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Статті в журналах з теми "Ionic cocrystals"

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Автор: Grafiati

Опубліковано: 10 грудня 2022

Оновлено: 28 січня 2023

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1

Mukherjee, Arijit, Robin D. Rogers, and A. S. Myerson. "Cocrystal formation by ionic liquid-assisted grinding: case study with cocrystals of caffeine." CrystEngComm 20, no. 27 (2018): 3817–21. http://dx.doi.org/10.1039/c8ce00859k.

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2

Patel, Diksha J., and Prashant K. Puranik. "Pharmaceutical Co-crystal : An Emerging Technique to enhance Physicochemical properties of drugs." International Journal of ChemTech Research 13, no. 3 (2020): 283–90. http://dx.doi.org/10.20902/ijctr.2019.130326.

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Анотація:

Major constraints in development of new product are poor aqueous solubility, stability and low oral bioavailability, low permeability. As majority of drugs marketed worldwide are administered by oral route and about 40% -50% of the new molecular entities were never invade into the market because of such biopharmaceutical issues.So issues related to poor physiochemical property of an active pharmaceutical ingredient (API) can be resolved using cocrystallization approach.Crystallization emerge as potential technique for enhancement of solubility of poorly aqueous soluble drugs also helps to improve physicochemical with preserving the pharmacological properties of the API . Cocrystals are solids that are crystalline single-phase materials composed of two or more different molecular and/or ionic compounds generally in a stoichiometric ratio which are neither solvates/hydrates nor simple salts. It is multicomponent system in which one component is API and another is called coformer. Coformer selection is the main challenging step during cocrystal synthesis , so various screening methods for the selection of coformers was explained . This article also summarizes differences between cocrystals with salts, solvates and hydrates along with the implications and limitations of cocrystals .It also provides a brief review on different methods of cocrystal formation and characterization techniuqes of cocrystals. Lastly this article highlights 85 synthetic and 14 herbal cocrystals along with its method of preparation and coformers used.

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3

Odiase, Isaac, Catherine E. Nicholson, Ruksanna Ahmad, Jerry Cooper, Dmitry S. Yufit, and Sharon J. Cooper. "Three cocrystals and a cocrystal salt of pyrimidin-2-amine and glutaric acid." Acta Crystallographica Section C Structural Chemistry 71, no. 4 (March 14, 2015): 276–83. http://dx.doi.org/10.1107/s2053229615004283.

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Four new cocrystals of pyrimidin-2-amine and propane-1,3-dicarboxylic (glutaric) acid were crystallized from three different solvents (acetonitrile, methanol and a 50:50 wt% mixture of methanol and chloroform) and their crystal structures determined. Two of the cocrystals, namely pyrimidin-2-amine–glutaric acid (1/1), C4H5N3·C6H8O4, (I) and (II), are polymorphs. The glutaric acid molecule in (I) has a linear conformation, whereas it is twisted in (II). The pyrimidin-2-amine–glutaric acid (2/1) cocrystal, 2C4H5N3·C6H8O4, (III), contains glutaric acid in its linear form. Cocrystal–salt bis(2-aminopyrimidinium) glutarate–glutaric acid (1/2), 2C4H6N3+·C6H6O42−·2C6H8O4, (IV), was crystallized from the same solvent as cocrystal (II), supporting the idea of a cocrystal–salt continuum when both the neutral and ionic forms are present in appreciable concentrations in solution. The diversity of the packing motifs in (I)–(IV) is mainly caused by the conformational flexibility of glutaric acid, while the hydrogen-bond patterns show certain similarities in all four structures.

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4

Rahmani, Maryam, Vijith Kumar, Julia Bruno-Colmenarez, and Michael J. Zaworotko. "Crystal Engineering of Ionic Cocrystals Sustained by Azolium···Azole Heterosynthons." Pharmaceutics 14, no. 11 (October 28, 2022): 2321. http://dx.doi.org/10.3390/pharmaceutics14112321.

