Pre-formulation solubility study of praziquantel in different media and solubilizing agents using the saturation shake-flask method
Rokaya O. Amara, Nesrein M. Bendala
Abstract
Praziquantel is a medication used to treat schistosomiasis. It has low bioavailability due to poor solubility in water and common solvents, resulting in its availability only in a solid dosage form. This study is aimed to enhance the solubility of praziquantel by the use of various solubilizing agents. The solubility evaluation was conducted using the shake-flask method. The solvents were; buffered phosphate pH 7.4, 0.5% propylene glycol in buffered phosphate pH 7.4, 0.2% tween 80 in buffered phosphate pH 7.4, 30% methanol in buffered phosphate pH 7.4, and assessment of the solubility of the drug in 0.1 N hydrochloric acid, 0.2% sodium lauryl sulfate, and a mixture of 0.2% sodium lauryl sulfate in 0.1 N hydrochloric acid. The solubility of praziquantel was determined at a temperature of 37±2°C, and the concentrations were detected by high-performance liquid chromatography at λ=210 nm. The results show that the solubility of praziquantel was 124.3±2 µg/ml in 30.0% methanol in buffered phosphate pH 7.4, 100.6±2 µg/ml in 0.2% tween 80 in buffered phosphate pH 7.4, 112.4 µg/ml in 0.1 N hydrochloric acid, 370.29 µg/ml in 0.2% sodium lauryl sulfate, and 278.7 µg/ml in a mixture of 0.2% sodium lauryl sulfate in 0.1 N hydrochloric acid (pH 2). Thus, praziquantel can be considered a highly soluble drug in 0.2% sodium lauryl sulfate. Other surfactants may improve the solubility of such poorly soluble drugs.
Keywords
References
- Vale N, Gouveia MJ, Rinaldi G, Brindley PJ, Gärtner F, Correia da Costa JM (2017) Praziquantel for Schistosomiasis: single-drug metabolism revisited, mode of action, and resistance. Antimicrobial Agents and Chemotherapy. 61 (5): e02582-16. doi: 10.1128/AAC.02582-16
- World Health Organization (2023) WHO model list of essential medicines, 23rd list, 67 pages. WHO reference number: WHO/MHP/HPS/EML/2023.02
- Caffrey CR (2007) Chemotherapy of schistosomiasis: present and future. Current Opinion in Chemical Biology. 11 (4): 433-439. doi: 10.1016/j.cbpa.2007.05.031
- El-Lakkany N, Seif el-Din SH, Heikal L (2012) Bioavailability and in-vivo efficacy of a praziquantel-polyvinyl pyrrolidone solid dispersion in Schistosoma mansoni-infected mice. European Journal of Drug Metabolism and Pharmacokinetics. 37 (4): 289-299. doi: 10.1007/s13318-012-0089-6
- Chaud MV, Lima AC, Vila MM, Paganelli MO, Paula FC, Pedreiro LN, Gremiao MPD (2013) Development and evaluation of praziquantel solid dispersions in sodium starch glycolate. Tropical Journal of Pharmaceutical Research. 12 (2): 163-168. doi: 10.4314/tjpr.v12i2.5
- Cugovˇcan M, Jablan J, Lovri´c J, Cinˇci´c D, Gali´c N, Jug M (2017) Biopharmaceutical characterization of praziquantel cocrystals and cyclodextrin complexes prepared by grinding. Journal of Pharmaceutics and Biomedical Analysis. 137: 42-53. doi: 10.1016/j.jpba.2017.01.025
- Rodrigues SG, Chaves IS, Melo NFS, Jesus MB, Fraceto LF, Fernandes SA, Paula E, de Freitas MP, Pinto LDMA, (2010) Computational analysis and physico-chemical characterization of an inclusion compound between praziquantel and methyl-cyclodextrin for use as an alternative in the treatment of Schistosomiasis. Journal of Inclusion Phenomena and Macrocyclic Chemistry. 70 (1-2): 19-28. doi: 10.1007/s10847-010-9852-y
