentiometric titration and¹H nuclear magnetic resonance spectroscopic study

Brown¹,

Coates²,

Duckworth³

et al. 1993

J. Chem. Soc., Faraday Trans.

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A potentiometric titration study in aqueous solution (I = 0.10 mol dm-3, KCI) of the complexation of benzoic, 4-methylbenzoic and (RS)-2-phenylpropanoic acids (HA) and their conjugate bases (A-) with Bcyclodextrin, BCD, and its substituted analogue, 6A-amino-6A-deoxy-~-cyclodextrin, BCDNH, , in which a primary hydroxy group is replaced by an amino group which may be protonated to produce a singly charged species, BCDNH; , is reported. At 298.2 K the stability constants for the complexes have the values (in dm3 mol-') shown in parentheses : benzoic acid * BCD (K, HA = 590 & 60) ; benzoate PCD (K, A = 60 f 10) ; benzoic acid * BCDNH; (K,,, = 340 f 30) ; benzoate . BCDNH; ( K ~A = 120 & 20) ; benzoate . BCDNH, (K3A = 50 f 20) ; 4-methylbenzoic acid -PCD (K, HA = 1680 & 90) ; Cmethylbenzoate -BCD (K,, = 110 f 1) ; 4-methylbenzoic acid * BCDNH; ( K 2 H A = 910 f 20); 4-methylbenzoate -BCDNH; ( K 2 A = 330 & 20); and 4-methylbenzoate . PCDNH, (K3A = 100 & 20).These data indicate that for a given cyclodextrin the guest carboxylic acids form complexes of higher stability than do their conjugate base analogues, and that BCDNH; forms more stable complexes with the conjugate bases than do BCD and PCDNH,. These trends are also observed for the complexation of (RS)-2-phenylpropanoic acid and (RS)-2-phenylpropanoate where the complexes indicated are characterised by the stability constants (in dm3 mol-') shown in parentheses: (RS)-2-phenylpropanoic acid. BCD ( K , R H A = 1090 k 30, K,,,, = 1010 f 40) ; (RS)-2-phenylpropanoate * PCD (K, , , = 63 f 8, K,,, = 52 & 5) ; (RS)-2-phenylpropanoic K,,, = 110 f 10); and (RS)-2-phenylpropanoate BCDNH, (K3,, = 36 f 6, K3,A = 13 & 7). These data also show that while K1,HA and K i s H A , and K , , , and KISA are indistinguishable for (RS)-2-phenylpropanoic acid * BCD and (RS)-2-phenylpropanoate * BCD, chiral discrimination is indicated by K,,HA > K2sHA for (RS)-2-phenylpropanoic acid BCDNH;, K,,, > KZSA for (RS)-2-phenylpropanoate -PCDNH; , and K3,, > KBSA for (RS)-2phenylpropanoate -BCDNH, . The ' H NMR spectra of the methyl groups of the enantiomers of (RS)-2-phenylpropanoic acid appear as two separate doublets, indicating chiral discrimination when complexed by BCD or BCDNH; , but such chiral discrimination is not observed for (RS)-2-phenylpropanoate when complexed by PCDNH; . The implications of these observations are discussed. acid * BCDNH; (K2RHA = 580 f 20, K~,HA = 480 & 10); (RS)-2-phenylpropanoate * BCDNH;

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“…The inclusion complex of naproxen with β-cyclodextrin increased the solubility and the drug release rate [9,10]. The interactions in inclusion complexes of α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin and dimethyl-β-cyclodextrin with naproxen, ibuprofen and panadol were examined [11]. The inclusion complexes of cyclodextrin and its derivatives were used to improve the physical and chemical properties of the drugs (solubility, vapor, odor, stability, etc.).…”

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confidence: 99%

The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

Ilić‐Stojanović¹,

Nikolić²,

Nikolić³

et al. 2015

Hem Ind

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The aim of this work was the preparation of the inclusion complex of naproxen with 2hydroxypropyl-β-cyclodextrin (HP-β-CD) in order to improve the physical and chemical properties of naproxen. The molecular inclusion complexes of naproxen with HP-β-CD were prepared by using the co-precipitation method in the solid state with the molar ratio of 1:1. The structure of the obtained complex was characterized by using FTIR, 1 H NMR, UV-Vis and XRD methods. The testing of naproxen photostability by the UV-Vis method indicated the degradation to aromatic ketone, 2-acetyl-6-methoxynaphthalene. FTIR analysis showed that the degradation has started 15 days after the exposure of naproxen to daylight while the inclusion complex of naproxen:2-hydroxypropyl-β-cyclodextrin was photostable for a period of 30 days.

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Cyclodextrin Inclusion Complexes of Two Non-Steroidal Antiinflammatory Drugs and of an Analgesic Drug

Cited by 24 publications

References 0 publications

Semi-Crystalline Copolymer Hydrogels as Smart Drug Carriers: In Vitro Thermo-Responsive Naproxen Release Study

Semi-Crystalline Copolymer Hydrogels as Smart Drug Carriers: In Vitro Thermo-Responsive Naproxen Release Study

The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

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