Assessment and Research on Recrystallization on Dexamethasone Polymorph by the Use of Gas Chromatography–Mass Spectrometry and Fourier Transform Infrared Spectroscopy
Abstract
The presence of more than one crystalline form of a medication is known as polymorphism. Polymorphs have the same molecular formula but varied physicochemical features, such as solubility, which impact the pharmacological effects in the body. This paper set out to investigate how processing conditions and solvent polarity affected the crystallization and physicochemical properties of Dexamethasone. Deep freezing, law temperature cooling (4C°), and room temperature were among the processing conditions used to prepare the crystals, which can have varying degrees of solvent polarity. Researchers looked for drug polymorphisms using microscopy and Fourier transform infrared spectroscopy. The results show that the physicochemical properties of crystals were affected by the solvents and processing conditions used to create them. FT-IR detected spectra that differed from one another. Varying the polarity of the solvent and the processing conditions can lead to crystals with varying characteristics.
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Dang, T. T.; Bratlie, K. M.; Bogatyrev, S. R.; Chen, X. Y.; Langer, R.; Anderson, D. G. Biomaterials 2011, 32, 4464−4470.
Hickey, T.; Kreutzer, D.; Burgess, D. J.; Moussy, F. J. Biomed. Mater. Res. 2002, 61, 180−187.
Patil, S. D.; Papadimitrakopoulos, F.; Burgess, D. J. Diabetes Technol. Ther. 2004, 6, 887−97.
Bhardwaj, U.; Sura, R.; Papadimitrakopoulos, F.; Burgess, D. J. J. Diabetes Sci. Technol. 2007, 1, 8−17.
Anderson, J. M.; Rodriguez, A.; Chang, D. T. Semin. Immunol. 2008, 20, 86−100.
Brittain HG. Polymorphism in Pharmaceutical Solids. First Edition. Informa Healthcare. New York: Marcel Dekker Inc; 1999.
Press W, Flannery BP, Tenkolsky S, Vetterling WT. Preparation and Characterization of ranitidine hydrochloride crystals. 2nd ed. Numerical Recipes. England: Cambridge University Press; 1986.
Laurance. L, Brunton JS, Keith LP. Goodman and Gilman’s The Pharmacological Basis of Therapeutics – 11th ed., Published by McGrawhill – Medical Publishing Division, 2006:892.
Charles. Dev. Pharmacol. Ther.,1993, 20(3–4), 205–210.
Wells IJ. Pharmaceutical Preformulation: The Physicochemical properties of Drug Substances. 1st ed. Chichester: Ellis Horwood Ltd, Halsted Press; 1988.
Haleblium JK. Characterization of Habits and Crystalline Modification of Solids and their Pharmaceutical Applications. J.Pharm. Sci. 1975; 64(8):1269-88.
Brittain HG. Polymorphism in Pharmaceutical Solids. First Edition. Informa Healthcare. New York: Marcel Dekker Inc; 1999.
Subrahmanyam CV. Essentials of Physical Pharmacy. First Edition. New Delhi: Vallabh Prakashan; 2003.
Banerjee S, Bandyopadhyay A, Bhattacharjee R, Mukherjee A, Halder A. Serum levels of chloramphenicol in children, rhesus, monkeys, and cats after administration of chloramphenicol palmitate suspension. J Pharm Sci. 1971; 60:153-5.
Shinbyoung AH, Fang G, Kariuki BM, Harris KDM. Abundant Polymorphism in a system with multiple hydrogen bonding opportunities: Oxalyldihydrazide. J Am Chem Soc. 2006; 128:8441-52.
Evans G. A Handbook of Bio analysis and drug metabolism. First Edition. US: CRC Press; 2004.
Mullin, J.W. In Crystallisation, 3rd Ed.; Butterworths: Oxford, UK, 1993.
Huttenrauch, R. Modification of Starting Materials to Improve Tableting Properties. Pharm. Ind. 1983, 4, 435–440.
York, P. Solid-State Properties of Powders in the Formulation and Processing of Solid Dosage Forms. Int. J. Pharm. 1983, 14, 1–28.
