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A new soluble and bioactive polymorph of praziquantel

Zanolla, Debora and Perissutti, Beatrice and Passerini, Nadia and Chierotti, Michele R. and Hasa, Dritan and Voinovich, Dario and Gigli, Lara and Demitri, Nicola and Geremia, Silvano and Keiser, Jennifer and Cerreia Vioglio, Paolo and Albertini, Beatrice. (2018) A new soluble and bioactive polymorph of praziquantel. European Journal of Pharmaceutics and Biopharmaceutics, 127. pp. 19-28.

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Official URL: https://edoc.unibas.ch/64897/

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Abstract

Praziquantel is the only available drug to treat Schistosomiasis. However, its utilization is limited by many drawbacks, including the high therapeutic dose needed, resulting in large tablets and capsules difficult to be swallowed, especially from pediatric patients. In this study, an alternative option to overcome these disadvantages is proposed: to switch to a novel crystalline polymorph of racemic compound praziquantel. The preparation of the crystalline polymorph was realized via a neat grinding process in a vibrational mill. The new phase (Form B) was chemically identical to the starting material (as proved by HPLC,; 1; H NMR, and polarimetry), but showed different physical properties (as evaluated by SEM, differential scanning calorimetry, thermogravimetry, ATR-FTIR spectroscopy, X-ray powder diffraction, and solid-state NMR). Furthermore, the crystal structure of the new phase was solved from the powder synchrotron X-ray diffraction pattern, resulting in a monoclinic C2/c cell and validated by DFT-D calculation. Moreover the simulated solid-state NMR; 13; C chemical shifts were in excellent agreement with the experimental data. The conversion of original praziquantel into Form B showed to affect positively the water solubility and the intrinsic dissolution rate of praziquantel. Both the in vitro and in vivo activity against Schistosoma mansoni were maintained. Our findings suggest that the new phase, that proved to be physically stable for at least one year, is a promising product for designing a new praziquantel formulation.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology > Helminth Drug Development (Keiser)
UniBasel Contributors:Keiser, Jennifer
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Elsevier
ISSN:0939-6411
e-ISSN:1873-3441
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:04 Jul 2018 08:58
Deposited On:04 Jul 2018 08:58

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