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Анотація:

Crystal engineering of multi-component molecular crystals, cocrystals, is a subject of growing interest, thanks in part to the potential utility of pharmaceutical cocrystals as drug substances with improved properties. Whereas molecular cocrystals (MCCs) are quite well studied from a design perspective, ionic cocrystals (ICCs) remain relatively underexplored despite there being several recently FDA-approved drug products based upon ICCs. Successful cocrystal design strategies typically depend on strong and directional noncovalent interactions between coformers, as exemplified by hydrogen bonds. Understanding of the hierarchy of such interactions is key to successful outcomes in cocrystal design. We herein address the crystal engineering of ICCs comprising azole functional groups, particularly imidazoles and triazoles, which are commonly encountered in biologically active molecules. Specifically, azoles were studied for their propensity to serve as coformers with strong organic (trifluoroacetic acid and p-toluenesulfonic acid) and inorganic (hydrochloric acid, hydrobromic acid and nitric acid) acids to gain insight into the hierarchy of NH+···N (azolium-azole) supramolecular heterosynthons. Accordingly, we combined data mining of the Cambridge Structural Database (CSD) with the structural characterization of 16 new ICCs (11 imidazoles, 4 triazoles, one imidazole-triazole). Analysis of the new ICCs and 66 relevant hits archived in the CSD revealed that supramolecular synthons between identical azole rings (A+B−A) are much more commonly encountered, 71, than supramolecular synthons between different azole rings (A+B−C), 11. The average NH+···N distance found in the new ICCs reported herein is 2.697(3) Å and binding energy calculations suggested that hydrogen bond strengths range from 31–46 kJ mol−1. The azolium-triazole ICC (A+B−C) was obtained via mechanochemistry and differed from the other ICCs studied as there was no NH+···N hydrogen bonding. That the CNC angles in imidazoles and 1,2,4-triazoles are sensitive to protonation, the cationic forms having larger (approximately 4.4 degrees) values than comparable neutral rings, was used as a parameter to distinguish between protonated and neutral azole rings. Our results indicate that ICCs based upon azolium-azole supramolecular heterosynthons are viable targets, which has implications for the development of new azole drug substances with improved properties.

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5

Song, Lixing, Oleksii Shemchuk, Koen Robeyns, Dario Braga, Fabrizia Grepioni, and Tom Leyssens. "Ionic Cocrystals of Etiracetam and Levetiracetam: The Importance of Chirality for Ionic Cocrystals." Crystal Growth & Design 19, no. 4 (March 4, 2019): 2446–54. http://dx.doi.org/10.1021/acs.cgd.9b00136.

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6

McArdle, Patrick, and Andrea Erxleben. "Sublimation – a green route to new solid-state forms." CrystEngComm 23, no. 35 (2021): 5965–75. http://dx.doi.org/10.1039/d1ce00715g.

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7

Karothu, Durga Prasad, Ilma Jahović, Gligor Jovanovski, Branko Kaitner, and Panče Naumov. "Ionic cocrystals of molecular saccharin." CrystEngComm 19, no. 30 (2017): 4338–44. http://dx.doi.org/10.1039/c7ce00627f.

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Ionic cocrystals of molecular saccharin, one of the most commonly used artificial low-calorie sweeteners, where saccharin exists as a neutral species and an ion in the same crystal were synthesized and structurally characterized.

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8

Wang, Ting, Joanna S. Stevens, Thomas Vetter, George F. S. Whitehead, Iñigo J. Vitorica-Yrezabal, Hongxun Hao, and Aurora J. Cruz-Cabeza. "Salts, Cocrystals, and Ionic Cocrystals of a “Simple” Tautomeric Compound." Crystal Growth & Design 18, no. 11 (October 16, 2018): 6973–83. http://dx.doi.org/10.1021/acs.cgd.8b01159.

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9

Song, Lixing, Fucheng Leng, Koen Robeyns, and Tom Leyssens. "Quaternary phase diagrams as a tool for ionic cocrystallization: the case of a solid solution between a racemic and enantiopure ionic cocrystal." CrystEngComm 22, no. 14 (2020): 2537–42. http://dx.doi.org/10.1039/d0ce00179a.

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10

Mohamed, Sharmarke, Ahmad A. Alwan, Tomislav Friščić, Andrew J. Morris, and Mihails Arhangelskis. "Towards the systematic crystallisation of molecular ionic cocrystals: insights from computed crystal form landscapes." Faraday Discussions 211 (2018): 401–24. http://dx.doi.org/10.1039/c8fd00036k.

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11

Oertling, Heiko, Céline Besnard, Thibaut Alzieu, Mathieu Wissenmeyer, Claire Vinay, Julien Mahieux, and René Fumeaux. "Ionic Cocrystals of Sodium Chloride with Carbohydrates." Crystal Growth & Design 17, no. 1 (December 15, 2016): 262–70. http://dx.doi.org/10.1021/acs.cgd.6b01521.

