Pharmaceutical cocrystals, salts and polymorphs: Advanced characterization techniques

Advanced Drug Delivery Reviews - Tập 117 - Trang 111-146 - 2017
Edyta Pindelska1, Agnieszka Sokal1, Waclaw Kolodziejski1
1Medical University of Warsaw, Faculty of Pharmacy with the Laboratory Medicine Division, Department of Inorganic and Analytical Chemistry, Banacha 1, 02-093 Warsaw, Poland

Tài liệu tham khảo

FDA, 2016 Samie, 2017, Salts and cocrystals of antidiabetic drugs, gliclazide, tolbutamide and glipizide: solubility enhancements through drug−coformer interactions, Cryst. Growth Des., 17, 2406, 10.1021/acs.cgd.6b01804 Saini, 2016, New conformational polymorph of hydrochlorothiazide with improved solubility, Pharm. Dev. Technol., 21, 611, 10.3109/10837450.2015.1041040 Kalepu, 2015, Insoluble drug delivery strategies: review of recent advances and business prospects, Acta Pharm. Sin. B, 5, 442, 10.1016/j.apsb.2015.07.003 Serajuddin, 2007, Salt formation to improve drug solubility, Adv. Drug Deliv. Rev., 59, 603, 10.1016/j.addr.2007.05.010 Portell, 2009, Ziprasidone malate, a new trimorphic salt with improved aqueous solubility, CrystEngComm, 11, 791, 10.1039/b813401d Grothe, 2016, Solvates, salts, and cocrystals: a proposal for a feasible classification system, Cryst. Growth Des., 16, 3237, 10.1021/acs.cgd.6b00200 Elder, 2013, Use of pharmaceutical salts and cocrystals to address the issue of poor solubility, Int. J. Pharm., 453, 88, 10.1016/j.ijpharm.2012.11.028 Nie, 2017, Stability of pharmaceutical salts in solid oral dosage forms, Drug Dev. Ind. Pharm., 43, 1215, 10.1080/03639045.2017.1304960 Wöhler, 1844, Untersuchungen über das Chinon, Eur. J. Org. Chem., 51, 145 Aitipamula, 2012, Polymorphs, salts, and cocrystals: what's in a name?, Cryst. Growth Des., 12, 2147, 10.1021/cg3002948 Kuminek, 2016, How cocrystals of weakly basic drugs and acidic coformers might modulate solubility and stability, Chem. Commun., 52, 5832, 10.1039/C6CC00898D Bell, 2017, Chapter 17 regulatory considerations in dissolution and drug release of BCS class II and IV compounds, 573 Sanphui, 2015, Tuning mechanical properties of pharmaceutical crystals with multicomponent crystals: voriconazole as a case study, Mol. Pharm., 12, 889, 10.1021/mp500719t Singhal, 2004, Drug polymorphism and dosage form design: a practical perspective, Adv. Drug Deliv. Rev., 56, 335, 10.1016/j.addr.2003.10.008 Talaczynska, 2016, Benefits and limitations of polymorphic and amorphous forms of active pharmaceutical ingredients, Curr. Pharm. Des., 22, 4975, 10.2174/1381612822666160804100036 Haleblian, 1969, Pharmaceutical applications of polymorphism, J. Pharm. Sci., 58, 911, 10.1002/jps.2600580802 Friščić, 2013, Real-time and in situ monitoring of mechanochemical milling reactions, Nat. Chem., 5, 66, 10.1038/nchem.1505 Lin, 2015, Real-time co-crystal screening and formation between indomethacin and saccharin via DSC analytical technique or DSC–FTIR microspectroscopy, J. Therm. Anal. Calorim., 12, 679, 10.1007/s10973-014-3787-2 Harris, 2001, Contemporary advances in the use of powder X-ray diffraction for structure determination, Angew. Chem. Int. Ed., 40, 1626, 10.1002/1521-3773(20010504)40:9<1626::AID-ANIE16260>3.0.CO;2-7 Tremayne, 2004, The impact of powder diffraction on the structural characterization of organic crystalline materials, Philos. Trans. A. Math. Phys. Eng. Sci., 362, 2691, 10.1098/rsta.2004.1457 David, 2008, Structure determination from powder diffraction data, Acta Crystallogr. A Found. Crystallogr., 64, 52, 10.1107/S0108767307064252 Edwards, 1974 Aitipamula, 2011, Conformational polymorphs of a muscle relaxant, metaxalone, Cryst. Growth Des., 11, 4101, 10.1021/cg200678e Sanphui, 2016, New multi-component solid forms of anti-cancer drug erlotinib: role of auxiliary interactions in determining a preferred conformation, Acta Crystallogr. B Struct. Sci. Cryst. Eng. Mater., 72, 291, 10.1107/S2052520616003607 McCusker, 1999, Rietveld refinement guidelines, J. Appl. Crystallogr., 32, 36, 10.1107/S0021889898009856 Rietveld, 1969, A profile refinement method for nuclear and magnetic structures, J. Appl. Crystallogr., 2, 65, 10.1107/S0021889869006558 Werner, 1985, TREOR, a semi-exhaustive trial-and-error powder indexing program for all symmetries, J. Appl. Crystallogr., 18, 367, 10.1107/S0021889885010512 Boultif, 1991, Indexing of powder diffraction patterns for low-symmetry lattices by the successive dichotomy method, J. Appl. Crystallogr., 24, 987, 10.1107/S0021889891006441 Pawley, 1981, Unit-cell refinement from powder diffraction scans, J. Appl. Crystallogr., 14, 357, 10.1107/S0021889881009618 Le Bail, 1988, Ab-initio structure determination of LiSbWO6 by X-ray powder diffraction, Mater. Res. Bull., 23, 447, 10.1016/0025-5408(88)90019-0 Harris, 1994, Crystal structure determination from powder diffraction data by Monte Carlo methods, J. Am. Chem. Soc., 116, 3543, 10.1021/ja00087a047 David, 1998, Routine determination of molecular crystal structures from powder diffraction data, Chem. Commun., 8, 931, 10.1039/a800855h Kariuki, 1997, The application of a genetic algorithm for solving crystal structures from powder diffraction data, Chem. Phys. Lett., 280, 189, 10.1016/S0009-2614(97)01156-1 Seaton, 2002, Differential evolution: crystal structure determination of a triclinic polymorph of adipamide from powder diffraction data, Chem. Commun., 8, 880, 10.1039/b200436d Rietveld, 1967, Line profiles of neutron powder-diffraction peaks for structure refinement, Acta Crystallogr., 22, 151, 10.1107/S0365110X67000234 van de Streek, 2010, Validation of experimental molecular crystal structures with dispersion-corrected density functional theory calculations, Acta Crystallogr. B, B66, 544, 10.1107/S0108768110031873 van de Streek, 2014, Validation of molecular crystal structures from powder diffraction data with dispersion-corrected density functional theory (DFT-D), Acta Crystallogr. B., B70, 1020, 10.1107/S2052520614022902 Antonio, 2011, Quantitative phase analyses through the Rietveld method with X-ray powder diffraction data of heat-treated carbamazepine form III, J. Pharm. Sci., 100, 2658, 10.1002/jps.22482 Német, 2010, Rietveld refinement in the routine quantitative analysis of famotidine