ENHANCEMENT OF SOLUBILITY AND DISSOLUTION RATE OF ACETYLSALICYLIC ACID VIA CO-CRYSTALLIZATION TECHNIQUE: A NOVEL ASA-VALINE COCRYSTAL

SHANTHALA H. K.; JAYAPRAKASH H. V.; MUNIGANTI RADHAKRISHNA; JASWANTH GOWDA B. H.; KARTHIKA PAUL; S. J. SHANKAR; MOHAMMED GULZAR AHMED; SANJANA A.

doi:10.22159/ijap.2021v13i1.40054

Authors

SHANTHALA H. K. Department of Chemistry, Sri Siddhartha Academy of Higher Education, Tumkur, India 572107
JAYAPRAKASH H. V. Department of Chemistry, Sri Siddhartha Institute of Technology, Tumkur, India 572105
MUNIGANTI RADHAKRISHNA Department of Chemistry, Sri Siddhartha Academy of Higher Education, Tumkur, India 572107
JASWANTH GOWDA B. H. Department of Pharmaceutics, Yenepoya Pharmacy College and Research Centre, Yenepoya (Deemed to be University), Mangaluru, India 575018
KARTHIKA PAUL Department of Pharmaceutical Sciences, Vivekananda College of Pharmacy, Dr. Rajkumar Road, Rajajinagar 2nd Stage, Bengaluru, India 560055
S. J. SHANKAR Department of Pharmaceutical Sciences, Vivekananda College of Pharmacy, Dr. Rajkumar Road, Rajajinagar 2nd Stage, Bengaluru, India 560055
MOHAMMED GULZAR AHMED Department of Pharmaceutics, Yenepoya Pharmacy College and Research Centre, Yenepoya (Deemed to be University), Mangaluru, India 575018
SANJANA A. Department of Pharmaceutics, Yenepoya Pharmacy College and Research Centre, Yenepoya (Deemed to be University), Mangaluru, India 575018,

DOI:

https://doi.org/10.22159/ijap.2021v13i1.40054

Keywords:

Acetylsalicylic acid, Valine, Co-crystallization, Solvent evaporation technique, Solubility enhancement, Dissolution rate, Cocrystals, Powder x-ray diffraction, Differential scanning calorimetry

Abstract

Objective: This study aims to synthesize acetylsalicylic acid (ASA) cocrystals using valine as a coformer via a co-crystallization technique to increase the solubility and dissolution rate of ASA.

Methods: The ASA-valine cocrystal (1:1 molar ratio) was prepared using the solvent evaporation technique with ethanol: water (50:50). The cocrystal was characterized using Fourier transform infrared spectroscopy (FT-IR), Differential scanning calorimetry (DSC), Powder X-ray diffraction (PXRD), Scanning electron microscopy (SEM), melting point to confirm the formation of cocrystal. The evaluation of cocrystal was done by drug content determination, solubility and dissolution studies.

Results: The prepared cocrystal was successfully confirmed for the formation of a hydrogen bond. The melting point of prepared cocrystal was decreased compared to pure ASA and valine, which indicated the formation of a new crystalline form. The FT-IR studies showed the formation of a new hydrogen bond by shifting the-O-H,-C=O and-N-H functional groups. SEM studies ensured that the prepared cocrystals were in needle-like appearance. Finally, DSC and PXRD studies were also indicated the successful formation of ASA-valine cocrystal. The drug release of cocrystal was found to be 100% at 60^th min. Where in the case of pure ASA and marketed product of ASA exhibited the dissolution rate of 59% and 69% at 60^th min respectively.

Conclusion: The co-crystallization technique can be adopted as the best strategy to increase the solubility and dissolution rate of BCS class 2 drugs. Therefore the prepared ASA-valine cocrystal can be a greater alternative to increase the solubility and dissolution rate compared with pure and marketed ASA.

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References

Taylor D. The pharmaceutical industry and the future of drug development. Pharmaceuticals in the Environment; 2015. p. 1-33. DOI:10.1039/9781782622345-00001.

Singh A, Worku ZA, Van den Mooter G. Oral formulation strategies to improve solubility of poorly water-soluble drugs. Expert Opin Drug Delivery 2011;8:1361-78.

Kalepu S, Nekkanti V. Insoluble drug delivery strategies: review of recent advances and business prospects. Acta Pharm Sin B 2015;5:442-53.

