ACS Publications. Most Trusted. Most Cited. Most Read
Pharmaceutical Salts of Biologically Active Hydrazone Compound Salinazid: Crystallographic, Solubility, and Thermodynamic Aspects

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Crystal Growth & Design 2016, 16, 5, 2605-2617
    Article

    Pharmaceutical Salts of Biologically Active Hydrazone Compound Salinazid: Crystallographic, Solubility, and Thermodynamic Aspects
    Click to copy article linkArticle link copied!

    View Author Information
    † Institution of Russian Academy of Sciences, G.A. Krestov Institute of Solution Chemistry RAS, 153045, Ivanovo, Russia
    ‡ Institute of General and Inorganic Chemistry RAS, Leninskii Prosp. 31,119991, Moscow, Russia
    *E-mail [email protected]. Telephone: +7-4932-533784. Fax: +7-4932- 336237.
    Other Access OptionsSupporting Information (1)

    Crystal Growth & Design

    Cite this: Cryst. Growth Des. 2016, 16, 5, 2605–2617
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.cgd.5b01681
    Published March 30, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    The crystal structures of salts of the active pharmaceutical ingredient (API) called salinazid with dicarboxylic acids and acesulfame were determined by single-crystal X-ray diffraction method. The crystals contain hydrogen bond motifs of different structure and complexity, the energies of which were estimated by using the quantum theory of atoms in molecules and crystals (QTAIMC) methodology. It was found that the driving force for facile the oxalate and malate salts formation is the bifurcated N+–H···O– and N+–H···O hydrogen bond synthon, while salinazid malonate is mainly stabilized via a “classic” pyridinium-carboxylate heterosynthon. The oxalate and acesulfame salts of salinazid were found to be stable during aqueous dissolution experiments, providing a substantial solubility improvement compared to pure API (33 and 18 times, respectively). However, the malonate and malate salts dissolved incongruently and rapidly underwent a solution-mediated transformation to form pure salinazid. Based on the solubility data of the stable salts and of the pure components, the Gibbs free energy of the salts formation were calculated to be −21.2 kJ·mol–1 for salinazid oxalate and −22.6 kJ·mol–1 for salinazid acesulfame.

    Copyright © 2016 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.cgd.5b01681.

    • Complete tables of geometrical and electron density parameters; the energy of the strongest noncovalent interactions in the salt crystals; results of conformational analysis for oxalate ion and N-isonicotinoyl arylaldehydehydrazones derivatives; XRPD patterns of the residual materials after the salts solubility; crystallographic data for hydrated salt of salinazid with monomethyl oxalate (PDF)

    Accession Codes

    CCDC 1437855–1437859 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 21 publications.

