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Article

Interconvertible Hydrochlorothiazide–Caffeine Multicomponent Pharmaceutical Materials: A Solvent Issue

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Laboratorio de Estudios Cristalográficos, IACT, CSIC-Universidad de Granada, Avda. de las Palmeras 4, 18100 Armilla, Spain
2
Servicio de Farmacia, Hospital Universitario de Jaén, 23007 Jaén, Spain
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Department of Chemistry, Universitat de les Illes Balears, Crta de Valldemossa km 7.5, 07122 Palma de Mallorca (Baleares), Spain
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Department of Inorganic Chemistry, Faculty of Pharmacy, University of Granada, 18071 Granada, Spain
*
Authors to whom correspondence should be addressed.
Crystals 2020, 10(12), 1088; https://doi.org/10.3390/cryst10121088
Received: 13 November 2020 / Revised: 25 November 2020 / Accepted: 26 November 2020 / Published: 27 November 2020
(This article belongs to the Special Issue Co-Crystals: From Discovery to Manufacture)
The design of new multicomponent pharmaceutical materials that involve different active pharmaceutical ingredients (APIs), e.g., drug-drug cocrystals, is a novel and interesting approach to address new therapeutic challenges. In this work, the hydrochlorothiazide-caffeine (HCT–CAF) codrug and its methanol solvate have been synthesized by mechanochemical methods and thoroughly characterized in the solid state by powder and single crystal X-ray diffraction, respectively, as well as differential scanning calorimetry, thermogravimetric analyses and infrared spectroscopy. In addition, solubility and stability studies have also been performed looking for improved physicochemical properties of the codrug. Interestingly, the two reported structures show great similarity, which allows conversion between them. The desolvated HCT–CAF cocrystal shows great stability at 24 h and an enhancement of solubility with respect to the reference HCT API. Furthermore, the contribution of intermolecular forces on the improved physicochemical properties was evaluated by computational methods showing strong and diverse H-bond and π–π stacking interactions. View Full-Text
Keywords: cocrystal; codrug; hydrochlorothiazide; caffeine; mechanochemical synthesis cocrystal; codrug; hydrochlorothiazide; caffeine; mechanochemical synthesis
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MDPI and ACS Style

Verdugo-Escamilla, C.; Alarcón-Payer, C.; Frontera, A.; Acebedo-Martínez, F.J.; Domínguez-Martín, A.; Gómez-Morales, J.; Choquesillo-Lazarte, D. Interconvertible Hydrochlorothiazide–Caffeine Multicomponent Pharmaceutical Materials: A Solvent Issue. Crystals 2020, 10, 1088. https://doi.org/10.3390/cryst10121088

AMA Style

Verdugo-Escamilla C, Alarcón-Payer C, Frontera A, Acebedo-Martínez FJ, Domínguez-Martín A, Gómez-Morales J, Choquesillo-Lazarte D. Interconvertible Hydrochlorothiazide–Caffeine Multicomponent Pharmaceutical Materials: A Solvent Issue. Crystals. 2020; 10(12):1088. https://doi.org/10.3390/cryst10121088

Chicago/Turabian Style

Verdugo-Escamilla, Cristóbal, Carolina Alarcón-Payer, Antonio Frontera, Francisco J. Acebedo-Martínez, Alicia Domínguez-Martín, Jaime Gómez-Morales, and Duane Choquesillo-Lazarte. 2020. "Interconvertible Hydrochlorothiazide–Caffeine Multicomponent Pharmaceutical Materials: A Solvent Issue" Crystals 10, no. 12: 1088. https://doi.org/10.3390/cryst10121088

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