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Analysis of physicochemical properties of ternary systems of oxaprozin with randomly methylated-β-cyclodextrin and l-arginine aimed to improve the drug solubility.
J Pharm Biomed Anal. 2016 Sep 10; 129:350-358.JP

Abstract

The influence of l-arginine on the complexing and solubilizing power of randomly-methylated-β-cyclodextrin (RameβCD) towards oxaprozin, a very poorly soluble anti-inflammatory drug, was examined. The interactions between the components were investigated both in solution, by phase-solubility analysis, and in the solid state, by differential scanning calorimetry, FTIR and X-ray powder diffractometry. The morphology of the solid products was examined by Scanning Electron Microscopy. Results of phase-solubility studies indicated that addition of arginine enhanced the RameβCD complexing and solubilizing power of about 3.0 and 4.5 times, respectively, in comparison with the binary complex (both at pH≈6.8). The effect of arginine was not simply additive, but synergistic, being the ternary system solubility higher than the sum of those of the respective drug-CD and drug-arginine binary systems. Solid equimolar ternary systems were prepared by physical mixing, co-grinding, coevaporation and kneading techniques, to explore the effect of the preparation method on the physicochemical properties of the final products. The ternary co-ground product exhibited a dramatic increase in both drug dissolution efficiency and percent dissolved at 60min, whose values (83.6 and 97.1, respectively) were about 3 times higher than the sum of those given by the respective drug-CD and drug-aminoacid binary systems. Therefore, the ternary co-ground system with arginine and RameβCD appears as a very valuable product for the development of new more effective delivery systems of oxaprozin, with improved safety and bioavailability.

Authors+Show Affiliations

Department of Chemistry, School of Human Health Sciences, University of Florence, Via Schiff 6, Sesto Fiorentino I-50019, Florence, Italy.Department of Chemistry, School of Human Health Sciences, University of Florence, Via Schiff 6, Sesto Fiorentino I-50019, Florence, Italy.Department of Chemistry, School of Human Health Sciences, University of Florence, Via Schiff 6, Sesto Fiorentino I-50019, Florence, Italy.Department of Chemistry, School of Human Health Sciences, University of Florence, Via Schiff 6, Sesto Fiorentino I-50019, Florence, Italy. Electronic address: paola.mura@unifi.it.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27454086

Citation

Mennini, Natascia, et al. "Analysis of Physicochemical Properties of Ternary Systems of Oxaprozin With Randomly Methylated-β-cyclodextrin and L-arginine Aimed to Improve the Drug Solubility." Journal of Pharmaceutical and Biomedical Analysis, vol. 129, 2016, pp. 350-358.
Mennini N, Maestrelli F, Cirri M, et al. Analysis of physicochemical properties of ternary systems of oxaprozin with randomly methylated-β-cyclodextrin and l-arginine aimed to improve the drug solubility. J Pharm Biomed Anal. 2016;129:350-358.
Mennini, N., Maestrelli, F., Cirri, M., & Mura, P. (2016). Analysis of physicochemical properties of ternary systems of oxaprozin with randomly methylated-β-cyclodextrin and l-arginine aimed to improve the drug solubility. Journal of Pharmaceutical and Biomedical Analysis, 129, 350-358. https://doi.org/10.1016/j.jpba.2016.07.024
Mennini N, et al. Analysis of Physicochemical Properties of Ternary Systems of Oxaprozin With Randomly Methylated-β-cyclodextrin and L-arginine Aimed to Improve the Drug Solubility. J Pharm Biomed Anal. 2016 Sep 10;129:350-358. PubMed PMID: 27454086.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Analysis of physicochemical properties of ternary systems of oxaprozin with randomly methylated-β-cyclodextrin and l-arginine aimed to improve the drug solubility. AU - Mennini,Natascia, AU - Maestrelli,Francesca, AU - Cirri,Marzia, AU - Mura,Paola, Y1 - 2016/07/18/ PY - 2016/05/19/received PY - 2016/07/15/revised PY - 2016/07/16/accepted PY - 2016/7/26/entrez PY - 2016/7/28/pubmed PY - 2017/5/4/medline KW - Arginine KW - Dissolution rate KW - Oxaprozin KW - Phase-solubility diagrams KW - Randomly-methylated β-cyclodextrin KW - Ternary complexes SP - 350 EP - 358 JF - Journal of pharmaceutical and biomedical analysis JO - J Pharm Biomed Anal VL - 129 N2 - The influence of l-arginine on the complexing and solubilizing power of randomly-methylated-β-cyclodextrin (RameβCD) towards oxaprozin, a very poorly soluble anti-inflammatory drug, was examined. The interactions between the components were investigated both in solution, by phase-solubility analysis, and in the solid state, by differential scanning calorimetry, FTIR and X-ray powder diffractometry. The morphology of the solid products was examined by Scanning Electron Microscopy. Results of phase-solubility studies indicated that addition of arginine enhanced the RameβCD complexing and solubilizing power of about 3.0 and 4.5 times, respectively, in comparison with the binary complex (both at pH≈6.8). The effect of arginine was not simply additive, but synergistic, being the ternary system solubility higher than the sum of those of the respective drug-CD and drug-arginine binary systems. Solid equimolar ternary systems were prepared by physical mixing, co-grinding, coevaporation and kneading techniques, to explore the effect of the preparation method on the physicochemical properties of the final products. The ternary co-ground product exhibited a dramatic increase in both drug dissolution efficiency and percent dissolved at 60min, whose values (83.6 and 97.1, respectively) were about 3 times higher than the sum of those given by the respective drug-CD and drug-aminoacid binary systems. Therefore, the ternary co-ground system with arginine and RameβCD appears as a very valuable product for the development of new more effective delivery systems of oxaprozin, with improved safety and bioavailability. SN - 1873-264X UR - https://www.unboundmedicine.com/medline/citation/27454086/Analysis_of_physicochemical_properties_of_ternary_systems_of_oxaprozin_with_randomly_methylated_β_cyclodextrin_and_l_arginine_aimed_to_improve_the_drug_solubility_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0731-7085(16)30396-X DB - PRIME DP - Unbound Medicine ER -