Isostructurality in pharmaceutical salts: How often and how similar?

Wood, Peter A.; Oliveira, Mark A.; Zink, Andrina; Hickey, Magali B.

doi:10.1039/c2ce06588f

Cited by 30 publications

(29 citation statements)

References 33 publications

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“…A phenomenon that arises from crystallization of chemically similar molecules, and one that is also known to be common for organic compounds and salts, is isostructurality (Galcera et al, 2013;Wood et al, 2012;Dabros et al, 2007;James et al, 2012). Factors such as the balance between 'closepacking effects' and more directional and anisotropic intermolecular interactions during crystallization (Aakerö y et al, 2010) play an important role in the engineering of isostructural crystals.…”

Section: Introductionmentioning

confidence: 99%

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Omondi¹,

Lemmerer²,

Fernandes³

et al. 2013

Acta Crystallogr Sect B

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In order to investigate possible isostructural solid solutions of disubstituted N-phenylformamides and thioamides, we have studied the re-crystallization of pairs of compounds selected from 2,6-difluoro-N-phenylformamide (I), 2,6-dichloro-N-phenylformamide (II), 2,6-dimethyl-N-phenylformamide (III), 2,6-dichloro-N-phenylthioamide (IV), 2,6-dimethyl-N-phenylthioamide (V), 2,6-diisopropyl-N-phenylformamide (VI) and 2,6-diisopropyl-N-phenylthioamide (VII). For single-component 2,6-disubstituted-N-phenylformamides only the trans form occurs in the pure crystal, while for thioamides the cis form occurs, with only one exception. By forming solid solutions of pairs of these molecules the resulting structures all adopt similar N-H...O/S chains in the crystals. Solid solutions (1), (2) and (3), resulting from the mixing of (I) and (II), (II) and (III), and (IV) and (V), respectively, are all isostructural with each other (space group Pbca). Only co-crystal (1) is isostructural to both starting materials, while (2) is isostructural to only one of the starting pair, (II). Solid solution (3), which adopts the same Pbca structure as (1) and (2), is different to the monoclinic structures of both the reactants. Solid solution (4) is monoclinic, with similar hydrogen-bonded chains, and isostructural to the two components, resulting from the composition from the mixing of (VI) and (VII). Isostructural indices were used to quantify crystal-packing similarities and differences. Occupancy factors of the reactants in each co-crystal differ widely.

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Section: Introductionmentioning

confidence: 99%

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Omondi¹,

Lemmerer²,

Fernandes³

et al. 2013

Acta Crystallogr Sect B

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“…A recent study by Wood et al reported that isostructurality between sodium and potassium salts is common even though cell parameters tend to be slightly different. 44 Isostructurality was also observed in ICCS of seletracetam and brivaracetam with lithium bromide. 31 In our case the slight differences in cell parameters and PXRD patterns in the anhydrous forms (LIBGLU and XOZVOY) might be attributed to the relative size of the different counter ions (Cl -and Br -) and the different coordination geometries of the lithium (6, 5, 5) and sodium cations (all exhibit distorted octahedral geometry).…”

Section: Dynamic Vapor Analysis (Dvs)mentioning

confidence: 81%

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

Duggirala

Smith

Wojtas

et al. 2014

Crystal Growth & Design

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Current lithium drugs are plagued with a narrow therapeutic window and tend to be hygroscopic. However, they remain the gold standard for treating manic episodes in bipolar disorder. In this contribution, we report a crystal engineering study aimed at the preparation and characterization of ionic cocrystals (ICCs) of lithium chloride (LIC) and lithium bromide (LIB) with glucose (GLU). The structure of LIBGLU was studied by single crystal X-ray diffraction and found to be isostructural with related sodium chloride-glucose ICCs. The physical stability of LICGLU was compared to LIC at 50% RH and 25°C and through dynamic vapor sorption analysis. The blood and brain pharmacokinetics of LICGLU was compared to LIC in rat models and revealed little change in performance. This study reveals that ICCs can modestly improve solid form stability of lithium salts without impacting in vivo performance, a step towards enabling development of the next generation of lithium therapeutics.

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“…The cell similarity index (П) in this case is equal to 0.03 and the isostructurality index I(20) = 59.4%. However, these values (in particular the latter) are not fully representative as they are influenced by the big difference in size of the counterions [ 35 ]. The cell similarity indices for the pairs 1 and 3 and 2 and 3 , with a smaller, almost equal difference in size between the counterions, show П values of ca.…”

Section: Resultsmentioning

confidence: 99%

Counterion Effect and Isostructurality in a Series of Ag(I) Complexes Containing a Flexible, Imidazole Based Dipodal Ligand

Dobrzańska¹

2021

Materials

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The crystal structures of a series of Ag(I) complexes with 1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene (L) and the counterions BF4- (1), PF6- (2), ClO4- (3), and CF3SO3- (4) were analysed to determine the effect of the latter on their formation. All resulting compounds crystallise in the non-centrosymmetric space group Cc of a monoclinic system and show the formation of cationic, polymeric 1D Ag(I) complexes. SCXRD analyses revealed that compounds 1–3 are isostructural, though 1 shows opposite handedness compared to 2 and 3, resulting in an inversed packing arrangement. The presence of the larger, elongated triflate counterion in 4 leads to a different ligand conformation, as well as different arrangements of the ligand in the cationic chain, and simultaneously results in a packing that exhibits fewer similarities with the remaining three compounds.

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Isostructurality in pharmaceutical salts: How often and how similar?

Cited by 30 publications

References 33 publications

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

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

Counterion Effect and Isostructurality in a Series of Ag(I) Complexes Containing a Flexible, Imidazole Based Dipodal Ligand

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