Solid-state characterization of the new molecular salts of Pyridoxine

Cvetkovski, Aleksandar and Makreski, Petre and Stojanovska, Monika and Petrusevski, Gjorgji and Ugarkovic, Sonja and Pejov, Ljupco (2018) Solid-state characterization of the new molecular salts of Pyridoxine. In: 25th Conference of the SCS (Serbian Crystallography Society), 21-23 June 2018, Bajina Bašta, Serbija.

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Abstract

The concept of pharmaceutical salts, aimed to enhance the stability of acidic, basic or amphoteric drugs through their conversion by completed charge/proton transfer to one of the ionic form, that is electrostatically paired with counterion in form of salt type of API (Active Pharmaceutical Ingredients), has been accompained with subgroup of pharmaceutical cocrystals (PCC) [1]. The choice for the coformers (CF) for drug molecule is extened to wide range of substances that mutualy share the proton transfer ranging from neutral to charge-assisted H-bonds formation. The crystal structures of PCCs, formed by specific intermolecular motifs between API and CF are different from that of pure API and CF, and consequently influence to their diverse specific physical properties, i.e. API dissolution rate and solubility [2]; API pharmacokinetics [3] and bioavailability [4] in comparison with all solid forms in which API may exist [5]. In addition to previously determined structures on two molecular salts of API pyridoxine (vitamin B6, hereforth referred as PN), the β-hydroxypyridine derivative, with two aromatic acids, ferulic acid (FER) and syringic acid (SYR), that are potent antioxidants: PN-FER in 1:1, and PN-SYR hydrate in 1:1:1 molar ratio [6], we carried out their solidstate characterization. The pyridoxine cations are characterized by a O3-H…O2 intramolecular hydrogen bond, while the protonated nitrogen forms a strong N–H···O interaction with the coformer carboxylate group, whose short N···O distance is typical of charge-assisted hydrogen bonds. For the purpose of the work, we correlate the crystal structures in these PN molecular salts with their FT-IR and Raman spectra, as well as interpreted thermodynamic profiles fromthe TG/DSC measurements. [1] S. L. Childs, G.P.Stahly, A. Park, A.Mol. Pharmaceutics, 4 (2007) 323– 338. [2] S.J. Nehm, B. Rodríguez-Spong, N. Rodríguez-Hornedo, Cryst.Growth Des.6 (2006) 592−600. [3] M.L. Cheney, N. Shan, E.R. Healey, M. Hanna, Ł.Wojtas, M.J. Zaworotko, V. Sava, S. Song, J.R. Sanchez-Ramos, Cryst. Growt. Des. 10 (2010) 394–405. [4] A. Bak, A. Gore, E. Yanez, M. Stanton, S. Tufekcic, R. Syed, A. Akrami, M. Rose, S. Surapaneni, T. Bostick, A. King, S. Neervannan, D. Ostovic, A. Koparkar, J. Pharm. Sci. 97 (2008) 3942–3956. [5] S.L. Morissette, O. Almarsson, M.L. Peterson, J.F. Remenar, M.J. Read, A.V. Lemmo, S. Ellis, M.J. Cima, C.R. Gardner, Adv. Drug Deliv. Rev. 56 (2004) 275–300. [6] A. Cvetkovski, V. Ferretti, V. Bertolasi, Acta Cryst. C73 (2017) 1064–1070.

Item Type: Conference or Workshop Item (Poster)
Subjects: Medical and Health Sciences > Basic medicine
Engineering and Technology > Chemical engineering
Natural sciences > Chemical sciences
Engineering and Technology > Nano-technology
Divisions: Faculty of Medical Science
Depositing User: Aleksandar Cvetkovski
Date Deposited: 13 Nov 2020 09:50
Last Modified: 13 Nov 2020 09:50
URI: http://eprints.ugd.edu.mk/id/eprint/26727

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