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Article

New Pharmaceutical Salts of Trazodone

1
Institute of Organic Chemistry and Technology, Faculty of Chemical and Engineering and Technology, Cracow University of Technology, 24 Warszawska Street, 31-155 Cracow, Poland
2
Department of Analytical Chemistry and Biomaterials, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-093 Warsaw, Poland
3
Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
4
Zbigniew Majka Consulting, ul Górczewska 200c /58, 01-460 Warszawa, Poland
*
Authors to whom correspondence should be addressed.
Academic Editor: Pradip K. Bhowmik
Molecules 2021, 26(3), 769; https://doi.org/10.3390/molecules26030769
Received: 23 December 2020 / Revised: 20 January 2021 / Accepted: 26 January 2021 / Published: 2 February 2021
(This article belongs to the Section Medicinal Chemistry)
New pharmaceutically acceptable salts of trazodone (trazodone hydrogen bromide and trazodone 1-hydroxy-2-naphthonic acid) for the treatment of central nervous system disorders are synthesized and described. Although trazodone salts are poorly crystalline, single-crystal X-ray diffraction data for trazodone 1-hydroxy-2-naphthonic acid were collected and analyzed as well as compared to the previously described crystal structure of commercially available trazodone hydrochloride. The powder samples of all new salts were characterized by Fourier transform infrared spectroscopy, X-ray diffraction and 13C solid-state nuclear magnetic resonance spectroscopy. Spectroscopic studies were supported by gauge including projector augmented wave (GIPAW) calculations of carbon chemical shielding constants. The main goal of our research was to find salts with better physicochemical properties and to make an attempt to associate them with both the anion structure and the most prominent interactions exhibited by the protonated trazodone cation. The dissolution profiles of trazodone from tablets prepared from various salts with lactose monohydrate were investigated. The studies revealed that salts with simple anions show a fast release of the drug while the presence of more complex anion, more strongly interacting with the cation, effects a slow-release profile of the active substance and can be used for the preparation of the tables with a delay or prolonged mode of action. View Full-Text
Keywords: trazodone; drug design; dissolution; crystal structure; solid-state NMR (SSNMR) spectroscopy; GIPAW calculation trazodone; drug design; dissolution; crystal structure; solid-state NMR (SSNMR) spectroscopy; GIPAW calculation
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MDPI and ACS Style

Jaśkowska, J.; Zaręba, P.; Drabczyk, A.; Kozak, A.; Madura, I.D.; Majka, Z.; Pindelska, E. New Pharmaceutical Salts of Trazodone. Molecules 2021, 26, 769. https://doi.org/10.3390/molecules26030769

AMA Style

Jaśkowska J, Zaręba P, Drabczyk A, Kozak A, Madura ID, Majka Z, Pindelska E. New Pharmaceutical Salts of Trazodone. Molecules. 2021; 26(3):769. https://doi.org/10.3390/molecules26030769

Chicago/Turabian Style

Jaśkowska, Jolanta, Przemysław Zaręba, Anna Drabczyk, Agnieszka Kozak, Izabela D. Madura, Zbigniew Majka, and Edyta Pindelska. 2021. "New Pharmaceutical Salts of Trazodone" Molecules 26, no. 3: 769. https://doi.org/10.3390/molecules26030769

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