polymorphs, J. Pharm. Biomed. Anal., 51, 572, 10.1016/j.jpba.2009.09.017 Tiwari, 2007, Quantification of olanzapine polymorphs using powder X-ray diffraction technique, J. Pharm. Biomed. Anal., 43, 865, 10.1016/j.jpba.2006.08.030 Bernardi, 2013, Solid-state evaluation and polymorphic quantification of venlafaxine hydrochloride raw materials using the Rietveld method, Talanta, 117, 189, 10.1016/j.talanta.2013.09.006 Swapna, 2014, Cocrystals of the tuberculosis drug isoniazid: polymorphism, isostructurality, and stability, Cryst. Growth Des., 14, 5991, 10.1021/cg501182t Catalani, 1999, Review of the Indian market of anti-tuberculosis drugs: focus on the utilisation of rifampicin-based products, Int. J. Tuberc. Lung Dis., 3, S289 Iseman, 2002, Tuberculosis therapy: past, present and future, Eur. Respir. J., 20, 87S, 10.1183/09031936.02.00309102 Bag, 2012, Screening and selective preparation of polymorphs by fast evaporation method: a case study of aspirin, anthranilic acid, and niflumic acid, Cryst. Growth Des., 12, 2740, 10.1021/cg300404r Gonzaga, 2016, Solid-state phase transition mechanism and physical–chemical study of the crystal forms of monosodium alendronate: trihydrate versus anhydrate, Cryst. Growth Des., 12, 6891, 10.1021/acs.cgd.6b01064 Vega, 1996, Monosodium 4-amino-1-hydroxy-1, 1-butanediyldiphosphonate trihydrate (alendronate), Acta Crystallogr. C Cryst. Struct. Commun., 52, 2198, 10.1107/S0108270196006105 Asnani, 2009, Ab initio structure determination of anhydrous sodium alendronate from laboratory powder X-ray diffraction data, J. Pharm. Sci., 98, 2113, 10.1002/jps.21561 Matsumoto, 1991, Effects of temperature and pressure during compression on polymorphic transformation and crushing strength of chlorpropamide tablets, J. Pharm. Pharmacol., 43, 74, 10.1111/j.2042-7158.1991.tb06635.x Otsuka, 1995, Effect of compression temperature on the consolidation mechanism of chlorpropamide polymorphs, J. Pharm. Sci., 84, 614, 10.1002/jps.2600840517 Boldyreva, 2006, Effect of pressure up to 5.5GPa on dry powder samples of chlorpropamide form-A, Int. J. Pharm., 327, 51, 10.1016/j.ijpharm.2006.07.019 Yin, 2016, Visualization and quantification of deformation behavior of clopidogrel bisulfate polymorphs during tableting, Sci Rep, 6, 21770, 10.1038/srep21770 Halasz, 2013, Real-time in situ powder X-ray diffraction monitoring of mechanochemical synthesis of pharmaceutical cocrystals, Angew. Chem. Int. Ed., 52, 11538, 10.1002/anie.201305928 Maddileti, 2015, Tetramorphs of the antibiotic drug trimethoprim: characterization and stability, Cryst. Growth Des., 15, 1745, 10.1021/cg501772t Thomas, 2016, Selective preparation of elusive and alternative single component polymorphic solid forms through multi-component crystallisation routes, Chem. Commun., 52, 7372, 10.1039/C6CC01027J Babu, 2010, Conformational and synthon polymorphism in furosemide (Lasix), Cryst. Growth Des., 10, 1979, 10.1021/cg100098z Karanam, 2011, New polymorphs of fluconazole: results from cocrystallization experiments, Cryst. Growth Des., 12, 240, 10.1021/cg201005y Bond, 2007, On the polymorphism of aspirin: crystalline aspirin as intergrowths of two “polymorphic” domains, Angew. Chem. Int. Ed., 46, 618, 10.1002/anie.200603373 Bond, 2007, On the polymorphism of aspirin, Angew. Chem. Int. Ed., 46, 615, 10.1002/anie.200602378 Howard, 2014, Cutting-edge techniques used for the structural investigation of single crystals, Science, 343, 1098, 10.1126/science.1247252 Giacovazzo, 2011, vol. 7 Clegg, 2009 Hammond, 2009 Braga, 2007 Hoser, 2009, Towards the best model for H atoms in experimental charge-density refinement, Acta Crystallogr. A Found. Crystallogr., 65, 300, 10.1107/S0108767309019862 Woińska, 2016, Hydrogen atoms can be located accurately and precisely by x-ray crystallography, Sci. Adv., 2, 10.1126/sciadv.1600192 Jayatilaka, 2008, X-ray structure refinement using aspherical atomic density functions obtained from quantum-mechanical calculations, Acta Crystallogr. A Found. Crystallogr., 64, 383, 10.1107/S0108767308005709 Capelli, 2014, Hirshfeld atom refinement, IUCrJ, 1, 361, 10.1107/S2052252514014845 Sovago, 2016, Electron density, disorder and polymorphism: high-resolution diffraction studies of the highly polymorphic neuralgic drug carbamazepine, Acta Cryst, B72, 39 Orben, 2014, Hydrogen ADPs with Cu Kα data? Invariom and Hirshfeld atom modelling of fluconazole, Acta Crystallogr. C Struct. Chem., 70, 580, 10.1107/S2053229614010195 Boldyreva, 2010 Okumura, 2006, Polymorphic transformation of indomethacin under high pressures, J. Pharm. Sci., 95, 689, 10.1002/jps.20557 Boldyreva, 2002, Effect of high pressure on the polymorphs of paracetamol, J. Therm. Anal. Calorim., 68, 437, 10.1023/A:1016079400592 Ogienko, 2011, A new method of producing monoclinic paracetamol suitable for direct compression, Pharm. Res., 28, 3116, 10.1007/s11095-011-0502-x Fabbiani, 2003, Pressure-induced formation of a solvate of paracetamol, Chem. Commun., 24, 3004, 10.1039/b310394c Drebushchak, 2008, Two polymorphs of chlorpropamide: the δ-form and the high-temperature∊-form, Acta Crystallogr. C Cryst. Struct. Commun., 64, 0623, 10.1107/S0108270108034550 Olejniczak, 2016, Pressure-stabilized solvates of xylazine hydrochloride, Cryst. Growth Des., 16, 3756, 10.1021/acs.cgd.6b00264 Neumann, 2015, Combined crystal structure prediction and high-pressure crystallization in rational pharmaceutical polymorph screening, Nat. Commun., 6, 10.1038/ncomms8793 Hirshfeld, 1977, Bonded-atom fragments for describing molecular charge densities, Theor. Chem. Accounts, 44, 129, 10.1007/BF00549096 Spackman, 2009, Hirshfeld surface analysis, CrystEngComm, 11, 19, 10.1039/B818330A McKinnon, 1998, Hirshfeld surfaces: a new tool for visualising and exploring molecular crystals, Chem. Eur. J., 4, 2136, 10.1002/(SICI)1521-3765(19981102)4:11<2136::AID-CHEM2136>3.0.CO;2-G McKinnon, 2004, Novel tools for visualizing and exploring intermolecular interactions in molecular crystals, Acta Crystallogr. B Struct. Sci., 60, 627, 10.1107/S0108768104020300 Vella-Zarb, 2013, The devil is in the detail: a rare H-bonding motif in new forms of docetaxel, Cryst. Growth Des., 13, 4402, 10.1021/cg400814a Baisch, 2014, Towards understanding P-gp resistance: a case