Drug‐drug cocrystals of antituberculous 4‐aminosalicylic acid: Screening, crystal structures, thermochemical and solubility studies

Abstract Experimental multistage cocrystal screening of the antituberculous drug 4‐aminosalicylic acid (PASA) has been conducted with a number of coformers (pyrazinamide (PYR), nicotinamide (NAM), isonicotinamide (iNAM), isoniazid (INH), caffeine (CAF) and theophylline (TPH)). The crystal structures of 4‐aminosalicylic acid cocrystals with isonicotinamide ([PASA + iNAM] (2:1)) and methanol solvate with caffeine ([PASA + CAF + MeOH] (1:1:1)) have been determined by single X‐ray diffraction experiments. For the first time for PASA cocrystals it has been found that the structural unit of the [PASA + iNAM] cocrystal (2:1) is formed by 2 types of heterosynthons: acid‐pyridine and acid‐amide. The desolvation study of the [PASA + CAF + MeOH] cocrystal solvate (1:1:1) has been conducted. The correlation models linking the melting points of the cocrystals with the melting points of the coformers used in this paper have been developed. The thermochemical and solubility properties for all the obtained cocrystals have been studied. Cocrystallization has been shown to lead not only to PASA solubility improving but also to its higher stability against the chemical decomposition.

[1]  José A Fernandes,et al.  X-ray and NMR Crystallography Studies of Novel Theophylline Cocrystals Prepared by Liquid Assisted Grinding , 2015 .

[2]  N. Rodríguez-Hornedo,et al.  Pharmaceutical cocrystals and poorly soluble drugs. , 2013, International journal of pharmaceutics.

[3]  C. C. Seaton,et al.  Current directions in co-crystal growth , 2008 .

[4]  Pramod Kumar Goswami,et al.  Crystal Engineering of Multicomponent Crystal Forms of p-Aminosalicylic Acid with Pyridine Based Coformers , 2016 .

[5]  N. Báthori,et al.  Melting point–solubility–structure correlations in multicomponent crystals containing fumaric or adipic acid , 2014 .

[6]  A. P. Voronin,et al.  Cocrystal screening of hydroxybenzamides with benzoic acid derivatives: a comparative study of thermal and solution-based methods. , 2014, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[7]  Pramod Kumar Goswami,et al.  Multiple Crystal Forms of p-Aminosalicylic Acid: Salts, Salt Co-Crystal Hydrate, Co-Crystals, and Co-Crystal Polymorphs , 2013 .

[8]  A. Nangia,et al.  4-Aminosalicylic Acid Adducts , 2013 .

[9]  Evan W. Orenstein,et al.  Treatment outcomes among patients with multidrug-resistant tuberculosis: systematic review and meta-analysis. , 2009, The Lancet. Infectious diseases.

[10]  M. Zaworotko,et al.  Pharmaceutical cocrystals: along the path to improved medicines. , 2016, Chemical communications.

[11]  Ashwini Nangia,et al.  Solubility Advantage of Amorphous Drugs and Pharmaceutical Cocrystals , 2011 .

[12]  T. Gumbo,et al.  Treatment of Active Pulmonary Tuberculosis in Adults: Current Standards and Recent Advances , 2009, Pharmacotherapy.

[13]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[14]  G. Desiraju,et al.  Drug-drug co-crystals: Temperature-dependent proton mobility in the molecular complex of isoniazid with 4-aminosalicylic acid , 2011 .

[15]  B. S. Sekhon.  Drug-drug co-crystals , 2012, DARU Journal of Pharmaceutical Sciences.

[16]  A. Newman,et al.  Pharmaceutical Cocrystals and Their Physicochemical Properties , 2009, Crystal growth & design.

[17]  M. Caira.  Molecular complexes of sulfonamides. 2.1:1 complexes between drug molecules: sulfadimidine-acetylsalicylic acid and sulfadimidine-4-aminosalicylic acid , 1992 .

[18]  L. Fábián,et al.  Exploring cocrystal-cocrystal reactivity via liquid-assisted grinding: the assembling of racemic and dismantling of enantiomeric cocrystals. , 2006, Chemical communications.

[19]  J. Hoogmartens,et al.  Book Reviews : Who Expert Committee on Specifications for Pharmaceutical Preparations. Published by World Health Organisation, 1984. Price: Sw. fr. 6. Paperback. Pp 54. ISBN: 924 120704 3 , 1985, World Health Organization technical report series.

[20]  G. Perlovich.  Thermodynamic characteristics of cocrystal formation and melting points for rational design of pharmaceutical two-component systems , 2015 .

[21]  Paul W Smith,et al.  Perspective: Challenges and opportunities in TB drug discovery from phenotypic screening. , 2015, Bioorganic & medicinal chemistry.

[22]  Gargi Mukherjee,et al.  Polymorphs, Salts, and Cocrystals: What’s in a Name? , 2012 .

[23]  M. R. Silva,et al.  Pyrazinamide-Diflunisal: A New Dual-Drug Co-Crystal , 2011 .

[24]  S. Belyakov,et al.  Spontaneous cocrystal hydrate formation in the solid state: crystal structure aspects and kinetics , 2013 .

[25]  M. Caira,et al.  Structural relationships, thermal properties, and physicochemical characterization of anhydrous and solvated crystalline forms of tetroxoprim. , 2002, Journal of pharmaceutical sciences.

[26]  V. Stella,et al.  Mechanism of decarboxylation of p-aminosalicylic acid. , 1985, Journal of pharmaceutical sciences.

[27]  A. Nunn,et al.  Global tuberculosis drug development pipeline: the need and the reality , 2010, The Lancet.

[28]  Raj Suryanarayanan,et al.  A rapid thermal method for cocrystal screening , 2008 .

[29]  A. P. Voronin,et al.  Pharmaceutical salts of ciprofloxacin with dicarboxylic acids. , 2015, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[30]  A. V. Shishkina,et al.  Influence of Secondary Interactions on the Structure, Sublimation Thermodynamics, and Solubility of Salicylate:4-Hydroxybenzamide Cocrystals. Combined Experimental and Theoretical Study. , 2015, The journal of physical chemistry. B.