In Situ Monitoring of Cocrystallization of Salicylic Acid–4,4′-Dipyridyl in Solution Using Raman Spectroscopy

In situ analysis using Raman spectroscopy was used to monitor the cocrystallization process. Raman spectroscopy in the cocrystallization of acetylsalicylic acid (ASA) and 4,4′-dipyridyl (4DP) in solution was investigated. A 2:1 salicylic acid (SAA)–4DP cocrystal was identified from crystallographic data obtained by X-ray single-crystal diffraction meter. In addition, Raman spectroscopy provided additional information on crystal structure of SAA–4DP cocrystal. Raman spectra peaks of ASA–4DP solution and SAA–4DP cocrystal were observed during crystallization. By the intensity of the peaks selected, nucleation and growth of cocrystal in solution were monitored. As a result, formation of new cocrystal using aspirin and 4DP was successfully monitored by Raman spectroscopy.

[1]  D. Kikelj,et al.  A 1:1 cocrystal of fluconazole with salicylic acid. , 2011, Acta crystallographica. Section C, Crystal structure communications.

[2]  Wei Wu,et al.  Enhanced dissolution of silymarin/polyvinylpyrrolidone solid dispersion pellets prepared by a one-step fluid-bed coating technique , 2008 .

[3]  Ana M. Belenguer,et al.  Real-time in situ powder X-ray diffraction monitoring of mechanochemical synthesis of pharmaceutical cocrystals. , 2013, Angewandte Chemie.

[4]  A. Kelly,et al.  Monitoring ibuprofen-nicotinamide cocrystal formation during solvent free continuous cocrystallization (SFCC) using near infrared spectroscopy as a PAT tool. , 2012, International journal of pharmaceutics.

[5]  Peter York,et al.  Use of in situ FT-Raman spectroscopy to study the kinetics of the transformation of carbamazepine polymorphs. , 2004, Journal of pharmaceutical and biomedical analysis.

[6]  Ulrich J. Griesser,et al.  Qualitative and quantitative study of polymorphic forms in drug formulations by near infrared FT-Raman spectroscopy , 2003 .

[7]  G. Desiraju,et al.  Five New Pseudopolymorphs of sym-Trinitrobenzene , 2003 .

[8]  H. Edwards,et al.  Identification of a new co-crystal of salicylic acid and benzamide of pharmaceutical relevance , 2010, Analytical and bioanalytical chemistry.

[9]  T. Row,et al.  Charge Density Analysis of Crystals of Nicotinamide with Salicylic Acid and Oxalic Acid: An Insight into the Salt to Cocrystal Continuum , 2010 .

[10]  Wei Wu,et al.  Enhanced dissolution and oral bioavailability of aripiprazole nanosuspensions prepared by nanoprecipitation/homogenization based on acid-base neutralization. , 2012, International journal of pharmaceutics.

[11]  A. Shete,et al.  Co-Crystals: A Novel Approach to Modify Physicochemical Properties of Active Pharmaceutical Ingredients , 2009, Indian journal of pharmaceutical sciences.

[12]  Wei Wu,et al.  Absorption, disposition and pharmacokinetics of nanoemulsions. , 2012, Current drug metabolism.

[13]  G. Desiraju,et al.  On the polymorphism of aspirin. , 2007, Angewandte Chemie.

[14]  Y. Pore,et al.  Improvement in physicochemical properties of ezetimibe using a crystal engineering technique , 2012 .

[15]  S. Onoue,et al.  Crystalline Form Information from Multiwell Plate Salt Screening by Use of Raman Microscopy , 2006, Pharmaceutical Research.

[16]  E. Perrier,et al.  Quantitative Analysis of Vitamin A Degradation by Raman Spectroscopy , 2003, Applied spectroscopy.

[17]  Lynne S. Taylor,et al.  Crystallization monitoring by Raman spectroscopy: Simultaneous measurement of desupersaturation profile and polymorphic form in flufenamic acid systems , 2005 .

[18]  S. Ibrić,et al.  Improvement of Aripiprazole Solubility by Complexation with (2-Hydroxy)propyl-β-cyclodextrin Using Spray Drying Technique , 2012, AAPS PharmSciTech.

[19]  Walkiria Schlindwein,et al.  In situ monitoring of carbamazepine-nicotinamide cocrystal intrinsic dissolution behaviour. , 2013, European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.

[20]  J. Chollet,et al.  Antifungal effects of salicylic acid and other benzoic acid derivatives towards Eutypa lata: structure-activity relationship , 2002 .