Shankar SJ, Gowda BHJ, Akshatha RS, Metikurki B, Rehamathulla M. A review on the role of nanocrystals and nanosuspensions in drug delivery systems. Int J Appl Pharm 2019;12:10-6.

Cherniakov I, Domb AJ, Hoffman A. Self-nano-emulsifying drug delivery systems: an update of the biopharmaceutical aspects. Expert Opin Drug Delivery 2015;12:1121-33.

Thakuria R, Delori A, Jones W, Lipert MP, Roy L, Rodriguez Hornedo N. Pharmaceutical cocrystals and poorly soluble drugs. Int J Pharm 2013;453:101-25.

Kuminek G, Cao F, Bahia de Oliveira da Rocha A, Gonçalves Cardoso S, Rodriguez Hornedo N. Cocrystals to facilitate delivery of poorly soluble compounds beyond-rule-of-5. Adv Drug Delivery Rev 2016;101:143-66.

Domingos S, Andre V, Quaresma S, Martins IC, Minas da Piedade MF, Duarte MT. New forms of old drugs: improving without changing. J Pharm Pharmacol 2015;67:830-46.

Chadha R, Saini A, Arora P, Bhandari S. Pharmaceutical cocrystals: a novel approach for oral bioavailability enhancement of drugs. Crit Rev Ther Drug Carrier Syst 2012;29:183-218.

Seddon KR, Zaworotko M. Crystal engineering: the design and application of functional solids, Kluwer Academic Publishers, The Netherlands; 1999.

Yamamoto K, Kojima T, Karashima M, Ikeda Y. Physicochemical evaluation and developability assessment of co-amorphouses of low soluble drugs and comparison to the co-crystals. Chem Pharm Bull 2016;64:1739-46.

Vioglio CP, Chierotti MR, Gobetto R. Pharmaceutical aspects of salt and cocrystal forms of APIs and characterization challenges. Adv Drug Delivery Rev 2017;117:86-110.

Childs SL, Stahly GP, Park A. The salt-cocrystal continuum: the influence of crystal structure on ionization state. Mol Pharm 2007;4:323-38.

Grothe E, Meekes H, Vlieg E, Horst JH, Gelder R. Solvates, salts, and cocrystals: a proposal for a feasible classification system. Cryst Growth Des 2016;16:3237-43.

Nie H, Byrn SR, Zhou QT. Stability of pharmaceutical salts in solid oral dosage forms. Drug Dev Ind Pharm 2017;43:1215-28.

Jones W, Motherwell WDS, Trask AV. Pharmaceutical cocrystals: an emerging approach to physical property enhancement. MRS Bull 2006;31:875-9.

Desiraju GR. Supramolecular synthons in crystal engineering-a new organicsynthesis. Angewandte Chemie International Edition 1995;34:2311-27.

Pindelska E, Sokal A, Kolodziejski W. Pharmaceutical cocrystals, salts and polymorphs: advanced characterization techniques. Adv Drug Delivery Rev 2017;117:111-46.

Douroumis D, Ross SA, Nokhodchi A. Advanced methodologies for cocrystal synthesis. Adv Drug Delivery Rev 2017;117:178-95.

Peltonen L. Practical guidelines for the characterization and quality control of pure drug nanoparticles and nano-cocrystals in the pharmaceutical industry. Adv Drug Delivery Rev 2018;131:101-15.

Gajda M, Nartowski KP, Pluta J, Karolewicz B. Continuous, one-step synthesis of pharmaceutical cocrystals via hot-melt extrusion from neat to matrix-assisted processing-state of the art. Int J Pharm 2019;558:426-40.

Shan N, Zaworotko MJ. The role of cocrystals in pharmaceutical science. Drug Discovery Today 2008;13:440-6.

Aitipamula S, Banerjee R, Bansal AK, Biradha K, Cheney ML, Choudhury AR, et al. Polymorphs, salts, and cocrystals: what's in a name? Cryst Growth Des 2012;12:2147-52.

Shankar SJ, Gowda JBH, Akshatha RS, Metikurki B. Co-crystallization: a novel approach to enhance the dissolution of poorly soluble drugs. Indo Am J Pharm Res 2019;9:3132-44.