study of the antitumour drug cabazitaxel, CrystEngComm, 16, 10161, 10.1039/C4CE01279H Bond, 2007, What is a polymorph? Aspirin as a case study, Am. Pharm. Rev., 10, 24 Martins, 2009, Conformational polymorphism in racemic crystals of the diuretic drug chlortalidone, Cryst. Growth Des., 9, 3235, 10.1021/cg801322x Bolla, 2014, Pentamorphs of acedapsone, Cryst. Growth Des., 14, 5260, 10.1021/cg5010424 Surov, 2015, Diversity of felodipine solvates: structure and physicochemical properties, CrystEngComm, 17, 4089, 10.1039/C5CE00350D Saikia, 2015, Hydrogen bond synthons in the interplay of solubility and membrane permeability/diffusion in variable stoichiometry drug cocrystals, Cryst.Growth Des., 15, 5593, 10.1021/acs.cgd.5b01293 Smith, 2005 Stuart, 2007 2007 2010 Hamm, 2011 2013 2014 Ciurczak, 2015 Diem, 2015 2008 Stejskal, 1994 Duer, 2005 2008 2009 Apperley, 2012 Bugay, 2001, Characterization of the solid-state: spectroscopic techniques, Adv. Drug Deliv. Rev., 48, 43, 10.1016/S0169-409X(01)00101-6 Threlfall, 2006, 3557 Clark, 2007, The analysis of pharmaceutical substances and formulated products by vibrational spectroscopy, 1 Van Eerdenbrugh, 2011, Application of mid-IR spectroscopy for the characterization of pharmaceutical systems, Int. J. Pharm., 417, 3, 10.1016/j.ijpharm.2010.12.011 Jamrógiewicz, 2012, Application of the near-infrared spectroscopy in the pharmaceutical technology, J. Pharm. Biomed. Anal., 66, 1, 10.1016/j.jpba.2012.03.009 Patel, 2010, An overview: application of Raman spectroscopy in pharmaceutical field, Curr. Pharm. Anal., 6, 131, 10.2174/157341210791202654 Paudel, 2015, Raman spectroscopy in pharmaceutical product design, Adv. Drug Deliv. Rev., 89, 3, 10.1016/j.addr.2015.04.003 Baxter, 2011, Terahertz spectroscopy, Anal. Chem., 83, 4342, 10.1021/ac200907z Shen, 2011, Terahertz pulsed spectroscopy and imaging for pharmaceutical applications: a review, Int. J. Pharm., 417, 48, 10.1016/j.ijpharm.2011.01.012 Ajito, 2012, Visualization of pharmaceutical drug molecules by terahertz chemical imaging, NTT Tech. Rev., 10, 1 Laws, 2002, Solid-state NMR spectroscopic methods in chemistry, Angew. Chem. Int. Ed., 41, 3096, 10.1002/1521-3773(20020902)41:17<3096::AID-ANIE3096>3.0.CO;2-X Harris, 2006, NMR studies of organic polymorphs & solvates, Analyst, 131, 351, 10.1039/b516057j Potrzebowski, 2008, 1 Geppi, 2008, Solid-state NMR studies of pharmaceutical systems, Appl. Spectrosc. Rev., 43, 202, 10.1080/05704920801944338 Vogt, 2009, Solid-state NMR analysis of organic cocrystals and complexes, Cryst. Growth Des., 9, 921, 10.1021/cg8007014 Vogt, 2010, Evolution of solid-state NMR in pharmaceutical analysis, Future Med. Chem., 2, 915, 10.4155/fmc.10.200 Middleton, 2013, Solid-state NMR spectroscopy in drug design and discovery, 1529 Monti, 2014, Solid-state NMR in pharmaceutical compounds, Annu. Rep. NMR Spectrosc., 83, 221, 10.1016/B978-0-12-800183-7.00004-6 Ayala, 2006, Solid state characterization of olanzapine polymorphs using vibrational spectroscopy, Int. J. Pharm., 326, 69, 10.1016/j.ijpharm.2006.07.023 Zimmermann, 2011, Thermal analysis of paracetamol polymorphs by FT-IR spectroscopies, J. Pharm. Biomed. Anal., 54, 295, 10.1016/j.jpba.2010.08.023 Ivanova, 2007, Linear-dichroic infrared spectroscopy - validation and experimental design of the new orientation technique of solid samples as suspension in nematic liquid crystal, Spectrochim. Acta A, 67, 66, 10.1016/j.saa.2006.06.025 Ivanova, 2005, Monoclinic and orthorhombic polymorphs of paracetamol - solid state linear dichroic infrared spectral analysis, J. Mol. Struct., 738, 233, 10.1016/j.molstruc.2004.12.036 Koleva, 2006, Polymorphs of aspirin - solid-state IR-LD spectroscopic and quantitative determination in solid mixtures, J. Mol. Struct., 800, 23, 10.1016/j.molstruc.2006.03.088 Ivanova, 2006, Solid state linear-dichroic infrared (IR-LD) spectroscopic characterization of α- and β-glycine polymorphs, Cent. Eur. J. Chem., 4, 111 Chapkanov, 2010, l-Valine and l-proline - solid-state IR-LD spectroscopic study, Protein Pept. Lett., 17, 347, 10.2174/092986610790780297 Hunt, 2009, 2D-IR spectroscopy: ultrafast insights into biomolecule structure and function, Chem. Soc. Rev., 38, 1837, 10.1039/b819181f Rubtsov, 2009, Relaxation-assisted two-dimensional infrared (RA 2DIR) method: accessing distances over 10Å and measuring bond connectivity patterns, Acc. Chem. Res., 42, 1385, 10.1021/ar900008p Le Sueur, 2015, Applications of two-dimensional infrared spectroscopy, Analyst, 140, 4336, 10.1039/C5AN00558B Chen, 2013, Molecular conformations of crystalline l-cysteine determined with vibrational cross angle measurements, J. Phys. Chem. B, 117, 15614, 10.1021/jp406232k Lin, 2013, Theophylline-citric acid co-crystals easily induced by DSC-FTIR microspectroscopy or different storage conditions, Asian J. Pharm. Sci., 8, 19, 10.1016/j.ajps.2013.07.003 Sato, 2017, Solid-state vibrational circular dichroism spectra of isoleucine and its related compounds: effects of interplay between two chiral centers, Chem. Lett., 46, 449, 10.1246/cl.161043 Bechtel, 2014, Ultrabroadband infrared nanospectroscopic imaging, PNAS, 111, 7191, 10.1073/pnas.1400502111 Muller, 2015, Infrared chemical nano-imaging: accessing structure, coupling, and dynamics on molecular length scales, J. Phys. Chem. Lett., 6, 1275, 10.1021/acs.jpclett.5b00108 Muller, 2016, Infrared vibrational nano-crystallography and nano-imaging, Sci. Adv., 2, 10.1126/sciadv.1601006 Amenabar, 2017, Hyperspectral infrared nanoimaging of organic samples based on Fourier transform infrared nanospectroscopy, Nat. Commun., 8, 14402, 10.1038/ncomms14402 Dazzi, 2017, AFM-IR: technology and applications in nanoscale infrared spectroscopy and chemical imaging, Chem. Rev., 117, 5146, 10.1021/acs.chemrev.6b00448 Marinkovic, 2005, Synchrotron infrared microspectroscopy, vol. 13, 671 Wang, 2013, Mercury-cadmium-telluride waveguides − a novel strategy for on-chip mid-infrared sensors, Anal. Chem., 85, 10648, 10.1021/ac4025544 Sorak, 2012, New developments and applications of handheld Raman, mid-infrared, and near-infrared spectrometers, Appl. Spectrosc. Rev., 47, 83, 10.1080/05704928.2011.625748 Kee, 2009, Selective crystallization of the metastable anhydrate form in the