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12

Nemec, Vinko, Katarina Lisac, Nikola Bedeković, Luka Fotović, Vladimir Stilinović, and Dominik Cinčić. "Crystal engineering strategies towards halogen-bonded metal–organic multi-component solids: salts, cocrystals and salt cocrystals." CrystEngComm 23, no. 17 (2021): 3063–83. http://dx.doi.org/10.1039/d1ce00158b.

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Анотація:

This highlight presents an overview of the current advances in the preparation of halogen bonded metal–organic multi-component solids, including salts and cocrystals comprising neutral and ionic constituents.

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13

Singh, Abhay Pratap, and Jubaraj B. Baruah. "Arrangements of fluorophores in the salts of imidazole tethered anthracene derivatives with pyridinedicarboxylic acids influencing photoluminescence." Materials Advances 3, no. 8 (2022): 3513–25. http://dx.doi.org/10.1039/d2ma00075j.

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Анотація:

Self-assemblies of salts of 9-N-(3-imidazolylpropylamino)methylanthracene with pyridinedicarboxylic acids, ionic-cocrystals with 1,3-dihydroxybenzene and their aggregation induced emissions in the solid state were studied.

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14

Gołdyn, Mateusz, Daria Larowska, Weronika Nowak, and Elżbieta Bartoszak-Adamska. "Synthon hierarchy in theobromine cocrystals with hydroxybenzoic acids as coformers." CrystEngComm 21, no. 48 (2019): 7373–88. http://dx.doi.org/10.1039/c9ce01195a.

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Анотація:

Cocrystals, solids composed of molecular and/or ionic compounds connected by noncovalent interactions, are objects of interest in crystal engineering. Theobromine, as an active pharmaceutical ingredient, was used in cocrystallization with dihydroxybenzoic acids.

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15

Buist, Amanda R., and Alan R. Kennedy. "Ionic Cocrystals of Pharmaceutical Compounds: Sodium Complexes of Carbamazepine." Crystal Growth & Design 14, no. 12 (November 12, 2014): 6508–13. http://dx.doi.org/10.1021/cg501400n.

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16

Smith, Adam J., Seol-Hee Kim, Naga K. Duggirala, Jingji Jin, Lukasz Wojtas, Jared Ehrhart, Brian Giunta, Jun Tan, Michael J. Zaworotko, and R. Douglas Shytle. "Improving Lithium Therapeutics by Crystal Engineering of Novel Ionic Cocrystals." Molecular Pharmaceutics 10, no. 12 (November 18, 2013): 4728–38. http://dx.doi.org/10.1021/mp400571a.

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17

Golovnev, N. N., M. S. Molokeev, I. V. Sterkhova, and I. I. Golovneva. "Structure of ionic cocrystals piperidinium 2-thiobarbiturate–2-thiobarbituric acid." Journal of Structural Chemistry 57, no. 6 (November 2016): 1266–69. http://dx.doi.org/10.1134/s0022476616060287.

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18

Lusi, Matteo, and Oisin Kavanagh. "Controlling the salt–cocrystal continuum and pKa rule: the multi-drug ionic cocrystals of lamatrigine and valproic acid." Acta Crystallographica Section A Foundations and Advances 75, a2 (August 18, 2019): e589-e589. http://dx.doi.org/10.1107/s2053273319089678.

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19

Hützler, Wilhelm Maximilian, Ernst Egert, and Michael Bolte. "6-Propyl-2-thiouracilversus6-methoxymethyl-2-thiouracil: enhancing the hydrogen-bonded synthon motif by replacement of a methylene group with an O atom." Acta Crystallographica Section C Structural Chemistry 72, no. 8 (July 20, 2016): 634–46. http://dx.doi.org/10.1107/s2053229616011281.

