Multicomponent crystals of gliclazide and tromethamine: preparation, physico-chemical, and pharmaceutical characterization

Bruni, Giovanna; Berbenni, Vittorio; Maggi, Lauretta; Mustarelli, Piercarlo; Friuli, Valeria; Ferrara, Chiara; Pardi, Francesca; Castagna, Federica; Girella, Alessandro; Milanese, Chiara; Marini, Amedeo

doi:10.1080/03639045.2017.1386208

Cited by 17 publications

(18 citation statements)

References 27 publications

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“…4). The endothermic peak at 170.5 °C, is the melting point of TM, whereas at 137.1 °C is a temperature of a solid-state transition [24]. The multicomponent crystal shows a single endothermic peak (110 °C) which is different from the two constituent components.…”

Section: Resultsmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

“…TM is a GRAS (generally recognized as safe) excipient according to FDA (the US Food and Drug Administration) and is widely used as an alkalizer and biological buffer. Moreover, TM is also used as a salt co-former for some weak acid drugs to improve the physicochemical properties [23,24]. To our knowledge,…”

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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“…The infrared absorption spectra of drug, coformer, and the cocrystal were obtained using FTIR spectrophotometer (IR Synthons in pharmaceutical cocrystals [16,17] a b…”

Section: Ftir Spectroscopymentioning

confidence: 99%

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Fatima¹

2018

AJP

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Context: Cocrystal technique is a novel approach for altering the physicochemical properties of an active pharmaceutical ingredient (API). Pharmaceutical cocrystals are formed by non-covalent interactions between an API and a coformer chosen from the generally recognized as safe (GRAS) substance list. Many examples exist in the literature where the cocrystal formations have led to the improvement in the dissolution of several APIs.Aims: Candesartan is a poorly water-soluble drug having an antihypertensive effect. The objective of the research work is to enhance the dissolution rate of candesartan through cocrystallization technique. Materials and Methods: Coformers were selected from the GRAS list after identifying the hydrogen bonding groups in the drug and the coformers. The coformers employed were were nicotinic acid, succinic acid, nicotinamide, and benzoic acid. Cocrystals were prepared using solution crystallization method. The differential scanning calorimetry obtained data showed the cocrystal formation with the coformer benzoic acid only. Further characterization was carried out by thermogravimetric analysis, Fourier-transform infrared, Raman spectroscopy, and powder X-ray diffraction studies. Thereafter, the cocrystal was subjected to solubility and dissolution studies. Statistical Analysis Used: The dissolution studies were subjected to t-test using SPSS 16. Results: The analytical data confirmed the formation of cocrystal. There was 1.78-fold enhancement in the solubility and its dissolution profile also improved. Conclusions: The solubility and in vitro dissolution studies clearly demonstrated that cocrystallization of candesartan with benzoic acid may be a potential approach for improving its aqueous solubility.

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“…Various approaches to improve the dissolution behaviour of GLZ have been pursued including micronization (Varshosaz et al, 2008), encapsulation into nanoparticles (Devarajan and Sonavane, 2007;Naik et al, 2013), dispersion into polymers (Hong et al, 1998;Biswal et al, 2008Biswal et al, , 2009aJondhale et al, 2012;Lu et al, 2017), salt formation (El-Sabawi and Hamdan, 2014;Putra et al, 2016a,b;Samie et al, 2017) and complexation with cyclodextrins (Winters et al, 1997;Özkan et al, 2000;Aggarwal et al, 2002). More recently, a limited number of studies on GLZ cocrystals were also reported (Chadha et al, 2016(Chadha et al, , 2017Samie et al, 2017;Bruni et al, 2018). Chadha and coworkers used the GRAS (Generally Recognized as Safe) coformers succinic acid, malic acid, sebatic acid and -hydroxyacetic acid to obtain multicomponent crystals of GLZ with enhanced dissolution properties (Chadha et al, 2016(Chadha et al, , 2017.…”

Section: Introductionmentioning

confidence: 99%

“…The cocrystallization of GLZ with catechol and resorcinol was studied by Desiraju and coworkers (Samie et al, 2017). Bruni et al reported a multicomponent crystal of GLZ and the excipient tromethamine (Bruni et al, 2018). Uekusa and coworkers cocrystallized GLZ with the antidiabetic drug metformin and obtained a salt with a significantly improved solubility and dissolution rate (Putra et al, 2016a).…”

Section: Introductionmentioning

confidence: 99%

Investigation of the formation of drug-drug cocrystals and coamorphous systems of the antidiabetic drug gliclazide

Aljohani

MacFhionnghaile

McArdle

et al. 2019

International Journal of Pharmaceutics

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The antidiabetic drug gliclazide (GLZ) has a slow absorption rate and a low bioavailability due to its poor solubility. GLZ is often prescribed along with an antihypertensive, as many diabetic patients have coexistent hypertension. Cocrystallization and coamorphization are attractive strategies to enhance dissolution rates and to reduce the number of medications a patient has to take. In this work the formation of cocrystals and coamorphous systems of GLZ with various antihypertensive drugs was studied, namely chlorothiazide (CTZ), hydrochlorothiazide (HTZ), indapamide (IND), triamterene (TRI) and nifedipine (NIF) as well as benzamidine (BZA) as a model for the amidine pharmacophore. TRI, IND and HTZ were found to form coamorphous systems with GLZ that are stable for at least six months at 22  2 C and 56 % relative humidity. Coamorphous GLZ-TRI is also stable in dissolution medium. Coamorphization of GLZ-TRI with 15 % sodium taurocholate gave a viable coamorphous formulation with an enhanced dissolution rate. Comilling of GLZ with BZA and cocrystallization from solution gave the amorphous and crystalline salt, respectively and the X-ray structure is reported. During attempts to obtain X-ray suitable cocrystals crystals of 2 Na + GLZand IND . 0.5H2O were obtained. Redetermination of the published structure of IND . 0.5H2O revealed a unit cell with the length of the a axis doubled, a different space group and no disorder. Liquid-assisted grinding of a 1:1 mixture of GLZ and IND indicated the transformation of IND to a new solid-state form, while GLZ remained unaltered. Milling-and heating-induced solid-state transformations of IND are discussed.

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Multicomponent crystals of gliclazide and tromethamine: preparation, physico-chemical, and pharmaceutical characterization

Abstract: The new system shows an improved pharmaceutical behavior and could be formulated in a dosage form to obtain a rapid and complete release of the drug available for absorption.

Cited by 17 publications

References 27 publications

Multicomponent crystals of mefenamic acid-tromethamine with improved dissolution rate

Multicomponent crystals of mefenamic acid-tromethamine with improved dissolution rate

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Investigation of the formation of drug-drug cocrystals and coamorphous systems of the antidiabetic drug gliclazide

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