Formation of Hydroxyl-Amide Solid Dispersion Involving Azithromycin and Chitosan-Alginate Biopolymer to Increase the Dissolution Rate of Azithromycin
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Keywords:
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Co-grinding, Solid-dispersion, Azithromycin, Chitosan, Alginate
Abstract
Research to increase the solubility of active pharmaceutical ingredients is usually conducted by reducing the particle size. This research is one side that used the solid dispersion systems to increase solubility, especially on macrolide antibiotics for which there is still little information. The co-grinding technique on azithromycin-chitosan-alginate was chosen to produce a solid dispersion system. The parameters observed were changes in crystal structure, FTIR spectral patterns, morphological changes, and dissolution profile changes. The results of this research showed a change in the pattern of X-diffraction of azithromycin, physical interaction between azithromycin and the polymer, changes in the image of surface of solid dispersions, the solubility of solid dispersions in simulated-intestinal-fluid (SIF) solutions, and an increase in the dissolution rate of azithromycin indicating that the co-grinding technique to produce solid dispersions can increase the solubility of azithromycin.
References
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Garbacz, P., & Wesolowski, M. (2020). Benzodiazepines co-crystals screening using FTIR and Raman spectroscopy supported by differential scanning calorimetry. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 234.
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Vangala, V. R., Chow, P. S., & Tan, R. B. H. (2012). Co-crystals and co-crystal hydrates of the antibiotic nitrofurantoin: Structural studies and physicochemical properties. Crystal Growth and Design, 12(12).
Wang, C., Jiang, X., Zhang, X., Xu, Y., Li, L., Li, X., Wang, S., Shi, P., Gao, X., Liu, Z., Clark, W. D., & Cao, Y. (2023). A novel solvent-free co-grinding preparation improves curcumin bioavailability in healthy volunteers: A single-center crossover study. Heliyon, 9(1).
Wu, X., Wang, Y., Xue, J., Liu, J., Qin, J., Hong, Z., & Du, Y. (2020). Solid phase drug-drug pharmaceutical co-crystal formed between pyrazinamide and diflunisal: Structural characterization based on terahertz/Raman spectroscopy combining with DFT calculation. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 234.
Yuan, Y., Liu, D., Xiang, R., Li, Z., Zhang, M., Zhao, J., Fan, B., Li, C., Niu, D., & Ren, J. (2021). Advances in biodegradation of macrolide antibiotics. In Shengwu Gongcheng Xuebao/Chinese Journal of Biotechnology (Vol. 37, Issue 9).
Bhalani, D. V., Nutan, B., Kumar, A., & Singh Chandel, A. K. (2022). Bioavailability Enhancement Techniques for Poorly Aqueous Soluble Drugs and Therapeutics. In Biomedicines (Vol. 10, Issue 9).
Blumenberg, V., Schubert, M.-L., Zamir, E., Schmidt, S., Rohrbach, R., Waldhoff, P., Bozic, D., Pock, H., Elinav, E., Schmidt, C., Buecklein, V., Müller-Tidow, C., Dreger, P., von Bergwelt, M., Schmitt, M., Subklewe, M., & Stein-Thöringer, C. (2020). Antibiotic Therapy and Low Gut Microbiome Diversity Is Associated with Decreased Response and High Toxicity in BCP-ALL and DLBCL Patients after Treatment with CD19. CAR T-Cells. Blood, 136(Supplement 1).
Bol’shakov, M. N., Lebedeva, G. K., Marfichev, A. Y., Gofman, I. V., Rudaya, L. I., Sokolova, I. M., Chigirev, D. A., & Ramsh, S. M. (2022). Highly Heat-Resistant Poly(Amido Hydroxy Amides) with Increased Elongation at Break and Photosensitive Formulations Based on Them. Russian Journal of Applied Chemistry, 95(4).
Brennan, D. J., White, J. E., & Brown, C. N. (1998). High-barrier poly(hydroxy amide ethers): Effect of polymer structure on oxygen transmission rates. 31. Macromolecules, 31(23).
Echeverría-Esnal, D., Martin-Ontiyuelo, C., Navarrete-Rouco, M. E., De-Antonio Cuscó, M., Ferrández, O., Horcajada, J. P., & Grau, S. (2021). Azithromycin in the treatment of COVID-19: a review. In Expert Review of Anti-Infective Therapy (Vol. 19, Issue 2).
Gaglioti, K., Chierotti, M. R., Grifasi, F., Gobetto, R., Griesser, U. J., Hasa, D., & Voinovich, D. (2014). Improvement of the water solubility of tolfenamic acid by new multiple-component crystals produced by mechanochemical methods. CrystEngComm, 16(35).
Garbacz, P., & Wesolowski, M. (2020). Benzodiazepines co-crystals screening using FTIR and Raman spectroscopy supported by differential scanning calorimetry. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 234.
Jafari Ansaroudi, H. R., Vafaie-Sefti, M., Masoudi, S., Jafari Behbahani, T., & Jafari, H. (2013). Study of the morphology of wax crystals in the presence of ethylene-co-vinyl acetate copolymer. Petroleum Science and Technology, 31(6).
Jednačak, T., Mikulandra, I., & Novak, P. (2020). Advanced methods for studying structure and interactions of macrolide antibiotics. In International Journal of Molecular Sciences (Vol. 21, Issue 20).
Jiang, L., Huang, Y., Zhang, Q., He, H., Xu, Y., & Mei, X. (2014). Preparation and solid-state characterization of dapsone drug-drug co-crystals. Crystal Growth and Design, 14(9).