enantiotropic pseudo-dimorph system of l-phenylalanine using concentration feedback control, Cryst. Growth Des., 9, 3052, 10.1021/cg8006537 Rajalahti, 2011, Multivariate data analysis in pharmaceutics: a tutorial review, Int. J. Pharm., 417, 280, 10.1016/j.ijpharm.2011.02.019 Roggo, 2007, A review of near infrared spectroscopy and chemometrics in pharmaceutical technologies, J. Pharm. Biomed. Anal., 44, 683, 10.1016/j.jpba.2007.03.023 Li, 2012, Rapid and nondestructive analysis of pharmaceutical products using near-infrared diffuse reflectance spectroscopy, J. Pharm. Biomed. Anal., 70, 288, 10.1016/j.jpba.2012.07.013 Luypaert, 2007, Near-infrared spectroscopy applications in pharmaceutical analysis, Talanta, 72, 865, 10.1016/j.talanta.2006.12.023 Räsänen, 2007, NIR spectroscopy in the development of solid dosage forms, J. Pharm. Pharmacol., 59, 147, 10.1211/jpp.59.2.0002 Ciurczak, 1986, Determinationof particle size of pharmaceutical raw materials using near-infrared reflectance spectroscopy, Spectroscopy, 1, 36 Fukui, 2010, Determination of the crystallinity of cephalexin in pharmaceutical formulations by chemometrical near-infrared spectroscopy, Drug Dev. Ind. Pharm., 36, 72, 10.3109/03639040903092327 Aaltonen, 2003, Polymorph screening using near-infrared spectroscopy, Anal. Chem., 75, 5267, 10.1021/ac034205c Blanco, 2004, Characterization and analysis of polymorphs by near-infrared spectrometry, Anal. Chim. Acta, 502, 221, 10.1016/j.aca.2003.10.016 Blanco, 2004, Characterization and analysis of polymorphs by near-infrared spectrometry, Anal. Chim. Acta, 502, 221, 10.1016/j.aca.2003.10.016 Blanco, 2005, Application of NIR spectroscopy in polymorphic analysis study of pseudo-polymorphs stability, J. Pharm. Sci., 94, 1336, 10.1002/jps.20362 Chadha, 2015, Near-infrared spectroscopy: effective tool for screening of polymorphs in pharmaceuticals, Appl. Spectrosc. Rev., 50, 565, 10.1080/05704928.2015.1044663 Hu, 2013, Solid-state transformations of sulfathiazole polymorphs: the effects of milling and humidity, Cryst. Growth Des., 1, 3404, 10.1021/cg4002779 Kelly, 2012, Monitoring ibuprofen-nicotinamide cocrystal formation during solvent free continuous cocrystallization (SFCC) using near infrared spectroscopy as a PAT tool, Int. J. Pharm., 426, 15, 10.1016/j.ijpharm.2011.12.033 Wood, 2016, Near infrared spectroscopy as a multivariate process analytical tool for predicting pharmaceutical co-crystal concentration, J. Pharm. Biomed. Anal., 129, 172, 10.1016/j.jpba.2016.06.010 Kogermann, 2007, Qualitative in situ analysis of multiple solid-state forms using spectroscopy and partial least squares discriminant modeling, J. Pharm. Sci., 96, 1802, 10.1002/jps.20840 Wang, 2011, Polymorph transformation in paracetamol monitored by in-line NIR spectroscopy during a cooling crystallization process, AAPS PharmSciTech, 12, 764, 10.1208/s12249-011-9642-x Lee, 2015, In situ monitoring of antisolvent cocrystallization by combining near-infrared and Raman spectroscopies, Cryst. Growth Des., 15, 4385, 10.1021/acs.cgd.5b00700 Sarraguça, 2016, Real-time monitoring of cocrystallization processes by solvent evaporation: a near infrared study, Eur. J. Pharm. Sci., 90, 76, 10.1016/j.ejps.2015.12.025 Boiret, 2017, Use of near-infrared spectroscopy and multipoint measurements for quality control of pharmaceutical drug products, Anal. Bioanal. Chem., 409, 683, 10.1007/s00216-016-9756-9 Simon, 2015, Assessment of Recent Process Analytical Technology (PAT) Trends: A Multiauthor Review, Org. Process Res. Dev., 19, 3, 10.1021/op500261y Schönbichler, 2013, Comparison of NIR chemical imaging with conventional NIR, Raman and ATR-IR spectroscopy for quantification of furosemide crystal polymorphs in ternary powder mixtures, Eur. J. Pharm. Biopharm., 84, 616, 10.1016/j.ejpb.2013.01.006 da Silva, 2017, Portable near-infrared instruments: application for quality control of polymorphs in pharmaceutical raw materials and calibration transfer, J. Pharm. Biomed. Anal., 134, 287, 10.1016/j.jpba.2016.11.036 Taday, 2003, Using terahertz pulse spectroscopy to study the crystalline structure of a drug: a case study of the polymorphs of ranitidine hydrochloride, J. Pharm. Sci., 92, 831, 10.1002/jps.10358 Taday, 2004, Applications of terahertz spectroscopy to pharmaceutical sciences, Philos. Trans. R. Soc. Lond. A, 362, 351, 10.1098/rsta.2003.1321 Strachan, 2007, A theoretical and spectroscopic study of γ-crystalline and amorphous indometacin, J. Pharm. Pharmacol., 59, 261, 10.1211/jpp.59.2.0012 Strachan, 2005, Using terahertz pulsed spectroscopy to quantify pharmaceutical polymorphism and crystallinity, J. Pharm. Sci., 9, 837, 10.1002/jps.20281 Zeitler, 2005, Temperature dependent terahertz pulsed spectroscopy of carbamazepine, Thermochim. Acta, 436, 71, 10.1016/j.tca.2005.07.006 Yamaguchi, 2005, Terahertz absorption spectra of l-, d-, and dl-alanine and their application to determination of enantiometric composition, Appl. Phys. Lett., 86, 10.1063/1.1857080 Zeitler, 2007, Drug hydrate systems and dehydration processes studied by terahertz pulsed spectroscopy, Int. J. Pharm., 334, 78, 10.1016/j.ijpharm.2006.10.027 Li, 2012, Solid state characterizations and analysis of stability in azelnidipine polymorphs, Chem. Pharm. Bull., 60, 995, 10.1248/cpb.c12-00245 Charron, 2013, Chemical mapping of pharmaceutical cocrystals using terahertz spectroscopic imaging, Anal. Chem., 85, 1980, 10.1021/ac302852n Delaney, 2014, Conformational origins of polymorphism in two forms of flufenamic acid, J. Mol. Struct., 1078, 83, 10.1016/j.molstruc.2014.02.001 Tan, 2015, Probing phase transitions in simvastatin with terahertz time-domain spectroscopy, Mol. Pharm., 12, 810, 10.1021/mp500649q Zhang, 2016, Characteristics of low-frequency molecular phonon modes studied by THz spectroscopy and solid-state ab initio theory: polymorphs I and III of Diflunisal, J. Phys. Chem. B, 120, 1698, 10.1021/acs.jpcb.5b08798 Gala, 2014, Principles and applications of Raman spectroscopy in pharmaceutical drug discovery and development, Expert Opin. Drug Discovery, 10, 187, 10.1517/17460441.2015.981522 Smith, 2016, Investigating crystallinity using low frequency Raman spectroscopy: applications in pharmaceutical analysis, Spectroscopy, 31, 42 