Physical Stability Enhancement and Pharmacokinetics of a Lithium Ionic Cocrystal with Glucose

Duggirala, Naga Kiran; Smith, Adam J. de; Wojtas, Łukasz; Shytle, R. Douglas; Zaworotko, Michael J.

doi:10.1021/cg501310d

Cited by 73 publications

(69 citation statements)

References 59 publications

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“…In the domain of multicomponent crystal form synthesis, CSP methods have shown to be a useful complementary tool in experimental efforts for the discovery of cocrystals 43 , hydrates 44 and salt hydrates. 24,45 The term ionic cocrystal (ICC) [46][47][48] has recently entered the crystal engineering lexicon to describe a multicomponent solid form where the crystal lattice consists of a salt and an additional chemical species which may be a neutral molecule or another salt complex. The existence of ICC solid forms has been known for a long time however, with some reports 48 suggesting that it was Kobell, who in 1843 first reported 49 an ICC consisting of sodium chloride and glucose.…”

Section: Introductionmentioning

confidence: 99%

Towards the systematic crystallisation of molecular ionic cocrystals: insights from computed crystal form landscapes

et al. 2018

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The underlying molecular and crystal properties affecting the crystallisation of ionic cocrystals (ICCs) with the general formula A-B+N (A- = anion, B+ = cation and N = neutral acid molecule; 1 : 1 : 1 stoichiometry) are reported for a limited set of known crystal structures determined following the cocrystallisation of either 4-aminopyridine (which forms salts) or 4-dimethylaminopyridine (which forms salts and ICCs) with the same set of monoprotic acids with a single hydroxy or halogen substitution at the ortho or para position. Periodic density functional theory calculations (PBE + D2) on the energetic driving force for ICC crystallisation for a set of known crystal structures with well characterised acid, salt and ICC structures show that all but 1 of the 7 experimental ICC structures surveyed were more stable than the sum of their component salt and acid structures with 4 displaying relative stabilities (ΔEICC) ranging from 2.47-8.02 kJ mol-1. The majority of molecular ICCs that are more stable with respect to their component salt and acid structures display the formation of discrete intermolecular O-HacidOanion hydrogen bonds with the D11(2) graph set between the carboxylic acid OH donor and the carboxylate oxygen acceptor of the anion. Computed crystal form landscapes for model 1 : 1 salts derived from acid-base pairs (involving 4-dimethylaminopyridine) known to form molecular ICCs show that on average the most stable predicted polymorphs of the 1 : 1 salts have efficient packing of the ions with packing coefficients in the range 65-80% and this is comparable to the packing coefficients of the most stable predicted polymorphs of 1 : 1 salts (involving 4-aminopyridine) that have no ICCs reported. This suggests that the cocrystallisation of equimolar amounts of the 1 : 1 salt and the acid to form a 1 : 1 : 1 molecular ICC is a complicated phenomenon that cannot be explained on the basis of inefficiencies in the crystal packing of the salt ions.

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Section: Introductionmentioning

confidence: 99%

Towards the systematic crystallisation of molecular ionic cocrystals: insights from computed crystal form landscapes

et al. 2018

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“…Co-crystals [1][2][3] are crystalline entities that comprise more than 1 component in a defined stoichiometric ratio and are held together by noncovalent interactions. Co-crystals of active pharmaceutical ingredients (APIs) show great promise in improving pharmaceutically relevant properties, such as dissolution, [4][5][6][7] bioavailability, [8][9][10][11] compressibility, 12,13 physical stability, [14][15][16][17] and photostability. 18,19 Thus, pharmaceutical companies are focusing on development aspects of co-crystals that include physicochemical characterization, [20][21][22] scale-up, 23,24 processing, and formulations of these novel materials.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Investigation of Carbamazepine-Saccharin Co-Crystal Polymorphs

Pagire

Jadav

Vangala

et al. 2017

Journal of Pharmaceutical Sciences

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Polymorphism in active pharmaceutical ingredients can be regarded as critical for the potential that crystal form can have on the quality, efficacy, and safety of the final drug product. The current contribution aims to characterize thermodynamic interrelationship of a dimorphic co-crystal, FI and FII, involving carbamazepine (CBZ) and saccharin (SAC) molecules. Supramolecular synthesis of CBZ-SAC FI and FII has been performed using thermokinetic methods and systematically characterized by differential scanning calorimetry, powder X-ray diffraction, solubility, and slurry measurements. According to the heat of fusion rule by Burger and Ramberger, FI (ΔH = 121.1 J/g; melting point, 172.5°C) and FII (ΔH = 110.3 J/g; melting point, 164.7°C) are monotropically related. The solubility and van't Hoff plot results suggest FI stable and FII metastable forms. This study reveals that CBZ-SAC co-crystal phases, FI or FII, could be stable to heat-induced stresses; however, FII converts to FI during solution-mediated transformation.

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“…Glucose has already been used as a GRAS compound in different models, for example to increase the stability of lithium salts as an improvement in the development of new lithium therapeutics. 69 Following this idea, and having proved that glucose can behave as a good exfoliating agent, we investigated the formation of possible glucose-graphene cocrystals.…”

Section: Mechanochemical Synthesis Of Graphene-glucose Cocrystalsmentioning

confidence: 99%

Sweet graphene: exfoliation of graphite and preparation of glucose-graphene cocrystals through mechanochemical treatments

et al. 2018

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Physical Stability Enhancement and Pharmacokinetics of a Lithium Ionic Cocrystal with Glucose

Cited by 73 publications

References 59 publications

Towards the systematic crystallisation of molecular ionic cocrystals: insights from computed crystal form landscapes

Towards the systematic crystallisation of molecular ionic cocrystals: insights from computed crystal form landscapes

Thermodynamic Investigation of Carbamazepine-Saccharin Co-Crystal Polymorphs

Sweet graphene: exfoliation of graphite and preparation of glucose-graphene cocrystals through mechanochemical treatments

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