Khan, F. M., Ahmad, M., & Idrees, H. A. (2020). Simvastatin-nicotinamide co-crystals: Formation, pharmaceutical characterization and in vivo profile. Drug Design, Development and Therapy, 14.
Khantri, H., Hussain, M. S., & Tyagi, S. (2022). Solubility Enhancement Techniques: An Overview. World Journal of Pharmaceutical Research, 11(5).
Kim, J., & Ulrich, J. (2022). Dissolution and Growth Kinetics and the Rate-Controlling Step in Transformation of Amorphous to Crystalline Phase Using Antisolvent Crystallization. Industrial and Engineering Chemistry Research, 61(39).
Lu, Y., Lin, M., Zong, J., Zong, L., Zhao, Z., Wang, S., Zhang, Z., & Han, M. (2020). Highly bioavailable curcumin preparation with a co-grinding and solvent-free process. Food Science and Nutrition, 8(12).
Mardiyanto, Untari B., Fithri A. N., Mara A., Aprianto A.A., N. G. A. (2022). The Enhancement Solubility and Stability of Erythromycin Formatted in Solid Lipid Nanoparticles by Utilizing PVA as Stabilizer. Science and Technology Indonesia, 7(2), 195–201.
Mardiyanto, Untari, B., Mara, A., Sinulingga, S., Syarif, N., & Ningsih, G. E. (2022). Formulation and Evaluation of Solid Lipid Nanoparticles Loading Erythromycin Ethylsuccinate by Heating Emulsification and Homogenization Methods. Science and Technology Indonesia, 7(3).
Myers, A. G., & Clark, R. B. (2021). Discovery of Macrolide Antibiotics Effective against Multi-Drug Resistant Gram-Negative Pathogens. Accounts of Chemical Research, 54(7).
Ngilirabanga, J. B., & Samsodien, H. (2021). Pharmaceutical co‐crystal: An alternative strategy for enhanced physicochemical properties and drug synergy. Nano Select, 2(3).
Nugrahani, I., & Parwati, R. D. (2021). Challenges and progress in nonsteroidal anti-inflammatory drugs co-crystal development. In Molecules (Vol. 26, Issue 14).
O’Malley, C., McArdle, P., & Erxleben, A. (2021). Crystallization from the Gas Phase: Morphology Control, Co-Crystal and Salt Formation.
Rajbhar, P., Sahu, A. K., Gautam, S. S., Prasad, R. K., Singh, V., & Nair, S. K. (2016). Formulation and Evaluation of Clarithromycin Co- Crystals Tablets Dosage Forms to Enhance the Bioavailability. The Pharma Innovation Journal TPI, 5(56).
Rekdal, M., Pai, A., Choudhari, R., & Sathyanarayana, M. B. (2018). Applications of co-crystals in pharmaceutical drugs. In Systematic Reviews in Pharmacy (Vol. 9, Issue 1).
Savjani, K. T., Gajjar, A. K., & Savjani, J. K. (2012). Drug Solubility: Importance and Enhancement Techniques. ISRN Pharmaceutics, 2012.
Sharma, B., Ubaghs, L., Keul, H., Höcker, H., Loontjens, T., & Van Benthem, R. (2004). Microstructure and properties of poly(amide urethane)s: Comparison of the reactivity of α-hydroxy-ω-O-phenyl urethanes and α-hydroxy-ω-O-hydroxyethyl urethanes. Macromolecular Chemistry and Physics, 205(11).
Sun, J., Jia, L., Lin, B., Wang, Y., & Gong, J. (2021). Research advances of drug-drug co-crystals. In Huagong Xuebao/CIESC Journal (Vol. 72, Issue 2).
Untari, B., Wijaya, D. P., Mardiyanto, M., Herlina, H., Angraeni, V., & Firana, A. (2019). Physical Interaction Of Chitosan-Alginate Entrapping Extract Of Papaya Leaf And Formation Of Submicron Particles Dosage Form. Science and Technology Indonesia, 4(3).
Vangala, V. R., Chow, P. S., & Tan, R. B. H. (2012). Co-crystals and co-crystal hydrates of the antibiotic nitrofurantoin: Structural studies and physicochemical properties. Crystal Growth and Design, 12(12).
Wang, C., Jiang, X., Zhang, X., Xu, Y., Li, L., Li, X., Wang, S., Shi, P., Gao, X., Liu, Z., Clark, W. D., & Cao, Y. (2023). A novel solvent-free co-grinding preparation improves curcumin bioavailability in healthy volunteers: A single-center crossover study. Heliyon, 9(1).
Wu, X., Wang, Y., Xue, J., Liu, J., Qin, J., Hong, Z., & Du, Y. (2020). Solid phase drug-drug pharmaceutical co-crystal formed between pyrazinamide and diflunisal: Structural characterization based on terahertz/Raman spectroscopy combining with DFT calculation. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 234.
Yuan, Y., Liu, D., Xiang, R., Li, Z., Zhang, M., Zhao, J., Fan, B., Li, C., Niu, D., & Ren, J. (2021). Advances in biodegradation of macrolide antibiotics. In Shengwu Gongcheng Xuebao/Chinese Journal of Biotechnology (Vol. 37, Issue 9).
Authors
Mardiyanto, Untari, B., Mara, A., & Ferdiansyah, D. F. (2023). Formation of Hydroxyl-Amide Solid Dispersion Involving Azithromycin and Chitosan-Alginate Biopolymer to Increase the Dissolution Rate of Azithromycin. Science and Technology Indonesia, 8(4), 647–653. https://doi.org/10.26554/sti.2023.8.4.647-653
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