Févotte, 2007, In situ Raman spectroscopy for in-line control of pharmaceutical crystallization and solids elaboration processes: a review, Chem. Eng. Res. Des., 85, 906, 10.1205/cherd06229 Aina, 2010, Transmission Raman spectroscopy as a tool for quantifying polymorphic content of pharmaceutical formulations, Analyst, 135, 2328, 10.1039/c0an00352b Griffen, 2017, Recent advances in pharmaceutical analysis using transmission Raman spectroscopy, Spectroscopy, 32, 37 Gordon, 2011, Raman mapping of pharmaceuticals, Int. J. Pharm., 417, 151, 10.1016/j.ijpharm.2010.12.030 Vogt, 2013, Confocal UV and resonance Raman microscopic imaging of pharmaceutical products, Mol. Pharm., 10, 4216, 10.1021/mp400314s Kawata, 2017, Nano-Raman scattering microscopy: resolution and enhancement, Chem. Rev., 117, 4983, 10.1021/acs.chemrev.6b00560 Šašić, 2007, Raman mapping of low-content API pharmaceutical formulations. I. Mapping of alprazolam in alprazolam/Xanax tablets, Pharm. Res., 24, 58, 10.1007/s11095-006-9118-y Nie, 2016, Analytical approaches to investigate salt disproportionation in tablet matrices by Raman spectroscopy and Raman mapping, J. Pharm. Biomed. Anal., 118, 328, 10.1016/j.jpba.2015.10.024 Piqueras, 2014, Monitoring polymorphic transformations by using in situ Raman hyperspectral imaging and image multiset analysis, Anal. Chim. Acta, 819, 15, 10.1016/j.aca.2014.02.027 Wabuyele, 2017, Dispersive Raman spectroscopy for quantifying amorphous drug content in intact tablets, J. Pharm. Sci., 106, 579, 10.1016/j.xphs.2016.10.014 Dieringer, 2006, Surface enhanced Raman spectroscopy: new materials, concepts, characterization tools, and applications, Faraday Discuss., 132, 9, 10.1039/B513431P Pettinger, 2012, Tip-enhanced Raman spectroscopy: near-fields acting on a few molecules, Annu. Rev. Phys. Chem., 63, 379, 10.1146/annurev-physchem-032511-143807 Evans, 2008, Coherent anti-Stokes Raman scattering microscopy: chemical imaging for biology and medicine, Annu. Rev. Anal. Chem., 1, 883, 10.1146/annurev.anchem.1.031207.112754 Krafft, 2012, Raman and coherent anti-Stokes Raman scattering microspectroscopy for biomedical applications, J. Biomed. Opt., 17, 040801-1, 10.1117/1.JBO.17.4.040801 Sacré, 2014, Data processing of vibrational chemical imaging for pharmaceutical applications, J. Pharm. Biomed. Anal., 101, 123, 10.1016/j.jpba.2014.04.012 Cîntǎ-Pînzaru, 2004, Identification and characterization of pharmaceuticals using Raman and surface-enhanced Raman scattering, J. Raman Spectrosc., 35, 338, 10.1002/jrs.1153 Pavel, 2005, Raman, surface enhanced Raman spectroscopy, and DFT calculations: a powerful approach for the identification and characterization of 5-fluorouracil anticarcinogenic drug species, J. Phys. Chem. A, 109, 9945, 10.1021/jp053626q Panicker, 2010, FT-IR, FT-Raman, SERS spectra and computational calculations of 4-ethyl-N-(2′-hydroxy-5′-nitrophenyl)benzamide, J. Raman Spectrosc., 41, 381 Mary, 2012, FT-IR, FT-Raman, SERS and computational study of 5-ethylsulphonyl-2-(o-chlorobenzyl)benzoxazole, Spectrochim. Acta A Mol. Biomol. Spectrosc., 96, 617, 10.1016/j.saa.2012.07.006 Larkin, 2014, Polymorph Characterization of Active Pharmaceutical Ingredients (APIs) Using Low-Frequency Raman Spectroscopy, Appl. Spectrosc., 68, 758, 10.1366/13-07329 Hisada, 2015, Direct high-resolution imaging of crystalline components in pharmaceutical dosage forms using low-frequency Raman spectroscopy, Org. Process. Res. Dev., 19, 1796, 10.1021/acs.oprd.5b00329 Inoue, 2017, In situ monitoring of crystalline transformation of carbamazepine using probe-type low-frequency Raman spectroscopy, Org. Process. Res. Dev., 21, 262, 10.1021/acs.oprd.6b00329 Kolodziejski, 2011, Kinetics of 1H→13C NMR cross-polarization in polymorphs and solvates of the antipsychotic drug olanzapine, Solid State Nucl. Magn. Reson., 39, 41, 10.1016/j.ssnmr.2010.12.003 Wu, 1994, Spectral editing in CPMAS NMR. Generating subspectra based on proton multiplicities, J. Magn. Reson. A, 111, 29, 10.1006/jmra.1994.1222 Sangill, 1994, Optimized spectral editing of 13C MAS NMR spectra of rigid solids using cross-polarization method, J. Magn. Reson. A, 107, 67, 10.1006/jmra.1994.1048 Middleton, 1997, A cross-polarization magic-angle spinning 13C NMR characterization of the stable solid-state forms of cimetidine, J. Pharm. Sci., 86, 1400, 10.1021/js970139g Hu, 2000, Modified spectral editing methods for 13C CP/MAS experiments in solids, J. Magn. Reson., 142, 326, 10.1006/jmre.1999.1933 Charpentier, 2011, The PAW/GIPAW approach for computing NMR parameters: a new dimension added to NMR study of solids, Solid State Nucl. Magn. Reson., 40, 1, 10.1016/j.ssnmr.2011.04.006 Bühl, 2011, NMR spectroscopy: quantum-chemical calculations, WIREs Comput. Mol. Sci., 1, 634, 10.1002/wcms.63 Ashbrook, 2016, Combining solid-state NMR spectroscopy with first-principles calculations - a guide to NMR crystallography, Chem. Commun., 52, 7186, 10.1039/C6CC02542K Harris, 2007, Chemical shift computations on a crystallographic basis: some reflections and comments, Magn. Reson. Chem., 45, S174, 10.1002/mrc.2132 Küçükbenli, 2012, Complete 13C NMR chemical shifts assignment for cholesterol crystals by combined CP-MAS spectral editing and ab initio GIPAW calculations with dispersion forces, J. Phys. Chem. A, 116, 3765, 10.1021/jp3019974 Kolodziejski, 2000, 13C CP/MAS NMR study of a genistein/piperazine complex, Chem. Phys. Lett., 328, 263, 10.1016/S0009-2614(00)00930-1 Ueda, 1999, Hydrogen bonds in crystalline Imidazoles studied by 15N NMR and ab initio MO calculations, Z. Naturforsch., 54, 437, 10.1515/zna-1999-6-715 Kolodziejski, 2002, Kinetics of cross-polarization in solid-state NMR: a guide for chemists, Chem. Rev., 102, 613, 10.1021/cr000060n Antzutkin, 1995, Two-dimensional sideband separation in magic-angle-spinning NMR, J. Magn. Reson. A, 115, 7, 10.1006/jmra.1995.1142 Alderman, 1998, A sensitive, high resolution magic angle turning experiment for measuring chemical shift tensor principal values, Mol. Phys., 95, 1113, 10.1080/00268979809483243 Kalakewich, 2015, Monitoring the refinement of crystal structures with 15N solid-state NMR shift tensor data, J. Chem. Phys., 143, 194702-1, 10.1063/1.4935367 Bielecki, 1989, Frequency-switched pulse