Multicomponent Crystal of Mefenamic Acid and N-Methyl-d-Glucamine: Crystal Structures and Dissolution Study

Zaini, Erizal; Fitriani, Lili; Sari, Risda Yulia; Rosaini, Henni; Horikawa, Ayano; Uekusa, Hidehiro

doi:10.1016/j.xphs.2019.02.003

Cited by 31 publications

(36 citation statements)

References 51 publications

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“…The melting point is correlated with the lattice energy of the crystal. A lower melting point indicates a weaker lattice energy in the crystalline phase, conferring greater solubility and a higher dissolution rate [34,47]. As described earlier, in the piperine-succinic acid cocrystal, succinic acid molecules formed a channel structure.…”

Section: Resultsmentioning

confidence: 80%

“…In general, a multicomponent crystal phase includes a salt, cocrystal, hydrate, and solvate [32,33]. Numerous studies have demonstrated that the formation of a multicomponent crystal phase of API with a suitable excipient could enhance its physicochemical properties, such as solubility and dissolution rate, permeability, bioavailability, physical stability, compressibility, and pharmacological efficacy [34][35][36][37][38][39]. To the best of our knowledge, only two studies on the multicomponent crystal phase of piperine have been reported: a cocrystal with resveratrol, and a salt with a halide [40,41].…”

Section: Introductionmentioning

confidence: 99%

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Improved Solubility and Dissolution Rates in Novel Multicomponent Crystals of Piperine with Succinic Acid

et al. 2020

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The objectives of this study were to prepare and characterize a novel piperine–succinic acid multicomponent crystal phase and to evaluate the improvement in the solubility and dissolution rate of piperine when prepared in the multicomponent crystal formation. The solid-state characterization of the novel multicomponent crystal was performed by powder X-ray diffraction (XRD), differential scanning calorimetry (DSC), and Fourier transform-infrared (FT-IR) spectroscopy. Solubility and dissolution rate profiles were evaluated in distilled water. The physical stability was evaluated under high relative humidity (75% and 100% RH). The determination of the single crystal X-ray diffraction structure revealed that this novel multicomponent crystal was a cocrystalline phase of piperine–succinic acid (2:1 molar ratio). The differential scanning calorimetry thermogram of the cocrystal showed a single and sharp endothermic peak at 110.49 °C. The cocrystal resulted in greater solubility and a faster dissolution rate of piperine than intact piperine. This improvement was a result of the formation of a channel structure in the cocrystal. In addition, the cocrystal was stable under a humid condition.

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Section: Resultsmentioning

confidence: 80%

Section: Introductionmentioning

confidence: 99%

Improved Solubility and Dissolution Rates in Novel Multicomponent Crystals of Piperine with Succinic Acid

et al. 2020

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“…Our previous finding has shown that MA can form salt type multicomponent crystal with N-Methyl-D-Glucamine with improved the dissolution rate and physical stability [22]. In the current study, we prepared multicomponent crystals of MA ( Fig.…”

Section: Introductionmentioning

confidence: 82%

“…Multicomponent crystals of pharmaceutical materials consist of co-crystal, salt, hydrate and solvate. Modification of physicochemical properties of an active pharmaceutical ingredient (API) via crystal engineering has become a popular approach because this approach can improve solubility, dissolution rate, compressibility, physical and chemical stability and pharmacological effectiveness [18][19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Multicomponent crystals of mefenamic acid-tromethamine with improved dissolution rate

Yuliandra¹,

Izadihari²,

Rosaini³

et al. 2019

Sanat

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Mefenamic acid (MA) is a popular nonsteroidal anti-inflammatory drug classified into BCS class II which has a low solubility and dissolution rate in an aqueous medium. The present study aimed to improve the dissolution rate of MA by preparing multicomponent crystals with tromethamine (TM) through the solvent evaporation technique. The resulting powder was characterized for its solid-state properties and evaluated for the dissolution rate. The results showed that the powder X-ray diffraction pattern of the MA-TM binary system was different from its starting materials, indicating the formation of a new crystalline phase. The differential scanning calorimetry analysis of the MA-TM binary system showed a single and sharp endothermic peak at 110 °C, which was attributed to the melting point of MA-TM multicomponent crystals. The Fourier transform infrared spectroscopy analysis showed the occurrence of solid-state interaction involving proton transfer between MA and TM. The dissolution efficiency of MA-TM multicomponent crystal was 2.5-fold higher than the intact MA. The study concludes that the MA-TM binary system forms a salt-type multicomponent crystal. The multicomponent crystals can significantly increase its dissolution rate and is an alternative technique for modifying the physicochemical properties of active pharmaceutical ingredients.

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“…Theoretically, the large difference of pKa between API molecule and counterion on pharmaceutical salt-affected solubility properties of API better than cocrystal (Zaini, 2019) . It was supported by (Banerjee, 2005) .…”

Section: Solubility Comparison Of Pharmaceutical Salt and Cocrystalsmentioning

confidence: 99%

Better in solubility enhancement : salt or cocrystal?

Alfauziah

Sopyan

2019

ijrps

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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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Multicomponent Crystal of Mefenamic Acid and N-Methyl-d-Glucamine: Crystal Structures and Dissolution Study

Cited by 31 publications

References 51 publications

Improved Solubility and Dissolution Rates in Novel Multicomponent Crystals of Piperine with Succinic Acid

Improved Solubility and Dissolution Rates in Novel Multicomponent Crystals of Piperine with Succinic Acid

Multicomponent crystals of mefenamic acid-tromethamine with improved dissolution rate

Better in solubility enhancement : salt or cocrystal?

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