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The understanding of intermolecular interactions is a key objective of crystal engineering in order to exploit the derived knowledge for the rational design of new molecular solids with tailored physical and chemical properties. The tools and theories of crystal engineering are indispensable for the rational design of (pharmaceutical) cocrystals. The results of cocrystallization experiments of the antithyroid drug 6-propyl-2-thiouracil (PTU) with 2,4-diaminopyrimidine (DAPY), and of 6-methoxymethyl-2-thiouracil (MOMTU) with DAPY and 2,4,6-triaminopyrimidine (TAPY), respectively, are reported. PTU and MOMTU show a high structural similarity and differ only in the replacement of a methylene group (–CH2–) with an O atom in the side chain, thus introducing an additional hydrogen-bond acceptor in MOMTU. Both molecules contain anADAhydrogen-bonding site (A= acceptor andD= donor), while the coformers DAPY and TAPY both show complementaryDADsites and therefore should be capable of forming a mixedADA/DADsynthon with each other,i.e. N—H...O, N—H...N and N—H...S hydrogen bonds. The experiments yielded one solvated cocrystal salt of PTU with DAPY, four different solvates of MOMTU, one ionic cocrystal of MOMTU with DAPY and one cocrystal salt of MOMTU with TAPY, namely 2,4-diaminopyrimidinium 6-propyl-2-thiouracilate–2,4-diaminopyrimidine–N,N-dimethylacetamide–water (1/1/1/1) (the systematic name for 6-propyl-2-thiouracilate is 6-oxo-4-propyl-2-sulfanylidene-1,2,3,6-tetrahydropyrimidin-1-ide), C4H7N4+·C7H9N2OS−·C4H6N4·C4H9NO·H2O, (I), 6-methoxymethyl-2-thiouracil–N,N-dimethylformamide (1/1), C6H8N2O2S·C3H7NO, (II), 6-methoxymethyl-2-thiouracil–N,N-dimethylacetamide (1/1), C6H8N2O2S·C4H9NO, (III), 6-methoxymethyl-2-thiouracil–dimethyl sulfoxide (1/1), C6H8N2O2S·C2H6OS, (IV), 6-methoxymethyl-2-thiouracil–1-methylpyrrolidin-2-one (1/1), C6H8N2O2S·C5H9NO, (V), 2,4-diaminopyrimidinium 6-methoxymethyl-2-thiouracilate (the systematic name for 6-methoxymethyl-2-thiouracilate is 4-methoxymethyl-6-oxo-2-sulfanylidene-1,2,3,6-tetrahydropyrimidin-1-ide), C4H7N4+·C6H7N2O2S−, (VI), and 2,4,6-triaminopyrimidinium 6-methoxymethyl-2-thiouracilate–6-methoxymethyl-2-thiouracil (1/1), C4H8N5+·C6H7N2O2S−·C6H8N2O2S, (VII). Whereas in (I) only anAA/DDhydrogen-bonding interaction was formed, the structures of (VI) and (VII) both display the desiredADA/DADsynthon. Conformational studies on the side chains of PTU and MOMTU also revealed a significant deviation for cocrystals (VI) and (VII), leading to the desired enhancement of the hydrogen-bond pattern within the crystal.

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20

Gunnam, Anilkumar, Kuthuru Suresh, Ramesh Ganduri, and Ashwini Nangia. "Crystal engineering of a zwitterionic drug to neutral cocrystals: a general solution for floxacins." Chemical Communications 52, no. 85 (2016): 12610–13. http://dx.doi.org/10.1039/c6cc06627e.

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The transformation of zwitterionic Sparfloxacin (SPX) in its hydrate structure to a neutral anhydrate form is achieved by crystal engineering using the paraben coformer as the driver for proton migration. Here paraben acts as a “proton migrator” for the ionic to neutral transformation.

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21

Braga, Dario, Lorenzo Degli Esposti, Katia Rubini, Oleksii Shemchuk, and Fabrizia Grepioni. "Ionic Cocrystals of Racemic and Enantiopure Histidine: An Intriguing Case of Homochiral Preference." Crystal Growth & Design 16, no. 12 (November 21, 2016): 7263–70. http://dx.doi.org/10.1021/acs.cgd.6b01426.

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22

Petriček, Saša. "Pyridin-2-one in complexes, cocrystals and an ionic liquid. Syntheses, structures and thermal stability." Journal of Molecular Structure 1260 (July 2022): 132790. http://dx.doi.org/10.1016/j.molstruc.2022.132790.

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23

Shemchuk, Oleksii, Dario Braga, and Fabrizia Grepioni. "Ionic Cocrystals of Levodopa and Its Biological Precursors l-Tyrosine and l-Phenylalanine with LiCl." Crystal Growth & Design 19, no. 11 (September 17, 2019): 6560–65. http://dx.doi.org/10.1021/acs.cgd.9b01003.