    1. Alexander P. Voronin, Anna G. Ramazanova, Artem O. Surov, Andrei V. Churakov, German L. Perlovich. Multicomponent Crystals of Amitriptyline as Potential Controlled-Release Systems: Synthesis, Crystal Packing Analysis, and Dissolution Study. Crystal Growth & Design 2023, 23 (9) , 6926-6943. https://doi.org/10.1021/acs.cgd.3c00751
    2. Jun Qiu, Anisha Patel, Jason M. Stevens. High-Throughput Salt Screening of Synthetic Intermediates: Effects of Solvents, Counterions, and Counterion Solubility. Organic Process Research & Development 2020, 24 (7) , 1262-1270. https://doi.org/10.1021/acs.oprd.0c00132
    3. Qian Tao, Qian-Qian Hao, Alexander P. Voronin, Xia-Lin Dai, Yu Huang, German L. Perlovich, Tong-Bu Lu, Jia-Mei Chen. Polymorphic Forms of a Molecular Salt of Phenazopyridine with 3,5-Dihydroxybenzoic Acid: Crystal Structures, Theoretical Calculations, Thermodynamic Stability, and Solubility Aspects. Crystal Growth & Design 2019, 19 (10) , 5636-5647. https://doi.org/10.1021/acs.cgd.9b00618
    4. António O. L. Évora, Carlos E. S. Bernardes, M. Fátima M. Piedade, António C. L. Conceição, Manuel E. Minas da Piedade. Energetics of Glycine Cocrystal or Salt Formation with Two Regioisomers: Fumaric Acid and Maleic Acid. Crystal Growth & Design 2019, 19 (9) , 5054-5064. https://doi.org/10.1021/acs.cgd.9b00379
    5. Liliana Mazur, Ilona Materek, Andrew D. Bond, William Jones. Multicomponent Crystal Forms of a Biologically Active Hydrazone with Some Dicarboxylic Acids: Salts or Cocrystals?. Crystal Growth & Design 2019, 19 (5) , 2663-2678. https://doi.org/10.1021/acs.cgd.8b01795
    6. Inês C. B. Martins, Mariana Sardo, Edith Alig, Lothar Fink, Martin U. Schmidt, Luís Mafra, M. Teresa Duarte. Enhancing Adamantylamine Solubility through Salt Formation: Novel Products Studied by X-ray Diffraction and Solid-State NMR. Crystal Growth & Design 2019, 19 (3) , 1860-1873. https://doi.org/10.1021/acs.cgd.8b01830
    7. Sudhir Mittapalli, M. K. Chaitanya Mannava, Rasmita Sahoo, Ashwini Nangia. Cocrystals, Salts, and Supramolecular Gels of Nonsteroidal Anti-Inflammatory Drug Niflumic Acid. Crystal Growth & Design 2019, 19 (1) , 219-230. https://doi.org/10.1021/acs.cgd.8b01298
    8. Chenguang Wang, Sathyanarayana Reddy Perumalla, Changquan Calvin Sun. Anion Exchange Reaction for Preparing Acesulfame Solid Forms. Crystal Growth & Design 2018, 18 (8) , 4215-4219. https://doi.org/10.1021/acs.cgd.8b00106
    9. Jianhui Li, Xue Fu, Jiaoyang Li, Minmin Kong, Huaguang Yu, Jianming Wang, Zongwu Deng, and Hailu Zhang . Quinine Acesulfamates. Crystal Growth & Design 2017, 17 (1) , 58-66. https://doi.org/10.1021/acs.cgd.6b01145
    10. Harun Uslu, Basri Satilmiş, Ayşe Burçin Uyumlu, Begüm Nurpelin Sağlik, Serkan Levent, Yusuf Özkay, Metin Fikret Genç, Kadir Batçioğlu, Suat Kamişli, Kadriye Benkli. Development of Some Antiplatelet Salts as Drug Active Ingredients and Investigation Biological Activities. Pharmaceutical Chemistry Journal 2023, 57 (8) , 1260-1270. https://doi.org/10.1007/s11094-024-03032-1
    11. Archisman Dutta, Sourov Mondal, Pramod Kumar Singh, Biswajit Ray. Single crystal investigation, Hirshfeld surface and interaction energy framework analyses of structure-directing interactions within two isomorphous Schiff's base multicomponent salts. Journal of Molecular Structure 2022, 1264 , 133224. https://doi.org/10.1016/j.molstruc.2022.133224
    12. Reşit ÇAKMAK, Eyüp BAŞARAN. Benzoil Ester Grubu İçeren 2,4-Dinitrofenilhidrazin Temelli Bazı Yeni Hidrazon Bileşiklerinin Sentezi ve Yapısal Karakterizasyonu. Batman Üniversitesi Yaşam Bilimleri Dergisi 2022, 12 (1) , 79-91. https://doi.org/10.55024/buyasambid.1135813
    13. Balasubramanian Sridhar. Hydrogen bonding features of amide functionalities in four novel salts of an antiemetic drug domperidone. Journal of Molecular Structure 2021, 1232 , 129974. https://doi.org/10.1016/j.molstruc.2021.129974
    14. Artem O. Surov, Alexander P. Voronin, Nikita A. Vasilev, Andrey B. Ilyukhin, German L. Perlovich. Novel cocrystals of the potent 1,2,4-thiadiazole-based neuroprotector with carboxylic acids: virtual screening, crystal structures and solubility performance. New Journal of Chemistry 2021, 45 (6) , 3034-3047. https://doi.org/10.1039/D0NJ05644H
    15. Xin Chen, Duanxiu Li, Jianming Wang, Zongwu Deng, Hailu Zhang. Lenalidomide acesulfamate: Crystal structure, solid state characterization and dissolution performance. Journal of Molecular Structure 2019, 1175 , 852-857. https://doi.org/10.1016/j.molstruc.2018.08.059
    16. Alex N. Manin, Alexander P. Voronin, Ksenia V. Drozd, Andrei V. Churakov, German L. Perlovich. Pharmaceutical salts of emoxypine with dicarboxylic acids. Acta Crystallographica Section C Structural Chemistry 2018, 74 (7) , 797-806. https://doi.org/10.1107/S2053229618007386
    17. Adriana Ledeti, Gabriela Vlase, Titus Vlase, Denisa Circioban, Cristina Dehelean, Ionut Ledeti, Lenuta-Maria Suta. Binary adduct formation of desipramine with dicarboxylic acids. Journal of Thermal Analysis and Calorimetry 2018, 131 (1) , 167-173. https://doi.org/10.1007/s10973-016-5967-8
    18. Višnja Vrdoljak, Biserka Prugovečki, Ines Primožič, Tomica Hrenar, Danijela Cvijanović, Jelena Parlov Vuković, Renata Odžak, Mirjana Skočibušić, Stjepan Prugovečki, Jasna Lovrić, Dubravka Matković-Čalogović, Marina Cindrić. An integrated approach (synthetic, structural and biological) to the study of aroylhydrazone salts. New Journal of Chemistry 2018, 42 (14) , 11697-11707. https://doi.org/10.1039/C8NJ01457D
    19. Xian-Rui Zhang, Lei Zhang. Solvent effect on the self-assembly of salt solvates of an antihypertensive drug azilsartan and 2-methylimidazole. Journal of Molecular Structure 2017, 1137 , 320-327. https://doi.org/10.1016/j.molstruc.2017.02.063
    20. Vinayak Kamat, Krishna Naik, Vidyanand K. Revankar. Effect of acetate and nitrate anions on the molecular structure of 3-(hydroxyimino)-2-butanone-2-(1H-benzimidazol-2-yl)hydrazone. Journal of Molecular Structure 2017, 1133 , 546-556. https://doi.org/10.1016/j.molstruc.2016.12.044
    21. Minmin Kong, Xue Fu, Jiaoyang Li, Jianhui Li, Minhua Chen, Zongwu Deng, Hailu Zhang. Sweet pharmaceutical salts of stanozolol with enhanced solubility and physical stability. CrystEngComm 2016, 18 (45) , 8739-8746. https://doi.org/10.1039/C6CE01876A
    Download PDF
    Go to Crystal Growth & Design
    Get e-Alerts
    Get e-Alerts

    Crystal Growth & Design

    Cite this: Cryst. Growth Des. 2016, 16, 5, 2605–2617
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.cgd.5b01681
    Published March 30, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

    Article Views

    817

    Altmetric

    -

    Citations

    21
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.