sequences: homonuclear decoupling and dilute spin NMR in solids, Chem. Phys. Lett., 155, 341, 10.1016/0009-2614(89)87166-0 Vinogradov, 1999, High-resolution proton solid-state NMR spectroscopy by phase-modulated Lee–Goldburg experiment, Chem. Phys. Lett., 314, 443, 10.1016/S0009-2614(99)01174-4 Sakellariou, 2000, Homonuclear dipolar decoupling in solid-state NMR using continuous phase modulation, Chem. Phys. Lett., 319, 253, 10.1016/S0009-2614(00)00127-5 Lesage, 2003, Experimental aspects of proton NMR spectroscopy in solids using phase-modulated homonuclear dipolar decoupling, J. Magn. Reson., 163, 105, 10.1016/S1090-7807(03)00104-6 Elena, 2004, Direct spectral optimisation of proton–proton homonuclear dipolar decoupling in solid-state NMR, Chem. Phys. Lett., 398, 532, 10.1016/j.cplett.2004.09.122 Brown, 2004, Probing proton−proton proximities in the solid state: high-resolution two-dimensional 1H−1H double-quantum CRAMPS NMR spectroscopy, J. Am. Chem. Soc., 126, 13230, 10.1021/ja045461p Ukmar, 2011, Solid-state NMR spectroscopy and first-principles calculations: a powerful combination of tools for the investigation of polymorphism of indomethacin, Acta Chim. Slov., 58, 425 Nishiyama, 2016, Fast magic-angle sample spinning solid-state NMR at 60–100kHz for natural abundance samples, Solid State Nucl. Magn. Reson., 78, 24, 10.1016/j.ssnmr.2016.06.002 Zhang, 2015, Selective excitation enables assignment of proton resonances and 1H-1H distance measurement in ultrafast magic angle spinning solid state NMR spectroscopy, J. Chem. Phys., 143, 034201-1 Zhang, 2017, Proton-based ultrafast magic angle spinning solid-state NMR spectroscopy, Acc. Chem. Res., 50, 1105, 10.1021/acs.accounts.7b00082 Zang, 2015, A novel high-resolution and sensitivity-enhanced three-dimensional solid-state NMR experiment under ultrafast MAS conditions, Sci Rep, 5, 11810-1 Zang, 2015, Proton-detected 3D 1H/13C/1H correlation experiment for structural analysis in rigid solids under ultrafast-MAS above 60kHz, J. Chem. Phys., 143, 164201-1 Wickramasinghe, 2015, Evolution of CPMAS under fast magic-angle-spinning at 100kHz and beyond, Solid State Nucl. Magn. Reson., 72, 9, 10.1016/j.ssnmr.2015.10.002 Ye, 2014, Rapid measurement of multidimensional 1H solid-state NMR spectra at ultra-fast MAS frequencies, J. Magn. Res., 239, 75, 10.1016/j.jmr.2013.12.010 Oikawa, 2017, Solid-state NMR meets electron diffraction: determination of crystalline polymorphs of small organic microcrystalline samples, Acta Crystallogr., C73, 219 Miah, 2017, 1H CSA parameters by ultrafast MAS NMR: measurement and applications to structure refinement, Solid State Nucl. Magn. Reson., 10.1016/j.ssnmr.2017.02.002 Miah, 2013, Measuring proton shift tensors with ultrafast MAS NMR, J. Magn. Reson., 235, 1, 10.1016/j.jmr.2013.07.005 Zhang, 2015, Proton chemical shift tensors determined by 3D ultrafast MAS double-quantum NMR spectroscopy, J. Chem. Phys., 143, 144201-1, 10.1063/1.4933114 Vijayan, 2009, Low-power solid-state NMR experiments for resonance assignment under fast magic-angle spinning, Chem. Phys. Chem., 10, 2205, 10.1002/cphc.200900439 Dannatt, 2015, 13C- and 1H-detection under fast MAS for the study of poorly available proteins: application to sub-milligram quantities of a 7 trans-membrane protein, J. Biomol. NMR, 62, 17, 10.1007/s10858-015-9911-1 Enright, 2007, The structure of two anhydrous polymorphs of caffeine from single-crystal diffraction and ultrahigh-field solid-state 13C NMR spectroscopy, Cryst. Growth Des., 7, 1406, 10.1021/cg070291o Rossini, 2012, Dynamic nuclear polarization NMR spectroscopy of microcrystalline solids, J. Am. Chem. Soc., 134, 16899, 10.1021/ja308135r Rossini, 2014, Dynamic Nuclear Polarization Enhanced NMR Spectroscopy for Pharmaceutical Formulations, J. Am. Chem. Soc., 136, 2324, 10.1021/ja4092038 Märker, 2015, A new tool for NMR crystallography: complete 13C/15N assignment of organic molecules at natural isotopic abundance using DNP-enhanced solid-state NMR, J. Am. Chem. Soc., 137, 13796, 10.1021/jacs.5b09964 Ni, 2013, High frequency dynamic nuclear polarization, Acc. Chem. Res., 2013, 1933, 10.1021/ar300348n Smith, 2016, Dynamic nuclear polarization as an enabling technology for solid state nuclear magnetic resonance spectroscopy, Anal. Chem., 88, 122, 10.1021/acs.analchem.5b04376 Pinon, 2015, Polymorphs of theophylline characterized by DNP enhanced solid-state NMR, Mol. Pharm., 12, 4146, 10.1021/acs.molpharmaceut.5b00610 Veinberg, 2016, Natural abundance 14N and 15N solid-state NMR of pharmaceuticals and their polymorphs, Phys. Chem. Chem. Phys., 18, 17713, 10.1039/C6CP02855A Brown, 2012, Applications of high-resolution 1H solid-state NMR, Solid State Nucl. Magn. Reson., 41, 1, 10.1016/j.ssnmr.2011.11.006 Mafra, 2009, High-resolution 1H homonuclear dipolar recoupling NMR spectra of biological solids at MAS rates up to 67kHz, J. Magn. Reson., 199, 111, 10.1016/j.jmr.2009.04.004 Fernandes, 2015, X-ray and NMR crystallography studies of novel theophylline cocrystals prepared by liquid assisted grinding, Cryst. Growth Des., 15, 3674, 10.1021/acs.cgd.5b00279 Widdifield, 2016, Furosemide's one little hydrogen atom: NMR crystallography structure verification of powdered molecular organics, Chem. Commun., 52, 6685, 10.1039/C6CC02171A Hamaed, 2008, Application of solid-state 35Cl NMR to the structural characterization of hydrochloride pharmaceuticals and their polymorphs, J. Am. Chem. Soc., 130, 11056, 10.1021/ja802486q Hildebrand, 2014, Cl-35 solid-state NMR of HCl salts of active pharmaceutical ingredients: structural prediction, spectral fingerprinting and polymorph recognition, CrystEngComm, 16, 7334, 10.1039/C4CE00544A Yates, 2004, Theoretical investigation of Oxygen-17 NMR shielding and electric field gradients in glutamic acid polymorphs, J. Phys. Chem. A, 108, 6032, 10.1021/jp049362+ Kong, 2013, Solid-state 17O NMR of pharmaceutical compounds: salicylic acid and aspirin, J. Phys. Chem. B, 117, 9643, 10.1021/jp405233f Vogt, 2013, 17O solid-state NMR as a sensitive probe of hydrogen bonding in crystalline and amorphous solid forms of diflunisal, Mol. Pharm., 10, 3433, 10.1021/mp400275w Tatton, 2012, Probing intermolecular interactions and nitrogen protonation in pharmaceuticals by