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24

Singh, Munendra Pal, Arup Tarai, and Jubaraj Bikash Baruah. "Neutral, Zwitterion, Ionic Forms of 5‐Aminoisophthalic Acid in Cocrystals, Salts and Their Optical Properties." ChemistrySelect 4, no. 19 (May 16, 2019): 5427–36. http://dx.doi.org/10.1002/slct.201901111.

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25

Posavec, Lidija, Vinko Nemec, Vladimir Stilinović, and Dominik Cinčić. "Halogen and Hydrogen Bond Motifs in Ionic Cocrystals Derived from 3-Halopyridinium Halogenides and Perfluorinated Iodobenzenes." Crystal Growth & Design 21, no. 11 (October 13, 2021): 6044–50. http://dx.doi.org/10.1021/acs.cgd.1c00755.

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26

Duarte, Maria Teresa, Vânia André, Silvia Quaresma, and Inês Martins. "Pharma: improving and controlling properties. Cocrystals, bio-inspired MOFs and ionic liquids. Gabapentin, a case study." Acta Crystallographica Section A Foundations and Advances 72, a1 (August 28, 2016): s119. http://dx.doi.org/10.1107/s2053273316098247.

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27

Linberg, Kevin, Naveed Zafar Ali, Martin Etter, Adam A. L. Michalchuk, Klaus Rademann та Franziska Emmerling. "A Comparative Study of the Ionic Cocrystals NaX (α-d-Glucose)2 (X = Cl, Br, I)". Crystal Growth & Design 19, № 8 (10 липня 2019): 4293–99. http://dx.doi.org/10.1021/acs.cgd.8b01929.

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28

Song, Lixing, Koen Robeyns, and Tom Leyssens. "Crystallizing Ionic Cocrystals: Structural Characteristics, Thermal Behavior, and Crystallization Development of a Piracetam-CaCl2 Cocrystallization Process." Crystal Growth & Design 18, no. 5 (April 16, 2018): 3215–21. http://dx.doi.org/10.1021/acs.cgd.8b00352.

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29

Shunnar, Abeer F., Bhausaheb Dhokale, Durga Prasad Karothu, David H. Bowskill, Isaac J. Sugden, Hector H. Hernandez, Panče Naumov, and Sharmarke Mohamed. "Efficient Screening for Ternary Molecular Ionic Cocrystals Using a Complementary Mechanosynthesis and Computational Structure Prediction Approach." Chemistry – A European Journal 26, no. 21 (April 9, 2020): 4752–65. http://dx.doi.org/10.1002/chem.201904672.

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30

Tilborg, Anaëlle, Tom Leyssens, Bernadette Norberg, and Johan Wouters. "Structural Study of Prolinium/Fumaric Acid Zwitterionic Cocrystals: Focus on Hydrogen-Bonding Pattern Involving Zwitterionic (Ionic) Heterosynthons." Crystal Growth & Design 13, no. 6 (May 24, 2013): 2373–89. http://dx.doi.org/10.1021/cg400081v.

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31

Linberg, Kevin, Naveed Zafar Ali, Martin Etter, Adam A. L. Michalchuk, Klaus Rademann та Franziska Emmerling. "Correction to “A Comparative Study of the Ionic Cocrystals NaX (α-d-Glucose)2 (X = Cl, Br, I)”". Crystal Growth & Design 19, № 11 (жовтень 2019): 6822. http://dx.doi.org/10.1021/acs.cgd.9b01199.

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32

Bhogala, Balakrishna R., and Ashwini Nangia. "Cocrystals of 1,3,5-Cyclohexanetricarboxylic Acid with 4,4‘-Bipyridine Homologues: Acid···Pyridine Hydrogen Bonding in Neutral and Ionic Complexes." Crystal Growth & Design 3, no. 4 (July 2003): 547–54. http://dx.doi.org/10.1021/cg034047i.

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33

Shemchuk, Oleksii, Enrico Spoletti, Dario Braga, and Fabrizia Grepioni. "Solvent Effect on the Preparation of Ionic Cocrystals of dl-Amino Acids with Lithium Chloride: Conglomerate versus Racemate Formation." Crystal Growth & Design 21, no. 6 (April 30, 2021): 3438–48. http://dx.doi.org/10.1021/acs.cgd.1c00216.

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34

d’Agostino, Simone, Oleksii Shemchuk, Paola Taddei, Dario Braga, and Fabrizia Grepioni. "Embroidering Ionic Cocrystals with Polyiodide Threads: The Peculiar Outcome of the Mechanochemical Reaction between Alkali Iodides and Cyanuric Acid." Crystal Growth & Design 22, no. 4 (March 16, 2022): 2759–67. http://dx.doi.org/10.1021/acs.cgd.2c00202.

