Pharmaceutical cocrystals of ethenzamide: structural, solubility and dissolution studies

Aitipamula, Srinivasulu; Wong, Annie B. H.; Chow, Pui Shan; Tan, Reginald B. H.

doi:10.1039/c2ce26325d

Cited by 72 publications

(59 citation statements)

References 63 publications

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“…[15] Salicylates are not only used as APIs, but also as cocrystal formers. [18][19][20][21][22][23]. The most popular coformer is salicylic acid with 40 cocrystals.…”

Section: Scheme 1 Molecular Structure Of Salicylates and 4-hydroxybementioning

confidence: 99%

Influence of Secondary Interactions on the Structure, Sublimation Thermodynamics, and Solubility of Salicylate:4-Hydroxybenzamide Cocrystals. Combined Experimental and Theoretical Study

et al. 2015

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Cocrystal screening of 4-hydroxybenzamide with a number of salicylates (salicylic acid, SA; 4-aminosalicylic acid, PASA; acetylsalicylic acid, ASA; and salicylsalicylic acid, SSA) was conducted to confirm the formation of two cocrystals, [SA+4-OHBZA] (1:1) and [PASA+4-OHBZA] (1:1). Their structures were determined using single-crystal X-ray diffraction, and the hydrogen-bond network topology was studied. Thermodynamic characteristics of salicylic acid cocrystal sublimation were obtained experimentally. It was proved that PASA cocrystallization with 4-OHBZA makes the drug more stable and prevents the irreversible process of decarboxylation of PASA resulting in formation of toxic 3-aminophenol. The pattern of non-covalent interactions in the cocrystals is described quantitatively using solid-state density functional theory followed by Bader analysis of the periodic electron density. It has been found that the total energy of secondary interactions between synthon atoms and the side hydroxyl group of the acid molecule in [SA+4-OHBZA] (1:1) and [PASA+4-OHBZA] (1:1) cocrystals is comparable to the energy of the primary acid-amide heterosynthon. The theoretical value of the sublimation enthalpy of [SA+4-OHBZA], 231 kJ/mol, agrees fairly well with the experimental one, 272 kJ/mol. The dissolution experiments with [SA+4-OHBZA] have proved that the relatively large cocrystal stability in relation to the stability of its components has a negative effect on the dissolution rate and equilibrium solubility. The [PASA+4-OHBZA] (1:1) cocrystal showed an enhancement of apparent solubility compared to that of the corresponding pure active pharmaceutical ingredient, while their intrinsic dissolution rates are comparable.

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“…[15] Salicylates are not only used as APIs, but also as cocrystal formers. [18][19][20][21][22][23]. The most popular coformer is salicylic acid with 40 cocrystals.…”

Section: Scheme 1 Molecular Structure Of Salicylates and 4-hydroxybementioning

confidence: 99%

Influence of Secondary Interactions on the Structure, Sublimation Thermodynamics, and Solubility of Salicylate:4-Hydroxybenzamide Cocrystals. Combined Experimental and Theoretical Study

et al. 2015

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“…Also many other physicochemical properties can be modulated by cocrystallization including stability [21][22][23][24], hygroscopicity [25] and prolonged shelf life [26]. Among many drugs, aromatic amides acting either as APIs or as excipients attract nowadays substantial attention [27][28][29][30][31][32][33][34][35]. These compounds are known for their important roles in medical applications.…”

Section: Introductionmentioning

confidence: 99%

“…Although many pharmaceutical cocrystals containing amides have been studied [27][28][29][30][31][32][33][34][35], the data deposited in the Cambridge Structural Database (CSD) [41] are rather variable in the sense that many coformers were used for synthesis of diverse cocrystals. For example cocrystals of fumaric acid with benzamide, isonicotinamide or nicotinamide are known under refcodes YOPBUB, LUNNOX and EDAPOQ, respectively, but there is no information about solids of these coformers with temozolomide.…”

Section: Introductionmentioning

confidence: 99%

Transferability of cocrystallization propensities between aromatic and heteroaromatic amides

Cysewski

2016

Struct Chem

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New virtual cocrystal screening was proposed taking advantage of the similarities between cocrystallization landscapes of different compounds. Assuming that cocrystallization propensities can be modeled by miscibility affinities of liquid components under supercooled conditions, the quantitative rules of likeness were formulated and validated for 45 aromatic and heteroaromatic amides interacting with a variety of coformers. The most important finding comes from the observed linear trends between the values of mixing enthalpies of amides with respect to a reference molecule. Particularly isonicotinamide was found as a very convenient comparative system since it constitutes 97 binary cocrystals. Many experimentally observed cocrystals were used for supporting the analogy hypothesis, which states that a properly selected reference molecule, for which cocrystals were experimentally documented, can provide practical information about cocrystallization propensities of another compound provided that two criterions are met, namely sufficiently high similarities and high enough affinities. Hence, it is not necessary to perform experimental cocrystallization of every pair of coformers since miscibility in the solid state of one compound can be transferred to another one at least in the case of aromatic or heteroaromatic amides.

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“…The crystal forms are visually distinguishable as form I tends to form blocks whereas form II is needlelike. The transition between form II and form I is reportedly found between 60 and 100 °C, with a melting point of form I at 136 -140 °C [8,10,11]. The crystal structures of the two polymorphs have different conformations and can therefore be distinguished by infrared spectroscopy [8,11].…”

Section: Introductionmentioning

confidence: 98%

“…The crystal structures of the two polymorphs have different conformations and can therefore be distinguished by infrared spectroscopy [8,11]. In recent years, an increasing number of reports have appeared discussing the improvement of the physicochemical properties of CNBA with different molecules such as isonicotinic acid [12], isonicotinohydrazide [12], 3-cyanopyridine [13], 4-benzoylpyridine [14], p-anisidine [15], quinoline [16], ethenzamide [17], nicotinamide [7], pyrazine [18], mesitylene [9], p-xylene [9], acetophenone [9], dimethylsulfoxide [9], dioxane [9], 1,2,3 benzotriazole [19], including two salts: 3,5-dimethylpyridinium [20] and N'-isopropylideneisonicotinohydrazidium [12] and another compound with proton exchange in the liquid state: collidine [21]. Charge densities and other properties have also been studied for CNBA [22][23].…”

Section: Introductionmentioning

confidence: 99%

Fluorescence and physical properties of the organic salt 2-chloro-4-nitrobenzoate–3-ammonium-phenol

et al. 2015

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Pharmaceutical cocrystals of ethenzamide: structural, solubility and dissolution studies

Cited by 72 publications

References 63 publications

Influence of Secondary Interactions on the Structure, Sublimation Thermodynamics, and Solubility of Salicylate:4-Hydroxybenzamide Cocrystals. Combined Experimental and Theoretical Study

Influence of Secondary Interactions on the Structure, Sublimation Thermodynamics, and Solubility of Salicylate:4-Hydroxybenzamide Cocrystals. Combined Experimental and Theoretical Study

Transferability of cocrystallization propensities between aromatic and heteroaromatic amides

Fluorescence and physical properties of the organic salt 2-chloro-4-nitrobenzoate–3-ammonium-phenol

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