- Maragos S, Archontaki H, Macheras P, Valsami G (2009) Effect of cyclodextrin complexation on the aqueous solubility and solubility/dose ratio of praziquantel. AAPS PharmSciTech. 10 (4): 1444-1451. doi: 10.1208/s12249-009-9346-7
- Arrúa EC, João M, Ferreira G, Salomon CJ, Nunes TG (2015) Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy. International Journal of Pharmaceutics. 496 (2): 812-821. doi: 10.1016/j.ijpharm.2015.11.026
- de Jesus MB, de Matos Alves Pinto L, Fraceto LF, Takahata Y, Lino ACS, Jaime C, de Paula E (2006) Theoretical and experimental study of a praziquantel and cyclodextrin inclusion complex using molecular mechanic calculations and 1H-nuclear magnetic resonance. Journal of Pharmaceutical and Biomedical Analysis. 41 (4): 1428-1432. doi: 10.1016/j.jpba.2006.03.010
- da Silva Mourão LC, Ribeiro Batista DRM, Honorato SB, Ayala AP, de Alencar Morais W, Barbosa EG, Raffin FN, deLima e Moura TFA (2016) Effect of hydroxypropyl methylcellulose on beta-cyclodextrin complexation of praziquantel in solution and in solid state. Journal of Inclusion Phenomena and Macrocyclic Chemistry. 85 (1-2): 151-160. doi: 10.1007/s10847-016-0614-3
- Mourão SC, Costa PI, Salgado HRN, Gremião MPD (2005) Improvement of antischistosomal activity of praziquantel by incorporation into phosphatidylcholine-containing liposomes. International Journal of Pharmaceutics. 295 (1-2): 157-162. doi: 10.1016/j.ijpharm.2005.02.009
- Partridge GJ, Rao S, Woolley LD, Pilmer L, Lymbery AJ, Prestidge CA (2019) Bioavailability and palatability of praziquantel incorporated into solid-lipid nanoparticles fed to yellowtail Kingfish Seriola lalandi. Comparative Biochemistry and Physiology. Toxicology and Pharmacology: CBP. 218: 14-20. doi: 10.1016/j.cbpc.2018.12.007
- Yang L, Geng Y, Li H, Zhang Y, You J, Chang Y (2009) Enhancement the oral bioavailability of praziquantel by incorporation into solid lipid nanoparticles. Pharmazie. 64 (2): 86-89. PMID: 19320279.
- Mainardes RM, Gremião MPD, Evangelista RC (2006) Thermo-analytical study of praziquantel-loaded PLGA nanoparticles. Revista Brasileira de Ciências Farmaceutics. 42 (4): 523-530. doi. 10.1590/S1516-93322006000 400007
- de Souza ALR, Andreani T, Nunes FM, Cassimiro DL, de Almeida AE, Ribeiro CA, Sarmento VHV, Gremião, MPD, Silva AM, Souto EB (2012) Loading of praziquantel in the crystal lattice of solid lipid nanoparticles. Journal of Thermal Analysis and Calorimetry. 108 (1): 353-360. doi: 10.1007/s10973-011-1871-4
- Trastullo R, Dolci LS, Passerini N, Albertini B (2015) Development of flexible and dispersible oral formulations containing praziquantel for potential Schistosomiasis treatment of pre-school age children. International Journal of Pharmaceutics. 495 (1): 536-550. doi: 10.1016/j.ijpharm.2015.09.019
- Amara RO, Ramadan AA, El-Moslemany RM, Eissa MM, El-Azzouni MZ, El-Khordagui LK (2018) Praziquantel-lipid nanocapsules: an oral nanotherapeutic with potential Schistosoma mansoni tegumental targeting. International Journal of Nanomedicine. 13: 4493-4505. doi: 10.2147/IJN.S167285
- McNaught AD, Wilkinson A (1997) Compendium of chemical technology (IUPAC Chemical data). 2nd ed., 464. Wiley, USA. ISBN: 978-0865426849.