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35

André, Vânia, M. Teresa Duarte, Clara S. B. Gomes, and Mafalda C. Sarraguça. "Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis." Molecules 27, no. 1 (December 31, 2021): 241. http://dx.doi.org/10.3390/molecules27010241.

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Анотація:

In Portugal, publications with mechanochemical methods date back to 2009, with the report on mechanochemical strategies for the synthesis of metallopharmaceuticals. Since then, mechanochemical applications have grown in Portugal, spanning several fields, mainly crystal engineering and supramolecular chemistry, catalysis, and organic and inorganic chemistry. The area with the most increased development is the synthesis of multicomponent crystal forms, with several groups synthesizing solvates, salts, and cocrystals in which the main objective was to improve physical properties of the active pharmaceutical ingredients. Recently, non-crystalline materials, such as ionic liquids and amorphous solid dispersions, have also been studied using mechanochemical methods. An area that is in expansion is the use of mechanochemical synthesis of bioinspired metal-organic frameworks with an emphasis in antibiotic coordination frameworks. The use of mechanochemistry for catalysis and organic and inorganic synthesis has also grown due to the synthetic advantages, ease of synthesis, scalability, sustainability, and, in the majority of cases, the superior properties of the synthesized materials. It can be easily concluded that mechanochemistry is expanding in Portugal in diverse research areas.

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36

Alkhidir, Tamador, Zeinab M. Saeed, Abeer F. Shunnar, Eman Abujami, Runyararo M. Nyadzayo, Bhausaheb Dhokale, and Sharmarke Mohamed. "Expanding the Supramolecular Toolkit: Computed Molecular and Crystal Properties for Supporting the Crystal Engineering of Higher-Order Molecular Ionic Cocrystals." Crystal Growth & Design 22, no. 1 (December 13, 2021): 485–96. http://dx.doi.org/10.1021/acs.cgd.1c01107.

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37

Shemchuk, Oleksii, Fabrizia Grepioni, and Dario Braga. "Mechanochemical Preparation and Solid-State Characterization of 1:1 and 2:1 Ionic Cocrystals of Cyanuric Acid with Alkali Halides." Crystal Growth & Design 20, no. 11 (September 24, 2020): 7230–37. http://dx.doi.org/10.1021/acs.cgd.0c00899.

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38

Pal, Rumpa, Christian Jelsch, Lorraine A. Malaspina, Alison J. Edwards, M. Mangir Murshed, and Simon Grabowsky. "syn and anti polymorphs of 2,6-dimethoxy benzoic acid and its molecular and ionic cocrystals: Structural analysis and energetic perspective." Journal of Molecular Structure 1221 (December 2020): 128721. http://dx.doi.org/10.1016/j.molstruc.2020.128721.

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39

Avdeef, Alex, Elisabet Fuguet, Antonio Llinàs, Clara Ràfols, Elisabeth Bosch, Gergely Völgyi, Tatjana Verbić, Elena Boldyreva, and Krisztina Takács-Novák. "Equilibrium solubility measurement of ionizable drugs – consensus recommendations for improving data quality." ADMET and DMPK 4, no. 2 (June 29, 2016): 117. http://dx.doi.org/10.5599/admet.4.2.292.

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Анотація:

<p class="ADMETabstracttext">This commentary addresses data quality in equilibrium solubility measurement in aqueous solution. Broadly discussed is the “gold standard” shake-flask (SF) method used to measure equilibrium solubility of ionizable drug-like molecules as a function of pH. Many factors affecting the quality of the measurement are recognized. Case studies illustrating the analysis of both solution and solid state aspects of solubility measurement are presented. Coverage includes drug aggregation in solution (sub-micellar, micellar, complexation), use of mass spectrometry to assess aggregation in saturated solutions, solid state characterization (salts, polymorphs, cocrystals, polymorph creation by potentiometric method), solubility type (water, buffer, intrinsic), temperature, ionic strength, pH measurement, buffer issues, critical knowledge of the pK<sub>a</sub>, equilibration time (stirring and sedimentation), separating solid from saturated solution, solution handling and adsorption to untreated surfaces, solubility units, and tabulation/graphic presentation of reported data. The goal is to present cohesive recommendations that could lead to better assay design, to result in improved quality of measurements, and to impart a deeper understanding of the underlying solution chemistry in suspensions of drug solids.</p>

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40

Shamshina, Julia L., and Robin D. Rogers. "Are Myths and Preconceptions Preventing Us from Applying Ionic Liquid Forms of Antiviral Medicines to the Current Health Crisis?" International Journal of Molecular Sciences 21, no. 17 (August 20, 2020): 6002. http://dx.doi.org/10.3390/ijms21176002.