novel 15N-edited and 2D 14N-1H solid-state NMR, CrystEngComm, 14, 2654, 10.1039/c2ce06547a Veinberg, 2015, Ultra-wideline 14N solid-state NMR as a method for differentiating polymorphs: glycine as a case study, CrystEngComm, 17, 5225, 10.1039/C5CE00060B Veinberg, 2016, 14N solid-state NMR of amino acids, Chem. Phys. Chem., 17, 4011, 10.1002/cphc.201600873 Reddy, 2016, Fast magic-angle spinning three-dimensional NMR experiment for simultaneously probing H—H and N—H proximities in solids, Anal. Chem., 88, 11412, 10.1021/acs.analchem.6b01869 Hughes, 2012, Exploiting in situ solid-state NMR for the discovery of new polymorphs during crystallization processes, J. Phys. Chem. Lett., 3, 3176, 10.1021/jz301252u Hughes, 2014, “CLASSIC NMR”: an in-situ NMR strategy for mapping the time-evolution of crystallization processes by combined liquid-state and solid-state measurements, Angew. Chem. Int. Ed., 53, 8939, 10.1002/anie.201404266 Harris, 2015, Monitoring the evolution of crystallization processes by in-situ solid-state NMR spectroscopy, Solid State Nucl. Magn. Reson., 65, 107, 10.1016/j.ssnmr.2014.11.004 Harris, 2017, NMR crystallization: in-situ NMR techniques for time-resolved monitoring of crystallization processes, Acta Cryst, C73, 137 Mandala, 2014, Monitoring cocrystal formation via in situ solid-state NMR, J. Phys. Chem. Lett., 5, 3340, 10.1021/jz501699h Paudel, 2014, Structural and dynamic properties of amorphous solid dispersions: the role of solid-state nuclear magnetic resonance spectroscopy and relaxometry, J. Pharm. Sci., 103, 2635, 10.1002/jps.23966 Moran, 2017, Exploiting NMR spectroscopy for the study of disorder in solids, Int. Rev. Phys. Chem., 36, 39, 10.1080/0144235X.2017.1256604 Nishiyama, 2010, 13C solid-state NMR chromatography by magic angle spinning 1H T1 relaxation ordered spectroscopy, J. Magn. Reson., 202, 135, 10.1016/j.jmr.2009.10.009 Mantle, 2011, Quantitative magnetic resonance micro-imaging methods for pharmaceutical research, Int. J. Pharm., 417, 173, 10.1016/j.ijpharm.2010.11.035 Schumacher, 2017, Time domain NMR as a new process monitoring method for characterization of pharmaceutical hydrates, J. Pharm. Biomed., 137, 96, 10.1016/j.jpba.2017.01.017 Ripmeester, 2013, NMR crystallography, CrystEngComm, 15, 8598, 10.1039/c3ce90151c Chierotti, 2013, NMR crystallography: the use of dipolar interactions in polymorph and co-crystal investigation, CrystEngComm, 15, 8599, 10.1039/c3ce41026a Pindelska, 2015, Crystal structures of tiotropium bromide and its monohydrate in view of combined solid-state nuclear magnetic resonance and gauge-including projector-augmented wave studies, J. Pharm. Sci., 104, 2285, 10.1002/jps.24490 Pindelska, 2015, Solid-state NMR as an effective method of polymorphic analysis: solid dosage forms of clopidogrel hydrogensulfate, J. Pharm. Sci., 104, 106, 10.1002/jps.24249 Pindelska, 2016, Alkyl spacer length and protonation induced changes in crystalline psychoactive arylpiperazine derivatives: single-crystal X-ray, solid-state NMR, and computational studies, Cryst. Growth Des., 16, 6371, 10.1021/acs.cgd.6b00993 Sokal, 2017, Pharmaceutical properties of two ethenzamide-gentisic acid cocrystal polymorphs: drug release profiles, spectroscopic studies and theoretical calculations, Int. J. Pharm., 522, 80, 10.1016/j.ijpharm.2017.03.004 Burgess, 2012, Sodium-23 solid-state nuclear magnetic resonance of commercial sodium naproxen and its solvates, J. Pharm. Sci., 101, 2930, 10.1002/jps.23196 Haines, 2012 Höhne, 1996, Theoretical fundamentals of differential scanning calorimeters, 21 Danley, 2002, New heat flux DSC measurement technique, Thermochim. Acta, 395, 201, 10.1016/S0040-6031(02)00212-5 Tanaka, 1992, Theory of power-compensated DSC, Thermochim. Acta, 210, 67, 10.1016/0040-6031(92)80277-4 Verdonck, 1999, A discussion of the principles and applications of modulated temperature DSC (MTDSC), Int. J. Pharm., 192, 3, 10.1016/S0378-5173(99)00267-7 Gramaglia, 2005, High speed DSC (hyper-DSC) as a tool to measure the solubility of a drug within a solid or semi-solid matrix, Int. J. Pharm., 301, 1, 10.1016/j.ijpharm.2005.04.038 Liu, 2009, Starch gelatinization under pressure studied by high pressure DSC, Carbohydr. Polym., 7, 395, 10.1016/j.carbpol.2008.07.034 Chadha, 2017, Cocrystals of hesperetin: structural, pharmacokinetic, and Pharmacodynamic evaluation, Cryst. Growth Des., 17, 2386, 10.1021/acs.cgd.6b01769 Knopp, 2016, Recent advances and potential applications of modulated differential scanning calorimetry (mDSC) in drug development, Eur. J. Pharm. Sci., 87, 164, 10.1016/j.ejps.2015.12.024 Skotnicki, 2015, Bisoprolol and bisoprolol-valsartan compatibility studied by differential scanning calorimetry, nuclear magnetic resonance and X-ray powder diffractometry, Pharm. Res., 32, 414, 10.1007/s11095-014-1471-7 Chadha, 2014, Drug–excipient compatibility screening—role of thermoanalytical and spectroscopic techniques, J. Pharm. Biomed. Anal., 87, 82, 10.1016/j.jpba.2013.06.016 Saklatvala, 2005, J. Drug Deliv. Sci. Technol., 15, 257, 10.1016/S1773-2247(05)50046-7 Gabbott, 2003, A high-sensitivity, high-speed DSC technique: measurement of amorphous lactose, Am. Lab., 35, 17 McGregor, 2008, The use of high-speed differential scanning calorimetry (Hyper-DSC™) in the study of pharmaceutical polymorphs, Int. J. Pharm., 350, 48, 10.1016/j.ijpharm.2007.08.015 Ford, 2012, Fast-scan DSC and its role in pharmaceutical physical form characterisation and selection, Adv. Drug Deliv. Rev., 64, 422, 10.1016/j.addr.2011.12.001 Carvalho, 2016, Rare case of polymorphism in a racemic fluoxetine nitrate salt: phase behavior and relative stability, Cryst. Growth Des., 16, 3875, 10.1021/acs.cgd.6b00442 Gabbott, 2008 Menczel, 2009, Thermogravimetric analysis (TGA), 241 Erlich, 1989, Acyclovir-resistant herpes simplex virus infections in patients with the acquired immunodeficiency syndrome, N. Engl. J. Med., 320, 293, 10.1056/NEJM198902023200506 Bruni, 2013, Preparation and physicochemical characterization of acyclovir cocrystals with improved dissolution properties, J. Pharm. Sci., 102, 4079, 10.1002/jps.23721 Sarkar, 2015, Cocrystals of acyclovir with promising physicochemical properties, J. Pharm. Sci., 104, 98, 10.1002/jps.24248 Diniz, 