Co-crystallization of sofosbuvir with sugars for enhanced dissolution rate

  • Taher Mohamed Yassen Mousa department of pharmaceutical technology, faculty of pharmacy, menofia university
  • Donia AA department of pharmaceutical technology, faculty of pharmacy, menofia university.
  • El Maghraby GM department of pharmaceutical technology, faculty of pharmacy, Tanta university.
Keywords: Sofosbuvir co-crystals; Hydrophilic sugars; Wet co-grinding method; Dissolution efficiency; Powder X-ray diffraction pattern

Abstract

Sofosbuvir is one of the direct acting antiviral agents which is approved in the treatment of chronic HCV in combination with other agents. The low aqueous solubility of sofosbuvir resulted in slow dissolution which is supposed to be responsible for its low and variable bioavailability after oral administration. Accordingly, the objective of this work was to investigate the effect of co-crystallization of sofosbuvir with hydrophilic sugars on its crystalline structure and dissolution rate. Mixtures of sofosbuvir with hydrophilic sugars at various molar ratios were prepared by ethanol assisted kneading followed by drying. The dry products were then characterized by attenuated total reflectance fourier transform infrared spectroscopy (ATR FTIR), differential scanning calorimetry (DSC), powder X-ray diffraction (XRD) and in vitro dissolution studies. Combined instrumental analysis reflected development of new crystalline species of co-crystal type. This was evidenced by the existence of hydrogen bonding as shown from FTIR spectra, change in the thermal behaviour and appearance of new diffraction peaks in the diffractograms recorded by XRD. The co-crystallization was associated by weakening of intermolecular bonds which resulted in significant increase in the dissolution rate of sofosbuvir. The study introduced hydrophilic sugars as co-crystal co-formers for enhanced dissolution of sofosbuvir.

