Commenced in January 2007
Frequency: Monthly
Edition: International
Paper Count: 30517
Evaluation and Preparation of Crystal Modifications of Artesunate: In vivo Studies

Authors: S. Gupta, R. Chadha

Abstract:

Five crystal modifications of water insoluble artesunate were generated by recrystallizing it from various solvents with improved physicochemical properties. These generated crystal forms were characterized to select the most potent and soluble form. SEM of all the forms showed changes in external shape leading them to be different morphologically. DSC thermograms of Form III and Form V showed broad endotherm peaks at 83.04oC and 76.96oC prior to melting fusion of drug respectively. Calculated weight loss in TGA revealed that Form III and Form V are methanol and acetone solvates respectively. However, few additional peaks were appeared in XRPD pattern in these two solvate forms. All forms exhibit exothermic behavior in buffer and two solvates display maximum ease of molecular release from the lattice. Methanol and acetone solvates were found to be most soluble forms and exhibited higher antimalarial efficacy showing higher survival rate (83.3%) after 30 days.

Keywords: recrystallization, artesunate, Crystal modifications, in vivo studies

Digital Object Identifier (DOI): doi.org/10.5281/zenodo.1087472

Procedia APA BibTeX Chicago EndNote Harvard JSON MLA RIS XML ISO 690 PDF Downloads 2908

References:


[1] L. Borka., “Review on crystal polymorphism of substances, in the European pharmacoepiea,” Pharm Acta Helv., vol. 66, no.1, pp. 16–22, 1991.
[2] S. Mirza, I. Miroshnyk, J. Heinämäki, L. Christiansen, M. Karjalainen, and J. Yliruusi, “Influence of Solvents on the Variety of Crystalline Forms of Erythromycin,” AAPS PharmSci., vol. 5, no. 2, pp. 39–47, 2003.
[3] N. Rasenack, B. W. Muller, “Properties of Ibuprofen crystallized under various conditions: A comparative study” Drug Dev Ind Pharm.., vol. 28, no.9, pp. 278-289, 2002.
[4] F. Jamali, A. G. Mitchell, “The recrystallization and dissolution of acetylsalicylic acid,” Acta Pharm Suec.vol. 4, pp. 343-352, 1973.
[5] Jozwiakowski MJ, Nguyen NA, Sisco JM, Spancake CW. Solubility behavior of lamivudine crystal forms in recrystallization solvents. J Pharm Sci. 1996; 85(2): 193-199.
[6] Chemburkar SR, Bauer J, Deming K, Spiwek H, Patel K, Morris J, et al. Dealing with the impact of ritonavir polymorphs on the late stages of bulk drug process development. Org Process Res Dev. 2000; 4: 413-417.
[7] Byrn SR, Pfeiffer RR, Stowell JG. Solid-State Chemistry of Drugs, SSCI, West Lafayette, IN, 1999.
[8] Mohanachandran PS, Sindhumol PG, Kiran T. Enhancement of solubility and dissolution rate: an overview. International Journal of Comprehensive Pharmacy. Pharmacie Globale. 2010; 4 (11): 1-10.
[9] Javadzadeh Y, Hamedeyazdan S, Asnaashari S. Recrystallization of Drugs : Significance on Pharmaceutical Processing, Recrystallization, Prof. Krzysztof Sztwiertnia (Ed.), InTech, 2010; http://www.intechopen.com/books/recrystallization/recrystallizationofdrugs- significance-on-pharmaceutical-processing. ISBN: 978-953-51- 0122-2,
[10] Morris KR, Griesser UJ, Eckhardt CJ, Stowell JG. Theoretical approaches to physical transformations of active pharmaceutical ingredients during manufacturing processes. Adv Drug Deliv Rev. 2001; 48: 91–114.
[11] Khan GM, Jiabi Z. Preparation, characterization & evaluation of physicochemical properties of different crystalline forms of Ibuprofen. Drug Dev Ind Pharm. 1998; 24 (5):463 – 471.
[12] Yeo S, Kim M, Lee J. Recrystallization of sulfathiazole & chlorpropamide using supercritical fluid antisolvent process. The Journal of Supercritical Fluids. 2003; 25(2): 143-154.
[13] Urbanetz NA, Lippold BC. Solid Dispersion of nimodipne and polyoxyethene an additive prevents the drug from recrystalization.www.eurostar-science.org.
[14] Kawashima Y, Handa T, Takeuchi H, Okumura M, Katou H, Nagata O. Crystal modification of phenytoin with polyethylene glycol for improving mechanical strength, dissolution rate and bioavailability by a spherical crystallization technique. Chem Pharm Bull (Tokyo). 1986; 34(8): 3376-3383.
[15] Carino SR, Sperry DC, Hawley M. Relative bioavailability estimation of carbamazepine crystal forms using an artificial stomach-duodenum model. J Pharm Sci. 2006; 95(1):116-125.
[16] Sen D, Banerjee A, Ghosh AK, Chatterjee TK. Synthesis and antimalarial evaluation of some 4-quinazolinone derivatives based on febrifugine. Journal of Advanced Pharmaceutical Technology & Research. 2010; 1(4):401-405. DOI: 10.4103/0110-5558.76439
[17] Mohanraj V, Chen, Y. Nanoparticles-a review. Tropical Journal of Pharmaceutical Research. 2007; 5 (1): 561-573.
[18] Pan Y, Liu Y, Zeng G, Zhao L, Lai Z. Rapid synthesis of zeolitic imidazolate framework-8 (ZIF-8) nanocrystals in an aqueous system. Chem Commun (Camb). 2011; 47(7): 2071-3. doi: 10.1039/c0cc05002d.
[19] Cravillon J, Mu nzer S, Lohmeier SJ, Feldhoff A, Huber K, Wiebcke M. Rapid Room-Temperature Synthesis and Characterization of Nanocrystals of a Prototypical Zeolitic Imidazolate Framework. Chemistry of Materials. 2009; 21 (8): 1410-1412.
[20] Yellela SRK. Pharmaceutical technologies for enhancing oral bioavailability of poorly soluble drugs. Journal of Bioequivalence & Bioavailability. 2010; 2(2): 28–36.
[21] Kumar A, Sahoo SK, Padhee K, Kochar PS, Sathapathy A, Pathak N. Review on solubility enhancement techniques for hydrophobic drugs. Pharmacie Globale. 2011; 3(3): 001–007.
[22] Rinaki E, Valsami G, and Macheras P. Quantitative Biopharmacuetics Classification System; the central role of dose/solubility ratio. Pharm Res. 2003; 20: 1917.
[23] Chadha R, Kashid N, Jain DV. Characterization and quantification of amorphous content in some selected parenteral cephalosporins by calorimetric method. J Therm Anal Calorim. 2005; 81: 277-284.
[24] Chadha R, Kashid N, Jain DV. Microcalorimetric evaluation of the in vitro compatibility of amoxicillin/clavulanic acid and ampicillin/sulbatam with ciprofloxacin. J Pharm Biomed Anal. 2004; 36: 295-307.
[25] Giron D, Goldbronn C, Mutz M, Pfeffer S, Piechon P, Schwab P. Solid state characterization of pharmaceutical hydrates. J Therm Anal. 2002; 68:453–65. doi: 10.1023/A:1016031517430.
[26] Heng JY, Bismarck A, Williams DR. Anisotropic surface chemistry of crystalline pharmaceutical solids. AAPS PharmSciTech. 2006; 7(4): E12–E20.