CRYSTAL ENGINEERING OF ANTIVIRAL AGENT EFAVIRENZ FOR SOLUBILITY ENHANCEMENT
In the current study, we attempted to improve the physicochemical properties of antiviral drug efavirenz through the cocrystal synthesis. The neat grinding performed to study the effect of coformer-fumaric acid (FA) on solubility and dissolution of efavirenz, which can serve as the green cocrystal synthesis approach. The prepared cocrystals were characterized for characteristics like powder flow properties, aqueous saturation solubility, in vitro powder dissolution study. The synthesized cocrystals were characterized by Fourier transform infrared spectroscopy, differential scanning calorimetry, powder X-ray diffraction. The formation of a cocrystal of efavirenz and caffeine was confirmed by the characterization techniques which suggests the interactions between efavirenz and coformer-fumaric acid leads to cocrystal formation. The powder flow properties, solubility, and dissolution profile of efavirenz are significantly improved by its cocrystallization.
2. U.S. Department of Health and Human Services, Food and Drug Administration Center for Drug Evaluation and Research (CDER) Guidance for Industry Regulatory Classification of Pharmaceutical Co-Crystals. 2013.
3. Savjani JK. Co â€‘crystallizationâ€¯: An approach to improve the performance characteristics of active. Asian J Pharm. 2015;(July-September):147â€“51.
4. Bysouth SR, Bis JA, Igo D. Cocrystallization via planetary milling: Enhancing throughput of solid-state screening methods. Int J Pharm [Internet]. Elsevier B.V.; 2011;411(1â€“2):169â€“71. Available from: http://dx.doi.org/10.1016/j.ijpharm.2011.03.037
5. Apshingekar PP, Aher S, Kelly AL, Brown EC, Paradkar A. Synthesis of Caffeine / Maleic Acid Co-crystal by Ultrasound-assisted. J Pharm Sci [Internet]. Elsevier Ltd; 2016;106(1):66â€“70. Available from: http://dx.doi.org/10.1016/j.xphs.2016.09.009
6. Trask A V, Samuel WD, Jones W. Solvent-drop grindingâ€¯: green polymorph control of cocrystallisation. Chem Commun. 2004;2004:890â€“1.
7. Duarte I, Andrade R. Green production of cocrystals using a new solvent-free approach by spray congealing. Int J Pharm 2016; http://dx.doi.org/10.1016/j.ijpharm.2016.04.010
8. Berry DJ, Steed JW. Pharmaceutical cocrystals , salts and multicomponent systemsâ€¯; intermolecular interactions and property based design. Adv Drug Deliv Rev J. 2017
9. Chadha R, Arora P, Saini A, Jain DS. An Insight into Thermodynamic Relationship Between Polymorphic Forms of Efavirenz. J Pharm Pharm Sci. 2012;15(2):234â€“51.
10. Fandaruff C, Rauber GS, Andrea M. Araya-Sibaja RNP, Carlos EM de Campos HVR, Monti GA, Malaspina T, et al. Polymorphism of Anti-HIV Drug Efavirenzâ€¯: Investigations on Thermodynamic and Dissolution Properties Polymorphism of Anti-HIV Drug Efavirenzâ€¯: Investigations on Thermodynamic and Dissolution Properties. Cryst Growth Des. 2014;2014(14):4968âˆ’497.
11. Zaini E, Wahyu D, Octavia M, L Fitriani. Influence of Milling Process on Efavirenz Solubility. J Pharm Bioall Sci. 2017;9:22â€“5.
12. Koh PT, Chuah JN, Talekar M, Gorajana A, Garg S. Formulation Development and Dissolution Rate Enhancement of Efavirenz by Solid Dispersion Systems. Indian J Pharm Sci. 2013;75(3):291â€“301.
13. Rajurkar VG, Nagare AS, Vilas G. Tablet Formulation and Enhancement of Aqueous Solubility of Efavirenz by Solvent Evaporation Co-Crystal Technique. Med Chem (Los Angeles). 2015;S2:2.