References

Apshingekar, P. P., Aher, S., Kelly, A. L., Brown, E. C., & Paradkar, A. (2017). Synthesis of caffeine/maleic acid co-crystal by ultrasound-assisted slurry co-crystallization. Journal of pharmaceutical sciences, 106(1), 66-70.‏
‏‏‏ Arafa, M. F., El-Gizawy, S. A., Osman, M. A., & El Maghraby, G. M. (2016). Sucralose as co-crystal co-former for hydrochlorothiazide: development of oral disintegrating tablets. Drug Development and Industrial Pharmacy, 42(8), 1225-1233.‏.‏
Arafa, M. F., El-Gizawy, S. A., Osman, M. A., & El Maghraby, G. M. (2017). Co-crystallization for enhanced dissolution rate of nateglinide: In vitro and in vivo evaluation. Journal of Drug Delivery Science and Technology, 38, 9-17.‏.
Arafa, M. F., El-Gizawy, S. A., Osman, M. A., & El Maghraby, G. M. (2018). Xylitol as a potential co-crystal co-former for enhancing dissolution rate of felodipine: preparation and evaluation of sublingual tablets. Pharmaceutical development and technology, 23(5), 454-463.‏
Chakravarthy, V. A., Sailaja, B., & Praveen Kumar, A. (2016). Method development and validation of ultraviolet-visible spectroscopic method for the estimation of hepatitis-c drugs-daclatasvir and sofosbuvir in active pharmaceutical ingredient form. Asian. J. Pharm. Clin. Res, 9, 61-66.‏
Bak, A., Gore, A., Yanez, E., Stanton, M., Tufekcic, S., Syed, R., ... & Koparkar, A. (2008). The co‐crystal approach to improve the exposure of a water‐insoluble compound: AMG 517 sorbic acid co‐crystal characterization and pharmacokinetics. Journal of pharmaceutical sciences, 97(9), 3942-3956.‏
‏ Berden, F. A. C., Kievit, W., Baak, L. C., Bakker, C. M., Beuers, U., Boucher, C. A. B., ... & Drenth, J. P. H. (2014). Dutch guidance for the treatment of chronic hepatitis C virus infection in a new therapeutic era. Netherlands Journal of Medicine, 72(8), 388-400.
Boksa, K., Otte, A., & Pinal, R. (2014). Matrix-assisted cocrystallization (MAC) simultaneous production and formulation of pharmaceutical cocrystals by hot-melt extrusion. Journal of pharmaceutical sciences, 103(9), 2904-2910.‏
Bouchal, F., Skiba, M., Chaffai, N., Hallouard, F., Fatmi, S., & Lahiani-Skiba, M. (2015). Fast dissolving cyclodextrin complex of piroxicam in solid dispersion Part I: Influence of β-CD and HPβ-CD on the dissolution rate of piroxicam. International Journal of Pharmaceutics, 478(2), 625-632.‏
‏ Brizuela, A. B., Raschi, A. B., Castillo, M. V., Leyton, P., Romano, E., & Brandán, S. A. (2013). Theoretical structural and vibrational properties of the artificial sweetener sucralose. Computational and Theoretical Chemistry, 1008, 52-60.‏
Charlton, M., Everson, G. T., Flamm, S. L., Kumar, P., Landis, C., Brown Jr, R. S., ... & Romero-Marrero, C. (2015). Ledipasvir and sofosbuvir plus ribavirin for treatment of HCV infection in patients with advanced liver disease. Gastroenterology, 149(3), 649-659.‏
‏ Choi, J. S., & Park, J. S. (2017). Design of PVP/VA S-630 based tadalafil solid dispersion to enhance the dissolution rate. European journal of pharmaceutical sciences, 97, 269-276.‏
Chun, N. H., Wang, I. C., Lee, M. J., Jung, Y. T., Lee, S., Kim, W. S., & Choi, G. J. (2013). Characteristics of indomethacin–saccharin (IMC–SAC) co-crystals prepared by an anti-solvent crystallization process. European Journal of Pharmaceutics and Biopharmaceutics, 85(3), 854-861.‏
Cysewski, P., & Przybyłek, M. (2017). Selection of effective cocrystals former for dissolution rate improvement of active pharmaceutical ingredients based on lipoaffinity index. European Journal of Pharmaceutical Sciences, 107, 87-96.‏
Dizaj, S. M., Mennati, A., Jafari, S., Khezri, K., & Adibkia, K. (2015). Antimicrobial activity of carbon-based nanoparticles. Advanced pharmaceutical bulletin, 5(1), 19.‏.‏
Essa, E. A., Elbasuony, A. R., Abdelaziz, A. E., & El Maghraby, G. M. (2019). Co-crystallization for enhanced dissolution rate of bicalutamide: preparation and evaluation of rapidly disintegrating tablets. Drug Development and Industrial Pharmacy.‏
‏ He, G., Jacob, C., Guo, L., Chow, P. S., & Tan, R. B. (2008). Screening for cocrystallization tendency: the role of intermolecular interactions. The Journal of Physical Chemistry B, 112(32), 9890-9895.‏
‏ Hu, L., Yang, J., Liu, W., & Li, L. (2011). Preparation and evaluation of ibuprofen-loaded microemulsion for improvement of oral bioavailability. Drug Delivery, 18(1), 90-95.‏
Islam, M. A., Alam, M. M., Sikdar, K. Y. K., Al Hossain, A. M., & Rouf, A. S. S. (2021). Development and Characterization of a Combination Tablet Dosage Form Containing Sofosbuvir and Ribavirin Using Design of Experiments (DoE) Approach. Dhaka University Journal of Pharmaceutical Sciences, 20(1), 121-133.‏
Jaafar, I. S., & Radhi, A. A. (2020). Preparation and physicochemical characterization of cocrystals for enhancing the dissolution rate of glimepiride. Journal of Advanced Pharmacy Education & Research| Jul-Sep, 10(3), 69.‏
Jaipal, A., Pandey, M. M., Charde, S. Y., Raut, P. P., Prasanth, K. V., & Prasad, R. G. (2015). Effect of HPMC and mannitol on drug release and bioadhesion behavior of buccal discs of buspirone hydrochloride: In-vitro and in-vivo pharmacokinetic studies. Saudi Pharmaceutical Journal, 23(3), 315-326.‏
Jones, W., Motherwell, W. S., & Trask, A. V. (2006). Pharmaceutical cocrystals: An emerging approach to physical property enhancement. MRS bulletin, 31(11), 875-879.‏.‏