Marshall, P.V.; York, P. The Compaction Properties of Nitrofurantoin Samples Crystallised from Different Solvents. Int. J. Pharm. 1991, 67, 59–65.
Garekani, H.A.; Ford, J.L.; Rubinstein, M.H.; Rajabi-Siahboomi, A.R. Formation and Compression Properties of Prismatic Polyhedral and Thin Plate-like Crystals of Paracetamol. Int. J. Pharm. 1999, 187, 77–89.
Gonda, I.; Abd-El Khalik, A.F.; Britten, A.Z. Solid Forms of Hexamethylmelamine. J. Pharm. Pharmacol. 1985, 37, 117P.
Marshall, P.V.; York, P. Crystallisation Solvent Induced Solid-State and Particulate Modifications of Nitrofurantoin. Int. J. Pharm. 1989, 55, 257–263.
Khan, G. M.; Jiabi, Z. Preparation, Characterization, and Evaluation of Physicochemical Properties of Different Crystalline Forms of Ibuprofen. Drug Dev. Ind. Pharm. 1998, 24 (5), 463–471.
Rasenack, N.; Müller, B. W. Properties of Ibuprofen Crystallized Under Various Conditions: A Comparative Study. Drug Dev. Ind. Pharm. 2002, 28 (9), 1077–1089. 10. Hammouda, Y. E.; El-Khordagui, L. K.; Darwish, I. A.; El-Kamel, A. H. Manipulation of Powder Characteristics by Interactions at the Solid–Liquid Interface: 1-Sulphadiazine. Eur. J. Pharm. Sci. 1999, 8, 283.
Tiwary, A. K. Modification of Crystal Habit and Its Role in Dosage Form Performance. Drug Dev. Ind. Pharm. 2001, 27 (7), 699–709.
Lee, T.; Kuo, C. S.; Chen, Y. H. Solubility, Polymorphism, Crystallinity, and Crystal Habit of Acetaminophen and Ibuprofen by Initial Solvent Screening. Pharm. Technol. 2006, 30 (10), 72–92.
Antonio SG, Benini FR, Furlan FF, Rosa PCP, Paiva-Santos CO, Quantitative Phase Analyses Through The Rietveld Method withXRay Powder Diffraction Data of Heat-Treated CarbamazepineForm III, J. Pharm.Sci. 2011, July 100(7): 2658–2664.
Brittain HG, Methods for the characterization of polymorphs and solvates. In HG Brittain (ed.) Polymorphism in Pharmaceutical Solids. Marcel Dekker, Inc., New York, 1999, 227-278.
FDA, Guidance for industry, ANDAs: Pharmaceutical solid polymorphism. Chemistry, manufacturing and controls information. U.S Department of helth and human services food and drug administration. Center for drug evaluation and research (CDER), 2007.
Grant DJ, In HG Brittain (ed.) Polymorphism in Pharmaceutical Solids. Marcel Dekker, Inc., New York, 1-31, 1999.
Chang DF, Wong V. Two clinical trials of an intraocular steroid delivery system for cataract surgery. Trans Am Ophthal Soc 1999;97:261–74.
Tan DT, Chee SP, Lim L, Lim AS. Randomized clinical trial of a new dexamethasone delivery system (Surodex) for treatment of post-cataract surgery inflammation. Ophthalmology. 1999;106(2):223–31.
Kodama M, Numaga J, Yoshida A, Kaburaki T, Oshika T, Fujino Y, et al. Effects of new dexamethasone-delivery system (Surodex) on experimental intraocular inflammation models. Graefes Arch Clinical Exp Ophthal 2003;241(11):927–33.
Kagaya F, Usui T, Kamiya K, Ishii Y, Tanaka S, Amano S, et al. Intraocular dexamethasone delivery system for corneal transplantation in an animal model. Cornea 2002;21(2):200–2.
Nakase H, Okazaki K, Tabata Y, Uose S, Ohana M, Uchida M. Development of an oral drug delivery system targeting immune-regulating cells in experimental inflammatory bowel disease: a new therapeutic strategy. J Pharmacol Exp Therapeutics. 2000;292(1):15–21.