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At the moment, there are no U.S. Food and Drug Administration (U.S. FDA)-approved drugs for the treatment of COVID-19, although several antiviral drugs are available for repurposing. Many of these drugs suffer from polymorphic transformations with changes in the drug’s safety and efficacy; many are poorly soluble, poorly bioavailable drugs. Current tools to reformulate antiviral APIs into safer and more bioavailable forms include pharmaceutical salts and cocrystals, even though it is difficult to classify solid forms into these regulatory-wise mutually exclusive categories. Pure liquid salt forms of APIs, ionic liquids that incorporate APIs into their structures (API-ILs) present all the advantages that salt forms provide from a pharmaceutical standpoint, without being subject to solid-state matter problems. In this perspective article, the myths and the most voiced concerns holding back implementation of API-ILs are examined, and two case studies of API-ILs antivirals (the amphoteric acyclovir and GSK2838232) are presented in detail, with a focus on drug property improvement. We advocate that the industry should consider the advantages of API-ILs which could be the genesis of disruptive innovation and believe that in order for the industry to grow and develop, the industry should be comfortable with a certain element of risk because progress often only comes from trying something different.

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41

Torubaev, Yury V., Ivan V. Skabitsky, and Konstantin A. Lyssenko. "Structure-defining interactions in the salt cocrystals of [(Me5C5)2Fe]+I3−–XC6H4OH (X = Cl, I): weak noncovalent vs. strong ionic bonding." Mendeleev Communications 30, no. 5 (September 2020): 580–82. http://dx.doi.org/10.1016/j.mencom.2020.09.009.

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42

Das, Debarati, and Kumar Biradha. "Cocrystals and Salts of 3,5-Bis(pyridinylmethylene)piperidin-4-one with Aromatic Poly-Carboxylates and Resorcinols: Influence of Stacking Interactions on Solid-State Luminescence Properties." Australian Journal of Chemistry 72, no. 10 (2019): 742. http://dx.doi.org/10.1071/ch19062.

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Two bis-pyridyl-substituted α,β-unsaturated ketones were shown to form complexes with carboxylic acids and resorcinol derivatives. The neutral acid–acid homosynthon was observed in only one complex out of the five acid-bis-pyridyl containing complexes studied here, while the –COO−⋯HOOC– synthon was found to be dominant as it was observed in four complexes. The carboxylates self-assembled to form discrete dimeric, anionic, 1D chains and also exhibited mixed ionic hydrogen bonds. On the other hand, resorcinol derivatives displayed O–H⋯N hydrogen bonding to form tetrameric aggregates of bis-pyridyl ketone molecules and respective co-formers, while 3,5-dihydroxy benzoic acid (DHBA) molecules formed 1D chains by clipping two molecules of ketones with three DHBA molecules. Such clipping by the resorcinol derivatives promoted continuous π–π stacking interactions. Consequently, these materials emitted at higher wavelengths compared with the parent bis-pyridyl-substituted α,β-unsaturated ketones.

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43

Wzgarda-Raj, Kinga, Martyna Nawrot, Agnieszka J. Rybarczyk-Pirek, and Marcin Palusiak. "Ionic cocrystals of dithiobispyridines: the role of I...I halogen bonds in the building of iodine frameworks and the stabilization of crystal structures." Acta Crystallographica Section C Structural Chemistry 77, no. 8 (July 4, 2021): 458–66. http://dx.doi.org/10.1107/s2053229621006306.

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It has been confirmed that mercaptopyridines undergo spontaneous condensation in redox reaction with iodine-forming dithiopyridines. In the solid state, these compounds are protonated at the N atoms and cocrystallize with iodine forming salt structures, namely, 2-[(pyridin-2-yl)disulfanyl]pyridinium triiodide sesquiiodine, C10H9N2S2 +·I3 −·1.5I2, and 4,4′-(disulfanediyl)dipyridinium pentaiodide triiodide, C10H10N2S2 2+·I5 −·I3 −. Dithiopyridine cations are packed among three-dimensional frameworks built from iodide anions and neutral iodine molecules, and are linked by hydrogen, halogen and chalcogen interactions. Quantum chemical computations indicated that dithiopyridines exhibit anomalously high nitrogen basicity which qualify them as potential proton sponges.