‏ Kang, J. H., Oh, D. H., Oh, Y. K., Yong, C. S., & Choi, H. G. (2012). Effects of solid carriers on the crystalline properties, dissolution and bioavailability of flurbiprofen in solid self-nanoemulsifying drug delivery system (solid SNEDDS). European journal of pharmaceutics and biopharmaceutics, 80(2), 289-297.
‏ Kassem, F. A., Abdelaziz, A. E., & El Maghraby, G. M. (2021). Ethanol-assisted kneading of apigenin with arginine for enhanced dissolution rate of apigenin: development of rapidly disintegrating tablets. Pharmaceutical Development and Technology, 26(6), 693-700.‏
‏ Khadka, P., Ro, J., Kim, H., Kim, I., Kim, J. T., Kim, H., ... & Lee, J. (2014). Pharmaceutical particle technologies: An approach to improve drug solubility, dissolution and bioavailability. Asian journal of pharmaceutical sciences, 9(6), 304-316.‏
Khan, K. A. (1975). The concept of dissolution efficiency. Journal of pharmacy and pharmacology, 27(1), 48-49.‏
Lankalapalli, S., Sandela, D., Pudi, A., & Kolluru, N. (2017). Preparation and evaluation of sofosbuvir polyelectrolyte microparticles. International journal of Research in pharmacy and Chemistry, 7(4), 547-557.‏.
Mehmood, Y., Khan, I. U., Shahzad, Y., Khan, R. U., Khalid, S. H., Yousaf, A. M., ... & Shah, S. U. (2020). Amino-decorated mesoporous silica nanoparticles for controlled sofosbuvir delivery. European journal of pharmaceutical sciences, 143, 105184.‏184.
Moretti, M. D. L., Gavini, E., Juliano, C., Pirisino, G., & Giunchedi, P. (2001). Spray-dried microspheres containing ketoprofen formulated into capsules and tablets. Journal of microencapsulation, 18(1), 111-121.‏
Ochi, M., Inoue, R., Yamauchi, Y., Yamada, S., & Onoue, S. (2013). Development of meloxicam salts with improved dissolution and pharmacokinetic behaviors in rats with impaired gastric motility. Pharmaceutical research, 30(2), 377-386.‏
Ochi, M., Kawachi, T., Toita, E., Hashimoto, I., Yuminoki, K., Onoue, S., & Hashimoto, N. (2014). Development of nanocrystal formulation of meloxicam with improved dissolution and pharmacokinetic behaviors. International journal of pharmaceutics, 474(1-2), 151-156.‏
Padrela, L., Rodrigues, M. A., Velaga, S. P., Fernandes, A. C., Matos, H. A., & de Azevedo, E. G. (2010). Screening for pharmaceutical cocrystals using the supercritical fluid enhanced atomization process. The Journal of Supercritical Fluids, 53(1-3), 156-164.‏
‏ Pêcego, I. G. (2018). Synthesis of glibenclamide cocrystals through grinding methods (Doctoral dissertation).‏
‏ Rajbanshi, K., Bajracharya, R., Shrestha, A., & Thapa, P. (2014). Dissolution enhancement of aceclofenac tablet by solid dispersion technique. International Journal of Pharma Sciences and Research, 5(4), 127-139.‏
Rawat, S., & Jain, S. K. (2004). Solubility enhancement of celecoxib using β-cyclodextrin inclusion complexes. European journal of pharmaceutics and biopharmaceutics, 57(2), 263-267.‏‏‏‏‏
‏ Reis, C. P., Ferreira, J. P., Candeias, S., Fernandes, C., Martinho, N., Aniceto, N., ... & Figueiredo, I. V. (2014). Ibuprofen nanoparticles for oral delivery: proof of concept. Journal of Nanomedicine & Biotherapeutic Discovery, 4(1), 1.‏
Samprasit, W., Akkaramongkolporn, P., Kaomongkolgit, R., & Opanasopit, P. (2018). Cyclodextrin-based oral dissolving films formulation of taste-masked meloxicam. Pharmaceutical Development and Technology, 23(5), 530-539.‏
Sironi, D., Rosenberg, J., Bauer-Brandl, A., & Brandl, M. (2017). Dynamic dissolution-/permeation-testing of nano-and microparticle formulations of fenofibrate. European Journal of Pharmaceutical Sciences, 96, 20-27.‏
Sopyan, I., Fudholi, A., Muchtaridi, M., & Sari, I. P. (2017). Simvastatin-nicotinamide co-crystal: design, preparation and preliminary characterization. Tropical Journal of Pharmaceutical Research, 16(2), 297-303.‏
Turker, M. (2013). FDA Approves ‘Game Changer’Hepatitis-C Drug Sofosbuvir. Medscape. 6th December..‏
Velaga, S. P., Basavoju, S., & Boström, D. (2008). Norfloxacin saccharinate–saccharin dihydrate cocrystal–A new pharmaceutical cocrystal with an organic counter ion. Journal of Molecular Structure, 889(1-3), 150-153.‏
Viertelhaus, M., & Hafner, A. (2015). Co-crystals and their advantages for APIs with challenging properties. CHIMICA OGGI-CHEMISTRY TODAY, 33(5), 23-26.‏
Wang, I. C., Lee, M. J., Sim, S. J., Kim, W. S., Chun, N. H., & Choi, G. J. (2013). Anti-solvent co-crystallization of carbamazepine and saccharin. International journal of pharmaceutics, 450(1-2), 311-322.‏
Xing, Q., Song, J., You, X., Xu, D., Wang, K., Song, J., ... & Hu, H. (2016). Microemulsions containing long-chain oil ethyl oleate improve the oral bioavailability of piroxicam by increasing drug solubility and lymphatic transportation simultaneously. International journal of pharmaceutics, 511(2), 709-718.‏
Ziaee, A., Albadarin, A. B., Padrela, L., Faucher, A., O'Reilly, E., & Walker, G. (2017). Spray drying ternary amorphous solid dispersions of ibuprofen–An investigation into critical formulation and processing parameters. European Journal of Pharmaceutics and Biopharmaceutics, 120, 43-51.‏
Published
2023-02-01
How to Cite
Mousa, T. M. Y., Donia, A. A., & El Maghraby, G. M. (2023). Co-crystallization of sofosbuvir with sugars for enhanced dissolution rate. Indonesian Journal of Pharmacy, 34(1). https://doi.org/10.22146/ijp.5452
Section
Research Article