14. Perlovich GL, Volkova T V, Bauer-brandl A. Towards an Understanding of the Molecular Mechanism of Solvation of Drug Moleculesâ€¯: A Thermodynamic Approach by Crystal Lattice Energy , Sublimation , and Solubility Exemplified by Paracetamol , Acetanilide , and Phenacetin. J Pharm Sci. 2006;95(10):2158â€“69.
15. Pawar J, Amin PD. Development of efavirenz cocrystals from stoichiometric solutions by spray drying technology Development of efavirenz cocrystals from stoichiometric solutions by spray drying technology. Mater Today Proc [Internet]. Elsevier Ltd; 2016;3(6):1742â€“51. Available from: http://dx.doi.org/10.1016/j.matpr.2016.04.069
16. Mohammad MA, Alhalaweh A, Velaga SP. Hansen solubility parameter as a tool to predict cocrystal formation. Int J Pharm [Internet]. Elsevier B.V.; 2011;407(1â€“2):63â€“71. Available from: http://dx.doi.org/10.1016/j.ijpharm.2011.01.030
17. Gadade DD, Pekamwar SS, Lahoti SR, Patni SD, Sarode MC. Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release. Marmara Pharm J. 2017;21(1).
18. Gadade D, Kulkarni D, Rathi P, Pekamwar S, Joshi S. Solubility Enhancement of Lornoxicam by Crystal Engineering. Indian J Pharm Sci. 2017;79(March):277â€“86.
19. Gadade D, Pekamwar S, Lahoti SR, Patni S, Sarode M. Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release. Marmara Pharm J. 2017;21(1).
20. Shewale S, Shete AS, Doijad RC, Kadam SS, Patil VA, Yadav A V. Formulation and Solid State Characterization of Nicotinamide-based Co- crystals of Fenofibrate. Indian J Pharm Sci. 2015;77(3):328â€“34.
21. Carvalho PS jr, Almeida LR, Neto JHA, Medina ACQD, Menezes ACS. Structural and Theoretical Investigation of Anhydrous 3 , 4 , 5- Triacetoxybenzoic Acid. PLoS One. 2016;11(6):1â€“12.
22. Aithal K, Pai A, Girish Pai A, Sathyanarayana MB. Preparation , Solid State Characterization of Etraverine Co-Crystals with Improved Solubility Preparation , Solid State Characterization of Etraverine. Lat Am J Pharm. 2017;36(5):972â€“9.
23. Hoguchi TK, A. C. PHASE-SOLUBILITY TECHNIQUES. Adv Chem Intrumentation. 1965;4:212â€“7.
24. Grossjohann C, Eccles KS, Maguire AR, Lawrence SE, Tajber L, Corrigan OI, et al. Characterisation, solubility and intrinsic dissolution behaviour of benzamide: Dibenzyl sulfoxide cocrystal. Int J Pharm [Internet]. Elsevier B.V.; 2012;422(1â€“2):24â€“32. Available from: http://dx.doi.org/10.1016/j.ijpharm.2011.10.016
25. Greenhalgh DJ, Williams AC, Timmins P, York P. Solubility parameters as predictors of miscibility in solid dispersions. J Pharm Sci. 1999;88(11):1182â€“90.
26. Pharmacopeia US. United State Pharmacopoeia 29-National Formulary-24. 2006th ed. United State Pharmacopoeia 29-National Formulary-24. Rockville: United States Pharmacopeial Convention; 2006. 3017 p.
27. Larkin P. Infrared and Raman Spectroscopy. Elsevier. 2011. 73-115 p.
28. Alves L, Soares M, de Albuquerque C, da Silva Ã‰, Vieira A, Fontes D, et al. Solid dispersion of efavirenz in PVP K-30 by conventional solvent and kneading methods. Carbohydr Polym j. 2014;104:166â€“74.
29. El-gizawy SA, Osman MA, Arafa MF, Maghraby GM El. Aerosil as a novel co-crystal co-former for improving the dissolution rate of hydrochlorothiazide. Int J Pharm [Internet]. Elsevier B.V.; 2015;478:773â€“8. Available from: http://dx.doi.org/10.1016/j.ijpharm.2014.12.037
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