Leopold CS, Eikeler D. Basic coating polymers for the colonspecific drug delivery in inflammatory bowel disease. Drug Devel Ind Pharm 2000;26912:1239–46.
Nakase H, Okazaki K, Tabata Y, Chiba T. Biodegradable microspheres targeting mucosal immune-regulating cells: new approach for treatment of inflammatory bowel disease. J Gastroent 2003;38:59–62.
Nakase H, Okazaki K, Tabata Y, Uosa S, Ohana M, Uchda K. An oral drug delivery system targeting immune-regulating cells ameliorates mucosal injury in trinitrobenzene sulfonic acidinduced colitis. J Pharmacol Exp Therapeutics 2001;297(3): 1122–8.
Okazaki K, Nakase H, Watanabe N, Tabata Y, Ikada Y, Chiba T. Intestinal drug delivery systems with biodegradable microspheres targeting mucosal immune-regulating cells for chronic inflammatory colitis. J Gastroent 2002;37:44–52.
Dev V, Eigler N, Fishbein MC, Tian Y, Hickey A, Rechavia E. Sustained local drug delivery to the arterial wall via bioresorbable microspheres. Catheter Cardiovasc Diag 1997;41(3):324–32.
Guzman LA, Labhasetwar V, Song C, Jang Y, Linkoff AM, Levy R. Local intraluminal infusion of biodegradable polymeric nanoparticles. A novel approach for prolonged drug delivery after balloon angioplasty. Circulation 1996;94(6):1441–8.
Lincoff AM, Furst JG, Ellis SG, Tuch RJ, Topol EJ. Sustained local delivery of dexamethasone by novel intravascular eluting stent to prevent restenosis in the porcine coronary injury model. J Am Coll Cardiol 1997;29(4):806–16.
Hendel J, Brodthages H. Entero-Hepatic cycling of methotrexate estimate by use of D-isomer as reference marker. Eur J Clin Pharmacol 1984; 26: 103-7.
Bort R, Ponsoda X, Carrasco E, Gomez-Lechon MJ, Castell JV. Metabolism of Aceclofenac in humans, American Society for Pharmacology and Experimental Therapeutics. 1996; 24(8):834- 41.
Binoy JP. Rheumatoid arthritis- A Therapeutic review. Calicut Medical Journal 2004; 2: 2-6.
Shivakumar HG. Influence of solvents on crystal habit and properties of paracetamol crystals. Ind J Pharm Sci 1999;61(2):100-4.
Turghun M, Jide W, Mei L, Jian C. Monitoring Dissolution Rate of Amiodarone Tablets by a Multiple Fiber-Optic Sensor System. Dissolution Technologies 2008:22-27.
Gibaldi M, Feldman S. Establishment of sink conditions in dissolution rate determinations - theoretical considerations and application to non-disintegrating dosage forms. J Pharm Sci 1967; 56:1238–1242.
Costa P, Jose Manuel Sousa L.Modeling and comparison of dissolution profiles. Eur J Pharm Sci 2001; 13:123–33.
Mutalik S, Usha AN, Reddy MS, Ranjith AK, Pandey S. Improved bioavailability of aceclofenac from spherical agglomerates: development, in vitro and preclinical studies. Pak J Pharm Sci 2007; 3:218–226.
Mutalik S, Naha A, Usha N, Ranjith K, Musmade P, Manoj K, Anju P, Prasanna S. Preparation, In vitro, preclinical and clinical evaluations of once daily sustained release tablets of aceclofenac. Arch Pharm Res 2007; 30:222–234.
Smikalla MM, Urbanetz NA. The influence of povidone K17 on the storage stability of solid dispersions of nimodipine and polyethylene glycol 2007; 66:106–112.
Vitez I. Utilization of DSC for Pharmaceutical crystal form quantitation. J Therm Anal Calorim 2004; 78(1):33-45.
Hamzah MM, Mohammad HS, Abdulatif AA. In Vitro Dissolution Kinetic Study of Theophylline from Hydrophilic and Hydrophobic Matrices. Acta Poloniae Pharmaceutica and Drug Research 2006; 63(1):63-67.
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