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44

Nath, Jitendra, and Jubaraj B. Baruah. "Self-Assemblies of Solvates, Ionic Cocrystals, and a Salt Based on 4-{[(4-Nitrophenyl)carbamoyl]amino}-N-(pyrimidin-2-yl)benzene-1-sulfonamide: Study in the Solid and Solution States." Crystal Growth & Design 21, no. 9 (July 23, 2021): 5325–41. http://dx.doi.org/10.1021/acs.cgd.1c00643.

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45

Zhai, Pengfei, Chengying Shi, Shengxiang Zhao, Zongshu Mei, and Yinguang Pan. "Molecular dynamics simulations of a cyclotetramethylene tetra-nitramine/hydrazine 5,5′-bitetrazole-1,1′-diolate cocrystal." RSC Advances 9, no. 34 (2019): 19390–96. http://dx.doi.org/10.1039/c9ra02966d.

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46

Fowler, Drew A., Constance R. Pfeiffer, Simon J. Teat, Christine M. Beavers, Gary A. Baker, and Jerry L. Atwood. "Illuminating host–guest cocrystallization between pyrogallol[4]arenes and the ionic liquid 1-ethyl-3-methylimidazolium ethylsulfate." CrystEngComm 16, no. 27 (2014): 6010–22. http://dx.doi.org/10.1039/c4ce00359d.

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47

Iyan Sopyan, Tazyinul Qoriah Alfauziah, and Dolih Gozali. "Better in solubility enhancement : salt or cocrystal?" International Journal of Research in Pharmaceutical Sciences 10, no. 4 (October 16, 2019): 3013–25. http://dx.doi.org/10.26452/ijrps.v10i4.1589.

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Nowadays, most of marketed APIs are in the salt form. But not every single API was ionizable. Thus cocrystallization technique arised to overcome the problem. The aim of this review is to compare the solubility profile of salt and cocrystal. Both salt or cocrystal were used to improve the solubility of APIs and claimed for each other, which is the most effective in solubility enhancement. The salt was formed by ionic interaction, whilst cocrystal formed by hydrogen. Both interactions changed the interaction energy and crystal packing, thus changing the physicochemical properties of APIs. Besides, other factors affecting the solubility of the binary system were melting point, particle morphology, and solubility of coformer. The solubility comparison led to understand the underlying mechanism on solubility enhancement of salt and cocrystal itself.

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48

Rai, Sunil K., Debjani Baidya, and Ashwini K. Nangia. "Salts, solvates and hydrates of the multi-kinase inhibitor drug pazopanib with hydroxybenzoic acids." CrystEngComm 23, no. 35 (2021): 5994–6011. http://dx.doi.org/10.1039/d1ce00785h.

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Eight cocrystal-salts of the multi-kinase drug pazopanib with hydroxybenzoic acids are sustained by the strong, ionic aminopyridinium⋯carboxylate heterosynthon of N–H⋯O hydrogen bonds between the carboxylic acid donor and amino-pyrimidine acceptor.

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49

Khan, E., A. Shukla, N. Jadav, R. Telford, A. P. Ayala, P. Tandon, and V. R. Vangala. "Study of molecular structure, chemical reactivity and H-bonding interactions in the cocrystal of nitrofurantoin with urea." New Journal of Chemistry 41, no. 19 (2017): 11069–78. http://dx.doi.org/10.1039/c7nj01345k.

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50

Zhang, Xiaopeng, Shusen Chen, Yige Wu, Shaohua Jin, Xiaojun Wang, Yuqiao Wang, Fengqin Shang, Kun Chen, Junyi Du, and Qinghai Shu. "A novel cocrystal composed of CL-20 and an energetic ionic salt." Chemical Communications 54, no. 94 (2018): 13268–70. http://dx.doi.org/10.1039/c8cc06540c.

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A novel nitroamine/energetic ionic salt cocrystal explosive composed of CL-20 and 1-AMTN in a 1 : 1 molar ratio was discovered and characterized. It shows an appropriate explosive power and good mechanical sensitivity relative to RDX currently in use.

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