- Taylor KMG, Aulton ME (2002) Pharmaceutics: The science of dosage form design, 2nd ed., Churchill Livingstone, London, UK. ISBN: 978-0443055171.
- Pokhrel DR, Sah MK, Gautam B, Basak HK, Bhattarai A, Chatterjee A (2023) A recent overview of surfactant-drug interactions and their importance. Royal Society of Chemistry Advances. 13: 17685-17704. doi: 10.1039/D3RA02883F
- Li M, Qiao N, Wang K (2013) Influence of sodium lauryl sulfate and tween 80 on carbamazepine-nicotinamide cocrystal solubility and dissolution behavior. Pharmaceutics. 5 (4): 508-524. doi: 10.3390/pharmaceutics5040508
- Long B, Li J, Zhang R, Wan L (2010) Solubility of benzoic acid in acetone, 2-propanol, acetic acid and cyclohexane: Experimental measurement and thermodynamic modeling. Fluid Phase Equilibria. 297 (1): 113-120. doi: 10.1016/ j.fluid.2010.06.021
- Ronco C, Bellomo R, Kellum J, Ricci Z (2019) Critical care nephrology. 1362-1411. 3rd ed., Elsevier, USA. ISBN: 9780323449427. doi: 10.1016/B978-0-323-44942-7.00229-6.
- Ray SD (2024) Side effects of drugs annual. 46: 1-590. 1st ed., Elsevier, USA. ISBN: 9780443294471.
- Mahapatra A, Patil V, Patil R (2020) Solubility enhancement of poorly soluble drugs by using novel techniques: A comprehensive review. International Journal of PharmTech Research. 13 (2): 80-93. doi: 10.20902/IJPTR.2019. 130211
- Chaurasia G (2016) A review on pharmaceutical preformulation studies in formulation and development of new drug molecules. International Journal of Pharmaceutical Sciences and Research. 7 (6): 2313-2320. doi: 10.13040/ IJPSR.0975-8232.7(6).2313-20
- Glomme A, März J, Dressman JB (2005) Comparison of a miniaturized shake-flask solubility method with automated potenciometric acid/base titrations and calculated solubilities. Journal of Pharmaceutical Sciences. 94 (1): 1-16. doi: 10.1002/jps.20212
- Benet LZ, Broccatelli F, Oprea TI (2011) BDDCS applied to over 900 drugs. The AAPS Journal. 13 (4): 519-547. doi: 10.1208/s12248-011-9290-9
- Persson LC, Porter CJH, Charman WN, Bergström CAS (2013) Computational prediction of drug solubility in lipid-based formulation excipients. Pharmaceutical Research. 30 (12): 3225-3237. doi: 10.1007/s11095-013-1083-7
- El-Subbagh HI, Al-Badr AA (1998) Praziquantel. Analytical Profiles of Drug Substances and Excipients. 25: 463-500. doi: 10.1016/S0099-5428(08)60760-1
- Chen L, Wesley J, Bhattachar S, Ruiz B, Bahash K, Babu S (2003) Dissolution behavior of a poorly water-soluble compound in the presence of tween 80. Pharmaceutical Research. 20: 797-801. doi: 10.1023/A:1023493821302
- Hosseini SZ, Bozorgmehr MR, Masrurnia M, Beyramabadi SA (2018) Study of the effects of methanol, ethanol and propanol alcohols as Co-solvents on the interaction of methimazole, propranolol and phenazopyridine with carbon dioxide in supercritical conditions by molecular dynamics. The Journal of Supercritical Fluids. 140: 91-100. doi: 10.1016/j.supflu.2018.06.005
- Zhou R, Li S (2009) Supercritical carbon dioxide and co-solvent extractions of estradiol and progesterone from antler velvet. Journal of Food Composition and Analysis. 22 (1): 72-78. doi: 10.1016/j.jfca.2008.07.008
Submitted date:
11/11/2024
Reviewed date:
12/27/2024
Accepted date:
01/12/2025
Publication date:
01/20/2025