Identification of Candesartan Cilexetil-L-Arginine Co-amorphous Formation and Its Solubility Test
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Submitted
26 November 2021
Published
28 February 2022
Keywords:
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Co-amorphous, Candesartan cilexetil, L-Arginine, Liquid-assisted grinding, Solubility
Abstract
The formation of co-amorphous is one alternative that can be attempted to enhance the solubility of drugs. The study aimed to identify the co-amorphous formation between candesartan cilexetil (CAN) and l-arginine (ARG) and to know its effect on the solubility and dissolution rate of candesartan cilexetil. Initial prediction of co-crystal formation was undertaken by observing differences in crystal morphology between the candesartan cilexetil-l-arginine (CAN-ARG) mixture and each of its initial components due to crystallization in ethanol. The CAN-ARG co-amorphous was produced by the liquid-assisted grinding (LAG) method with the same molar ratio of the CAN and ARG mixture using ethanol as solvent. The co-amorphous formation of CAN-ARG was identified by powder X-ray diffraction (PXRD) and differential scanning calorimetry (DSC) methods. The solubility and dissolution test was performed to know the impact of the co-amorphous CAN-ARG formation. The PXRD pattern of CAN-ARG of LAG result showed a very low peak intensity compared to pure CAN and ARG. The DSC thermogram of the CAN-ARG LAG result does not show any sharp endothermic peaks. The PXRD and DSC results reveal that CAN and ARG can form co-amorphous. The solubility and dissolution rate of candesartan cilexetil in co-amorphous CAN-ARG was better than that of pure CAN. It can be concluded, liquid-assisted grinding of CAN-ARG mixture is identified to form co-amorphous which has an impact on increasing the solubility and dissolution rate of candesartan cilexetil.
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References
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29. Hancoock BC, Zografi G. Characteristics and significance of the amorphous state in pharmaceutical systems. J Pharm Sci. 1997;86(1):1–12. doi:10.1021/js9601896
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31. Figueroa-campos A, Sánchez-Dengra B, Merino V, Dahan A, González-Álvarez I, García-Arieta A, et al. Candesartan cilexetil in vitro–in vivo correlation: predictive dissolution as a development tool. Pharmaceutics. 2020;12(7):633. doi:10.3390/pharmaceutics12070633
2. Newman A, Reutzel-Edens SM, Zogra G. Coamorphous active pharmaceutical ingredient-small molecule mixtures: considerations in the choice of coformers for enhancing dissolution and oral bioavailability. J Pharm Sci. 2018;107(1):5-17. doi:10.1016/j.xphs.2017.09.024
3. Pandi P, Bulusu R, Kommineni N, Khan W, Singh M. Amorphous solid dispersions: An update for preparation, characterization, mechanism on bioavailability, stability, regulatory considerations and marketed products. Int J Pharm. 2020;586:119560. doi:10.1016/j.ijpharm.2020.119560
4. Jog R, Gokhale R, Burgess DJ. Solid state drug-polymer miscibility studies using the model drug ABT-102. Int J Pharm. 2016;509(1–2):285–95. doi:10.1016/j.ijpharm.2016.05.068
5. Skieneh JM, Sathisaran I, Dalvi SV, Rohani S. Co-amorphous form of curcumin-folic acid dihydrate with increased dissolution rate. Cryst Growth Des. 2017;17(12):6273–80. doi:10.1021/acs.cgd.7b00947
6. Shi Q, Moinuddin SM, Cai T. Advances in coamorphous drug delivery systems. Acta Pharm Sin B. 2019;9(1):19–35. doi:10.1016/j.apsb.2018.08.002
7. Karagianni A, Kachrimanis K, Nikolakakis I. Co-amorphous solid dispersions for solubility and absorption improvement of drugs: composition, preparation, characterization and formulations for oral delivery. Pharmaceutics. 2018;10(3):98. doi:10.3390/pharmaceutics10030098
8. Ranjan S, Devarapalli R, Kundu S, Vangala VR, Ghosh A, Reddy CM. Three new hydrochlorothiazide cocrystals: Structural analyses and solubility studies. J Mol Struct. 2017;1133:405–10. doi:10.1016/j.molstruc.2016.12.019
9. Nugrahani I, Jessica MA. Amino acids as the potential co-former for co-crystal development: a review. Molecules. 2021;26(11):3279. doi:10.3390/molecules26113279
10. Lenz E, Jensen KT, Blaabjerg LI, Knop K, Grohganz H, Löbmann K, et al. Solid-state properties and dissolution behaviour of tablets containing co-amorphous indomethacin-arginine. Eur J Pharm Biopharm. 2015;96:44-52. doi:10.1016/j.ejpb.2015.07.011
11. Petry I, Löbmann K, Grohganz H, Rades T, Leopold CS. In situ co-amorphisation of arginine with indomethacin or furosemide during immersion in an acidic medium – A proof of concept study. Eur J Pharm Biopharm. 2018;133:151-60. doi:10.1016/j.ejpb.2018.10.011