Rodrigues M, Baptista B, Lopes JA, Sarraguça MC. Pharmaceutical cocrystallization techniques. Advances and challenges. Int J Pharm 2018;547:404-20.

Schultheiss N, Newman A. Pharmaceutical cocrystals and their physicochemical properties. Cryst Growth Des 2009;9:2950-67.

Kuminek G, Rodriguez Hornedo N, Siedler S, Rocha HV, Cuffini SL, Cardoso SG. How cocrystals of weakly basic drugs and acidic coformers might modulate solubility and stability. Chem Commun (Camb) 2016;52:5832-5.

Bell RG, Kott L. Chapter 17 regulatory considerations in dissolution and drug release of BCS class II and IV compounds, Poorly Soluble Drugs: Dissolution and Drug Release. Pan Stanford Publishing; 2017. p. 573-602.

Basavoju S, Bostrom D, Velaga SP. Indomethacin-saccharin cocrystal: design, synthesis and preliminary pharmaceutical characterization. Pharm Res 2008;25:530-41.

Aakeroy CB, Fasulo ME, Desper J. Cocrystal or salt: does it really matter? Mol Pharm 2007;4:317-22.

Brittain HG. Pharmaceutical cocrystals: the coming wave of new drug substances. J Pharm Sci 2013;102:311-7.

Babu JN, Nangia A. Solubility advantage of amorphous drugs and pharmaceutical cocrystals. Cryst Growth Des 2011;11:2662-79.

Bevill JM, Vlahova IP, Smit JP. Polymorphic cocrystals of nutraceutical compound p-coumaric acid with nicotinamide: characterization, relative solid-state stability, and conversion to alternate stoichiometries. Cryst Growth Des 2014;14:1438-48.

Awtry EH, Loscalzo J. Aspirin chapter 60. Circulation 2000;101:1206-18.

Born G, Patrono C. Antiplatelet drugs. Br J Pharmacol 2006; 147:241-51.

Oburn SM, Ray OA, MacGillivray LR. Elusive nonsolvated cocrystals of aspirin: two polymorphs with bipyridine discovered with the assistance of mechanochemistry. Cryst Growth Des 2018;18:2495-501.

Darwish S, Zeglinski J, Krishna GR, Shaikh R, Khraisheh M, Walker GM, et al. A new 1:1 drug-drug cocrystal of theophylline and aspirin: discovery, characterization, and construction of ternary phase diagrams. Cryst Growth Des 2018;18:7526-32.

Ray O. The generation of three novel aspirin co-crystals. Honors Theses at the University of Iowa; 2018. p. 1-22.

Kulkarni A, Shete S, Hol V, Bachhav R. Novel pharmaceutical cocrystal of telmisartan and hydrochlorothiazide. Asian J Pharm Clin Res 2020;13:104-12.

Budiman A, Husni P, Shafira, Alfauziah TQ. The development of glibenclamide-saccharin cocrystal tablet formulations to increase the dissolution rate of the drug. Int J Appl Pharm 2019;11:359-64.

Thenge R, Patel R, Kayande N, Mahajan N. Co-crystals of carvedilol: preparation, characterization and evaluation. Int J Appl Pharm 2020;12:42-9.

Budiman A, Megantara S, Apriliani A. Solid dosage form development of glibenclamide-aspartame cocrystal using the solvent evaporation method to increase the solubility of glibenclamide. Int J Appl Pharm 2019;11:150-4.

Raghuram R, Alam Ms, Prasad M, Khanduri CH. Pharmaceutical cocrystal of prulifloxacin with nicotinamide. Int J Appl Pharm 2014;6:180-4.

Zhang X, Sun F, Zhang T, Jia J, Su H, Wang C, et al. Three pharmaceuticals cocrystals of adefovir: syntheses, structures and dissolution study. J Mol Struct 2015;1100:395-400.

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.

Nechipadappu SK, Trivedi DR. Cocrystal of nutraceutical sinapic acid with active pharmaceutical ingredients ethenzamide and 2-chloro-4-nitrobenzoic acid: equilibrium solubility and stability study. J Mol Struct 2018;1171:898-905.

Hiendrawan S, Veriansyah B, Widjojokusumo E, Soewandhi SN, Wikarsa S, Tjandrawinata RR. Physicochemical and mechanical properties of paracetamol cocrystal with 5-nitroisophthalic acid. Int J Pharm 2016;497:106-13.