12. Löbmann K, Laitinen R, Grohganz H, Gordon KC, Strachan C, Rades T. Coamorphous drug systems: Enhanced physical stability and dissolution rate of indomethacin and naproxen. Mol Pharm. 2011;8(5):1919–28. doi:10.1021/mp2002973
13. Ojarinta R, Lerminiaux L, Laitinen R. Spray drying of poorly soluble drugs from aqueous arginine solution. Int J Pharm. 2017;532(1):289–98. doi:10.1016/j.ijpharm.2017.09.015
14. Ruponen M, Rusanen H, Laitinen R. Dissolution and permeability properties of co-amorphous formulations of hydrochlorothiazide. J Pharm Sci. 2020;109(7): 2252–61. doi:10.1016/j.xphs.2020.04.008
15. Aljohani M, Macfhionnghaile P, McArdle P, Erxleben A. Investigation of the formation of drug-drug cocrystals and coamorphous systems of the antidiabetic drug gliclazide. Int J Pharm. 2019;561:35–42. doi:10.1016/j.ijpharm.2019.02.024
16. Jung S, Choi I, Kim IW. Liquid-assisted grinding to prepare a cocrystal of adefovir dipivoxil thermodynamically less stable than its neat phase. Crystals. 2015;5(4):583–91. doi:10.3390/cryst5040583
17. Luo Y, Chen S, Zhou J, Chen J, Tian L, Gao W, et al. Luteolin cocrystals: Characterization, evaluation of solubility, oral bioavailability and theoretical calculation. J Drug Deliv Sci Technol. 2019;50:248–54. doi:10.1016/j.jddst.2019.02.004
18. Alatas F, Aprilliana M, Gozali D. The preparation and solubility of loratadine-fumaric acid binary mixture. Asian J Pharm Clin Res. 2017;10(1):331-4. doi:10.22159/ajpcr.2017.v10i1.15400
19. Haneef J, Chadha R. Drug-drug multicomponent solid forms: Cocrystal, coamorphous and eutectic of three poorly soluble antihypertensive drugs using mechanochemical approach. AAPS PharmSciTech. 2017;18(6):2279–90. doi:10.1208/s12249-016-0701-1
20. Moinuddin SM, Ruan S, Huang Y, Gao Q, Shi Q, Cai B, et al. Facile formation of co-amorphous atenolol and hydrochlorothiazide mixtures via cryogenic-milling: Enhanced physical stability, dissolution and pharmacokinetic profile. Int J Pharm. 2017;532(1):393-400. doi:10.1016/j.ijpharm.2017.09.020
21. Mithu MDSH, Ross SA, Hurt AP, Douroumis D. Effect of mechanochemical grinding conditions on the formation of pharmaceutical cocrystals and co-amorphous solid forms of ketoconazole – Dicarboxylic acid. J Drug Deliv Sci Technol. 2021;63:102508. doi:10.1016/j.jddst.2021.102508
22. Kasten G, Lobo L, Dengale S, Grohganz H, Rades T, Löbmann K. In vitro and in vivo comparison between crystalline and co-amorphous salts of naproxen-arginine. Eur J Pharm Biopharm. 2018;132:192–9. doi:10.1016/j.ejpb.2018.09.024
23. Zhang Y, Wang L, Dai J, Liu F, Li Y, Wu Z, et al. The comparative study of cocrystal/salt in simultaneously improving solubility and permeability of acetazolamide. J Mol Struct. 2019;1184:225-32. doi:10.1016/j.molstruc.2019.01.090
24. United States Pharmacopeia 40 National Formulary 35 [Internet]. Rockville (MA): United States Pharmacopeial Convention; 2017. p. 3156–7
25. Bowmaker GA. Solvent-assisted mechanochemistry. Chem Commun. 2013;49(4):334–48. doi:10.1039/c2cc35694e
26. Matsunaga H, Eguchi T, Nishijima K, Enomoto T, Sasaoki K, Nakamura N. Solid-state characterization of candesartan cilexetil (TCV-116): Crystal structure and molecular mobility. Chem Pharm Bull. 1999;47(2):182–6. doi:10.1248/cpb.47.182
27. Chen X, Li D, Zhang H, Duan Y, Huang Y. Sinomenine-phenolic acid coamorphous drug systems: Solubilization, sustained release, and improved physical stability. Int J Pharm. 2021;598:120389. doi:10.1016/j.ijpharm.2021.120389
28. de Campos DP, Silva-Barcellos NM, Lima RR, Savedra RML, Siqueira MF, Yoshida MI, et al. Polymorphic and quantum chemistry characterization of candesartan cilexetil: importance for the correct drug classification According to Biopharmaceutics Classification System. AAPS PharmSciTech. 2018;19(7):3019–28. doi:10.1208/s12249-018-1129-6
29. Hancoock BC, Zografi G. Characteristics and significance of the amorphous state in pharmaceutical systems. J Pharm Sci. 1997;86(1):1–12. doi:10.1021/js9601896
30. Huang Y, Zhang Q, Wang J-R, Lin K-L, Mei X. Amino acids as co-amorphous excipients for tackling the poor aqueous solubility of valsartan. Pharm Dev Technol. 2017;22(1):69–76. doi:10.3109/10837450.2016.1163390
31. Figueroa-campos A, Sánchez-Dengra B, Merino V, Dahan A, González-Álvarez I, García-Arieta A, et al. Candesartan cilexetil in vitro–in vivo correlation: predictive dissolution as a development tool. Pharmaceutics. 2020;12(7):633. doi:10.3390/pharmaceutics12070633
Authors
1.
Alatas F, Mutmainah ES, Ratih H, Sutarna TH, Soewandhi SN. Identification of Candesartan Cilexetil-L-Arginine Co-amorphous Formation and Its Solubility Test. Borneo J Pharm [Internet]. 2022Feb.28 [cited 2024Nov.21];5(1):27-34. Available from: https://journal.umpr.ac.id/index.php/bjop/article/view/2942
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