2017, Reducing the hygroscopicity of the anti-tuberculosis drug (S, S)-ethambutol using multicomponent crystal forms, Cryst. Growth Des., 17, 2622, 10.1021/acs.cgd.7b00144 Carvalho, 2016, Reversible solid-state hydration/dehydration of paroxetine HBr hemihydrate: structural and thermochemical studies, Cryst. Growth Des., 16, 1543, 10.1021/acs.cgd.5b01672 Šimek, 2016, Hot-stage microscopy for determination of API fragmentation: comparison with other methods, Pharm. Dev. Technol., 21, 583, 10.3109/10837450.2015.1026608 Lin, 2012, The use of hot-stage microscopy and thermal micro-Raman spectroscopy in the study of phase transformation of metoclopramide HCl monohydrate, J. Raman Spectrosc., 43, 1166, 10.1002/jrs.3155 Berry, 2008, Applying hot-stage microscopy to co-crystal screening: a study of nicotinamide with seven active pharmaceutical ingredients, Cryst. Growth Des., 8, 1697, 10.1021/cg800035w Kuminek, 2016, Cocrystals to facilitate delivery of poorly soluble compounds beyond-rule-of-5, Adv. Drug Deliv. Rev., 101, 143, 10.1016/j.addr.2016.04.022 Thakuria, 2013, Pharmaceutical cocrystals and poorly soluble drugs, Int. J. Pharm., 45, 101, 10.1016/j.ijpharm.2012.10.043 Good, 2009, Solubility advantage of pharmaceutical cocrystal, Cryst. Growth Des., 9, 2252, 10.1021/cg801039j Lawrence, 2004, Feasibility studies of utilizing disk intrinsic dissolution rate to classify drugs, Int. J. Pharm., 27, 221 Zakeri-Milani, 2009, Biopharmaceutical classification of drugs using intrinsic dissolution rate (IDR) and rat intestinal permeability, Eur. J. Pharm. Biopharm., 73, 102, 10.1016/j.ejpb.2009.04.015 Kesisoglou, 2008, Understanding the effect of API properties on bioavailability through absorption modeling, AAPS J., 10, 516, 10.1208/s12248-008-9061-4 Baka, 2008, Study of equilibrium solubility measurement by saturation shake-flask method using hydrochlorothiazide as model compound, J. Pharm. Biomed. Anal., 46, 335, 10.1016/j.jpba.2007.10.030 Zeng, 2017, Structural characterization and dissolution profile of mycophenolic acid cocrystals, Eur. J. Pharm. Sci., 102, 140, 10.1016/j.ejps.2017.02.035 Mitsui, 1969, Immunosuppressive effect of mycophenolic acid, J. Antibiot., 22, 358, 10.7164/antibiotics.22.358 Carter, 1969, Mycophenolic acid: an anti-cancer compound with unusual properties, Nature, 223, 848, 10.1038/223848a0 Lidgate, 2002, Influence of ferrous sulfate on the solubility, partition coefficient, and stability of mycophenolic acid and the ester mycophenolate mofetil, Drug Dev. Ind. Pharm., 28, 1275, 10.1081/DDC-120015361 Pitts, 1950, Mechanism of action and therapeutic use of diuretics, Pharmacol. Rev., 2, 161 Prandota, 2002, Furosemide: progress in understanding its diuretic, anti-inflammatory, and bronchodilating mechanism of action, and use in the treatment of respiratory tract diseases, Am. J. Therapeut., 9, 317, 10.1097/00045391-200207000-00009 Matsuda, 1990, Physicochemical characterization of furosemide modifications, Int. J. Pharm., 60, 11, 10.1016/0378-5173(90)90185-7 Ueto, 2011, Polymorphs and a hydrate of furosemide–nicotinamide 1: 1 cocrystal, Cryst. Growth Des., 12, 485, 10.1021/cg2013232 Goud, 2012, Novel furosemide cocrystals and selection of high solubility drug forms, J. Pharm. Sci., 101, 664, 10.1002/jps.22805 Higuchi, 1965, Phase-solubility techniques, Adv. Anal. Chem. Instrum., 4, 117 Khandavilli, 2014, High solubility crystalline hydrates of Na and K furosemide salts, CrystEngComm, 16, 4842, 10.1039/C3CE42347F Sayer, 2013, New horizons in the pathogenesis, diagnosis and management of sarcopenia, Age Ageing, 42, 145, 10.1093/ageing/afs191 Deng, 2017, Evaluation of a biphasic in vitro dissolution test for estimating the bioavailability of carbamazepine polymorphic forms, Eur. J. Pharm. Sci., 105, 64, 10.1016/j.ejps.2017.05.013 Tomson, 2015, Vol. 4, 431 Grzesiak, 2003, Comparison of the four anhydrous polymorphs of carbamazepine and the crystal structure of form I, J. Pharm. Sci., 92, 2260, 10.1002/jps.10455 Harris, 2005, Structural studies of the polymorphs of carbamazepine, its dihydrate, and two solvates, Org. Process. Res. Dev., 9, 902, 10.1021/op0500990 Vangani, 2009, Dissolution of poorly water-soluble drugs in biphasic2 media using USP 4 and fiber optic system, Clin. Res. Regul. Aff., 26, 8, 10.1080/10601330902905887 Yuksel, 2000, Comparison of in vitro dissolution profiles by Anova-based, model-dependent and-independent methods, Int. J. Pharm., 209, 57, 10.1016/S0378-5173(00)00554-8 Costa, 2001, Modeling and comparison of dissolution profiles, Eur. J. Pharm. Sci., 13, 123, 10.1016/S0928-0987(01)00095-1 Saranadasa, 2001, Defining similarity of dissolution profiles: through Hotelling's T2 statistic, Pharma. Technol., 25, 46 Sathe, 1996, In-vitro dissolution profile comparison: statistics and analysis, model dependent approach, Pharm. Res., 13, 1799, 10.1023/A:1016020822093 Ruiz, 2014, Biopharmaceutical relevance of dissolution profile comparison: proposal of a combined approach, Dissolut. Technol., 21, 32, 10.14227/DT210114P32 Baertschi, 2011 Loftsson, 2014 Blaschko, 1937, The oxidation of adrenaline and other amines, Biochem. J., 31, 2187, 10.1042/bj0312187 Yoshioka, 2016 Chemburkar, 2002, Dealing with the impact of ritonavir polymorphs on the late stages of bulk drug process development, Org. Process. Res. Dev., 4, 413, 10.1021/op000023y Behera, 2011, Method development, validation and stability study of ritonavir in bulk and pharmaceutical dosage form by spectrophotometric method, Chron. Young Sci., 2, 161, 10.4103/2229-5186.90894 Bolla, 2014, Celecoxib cocrystal polymorphs with cyclic amides: synthons of a sulfonamide drug with carboxamide coformers, CrystEngComm, 16, 24, 10.1039/C3CE41885E Thorat, 2015, Solid-state phase transformations and storage stability of curcumin polymorphs, Cryst. Growth Des., 15, 1757, 10.1021/cg501814q Young, 2007, The use of organic vapor sorption to determine low levels of amorphous content in processed pharmaceutical powders, Drug Dev. Ind. Pharm., 33, 91, 10.1080/03639040600969991 Sheokand, 2014, Dynamic vapor sorption as a tool for characterization and quantification of amorphous content in predominantly crystalline materials, J. Pharm. Sci., 103, 3364, 10.1002/jps.24160 Rudy, 2017, Comparison of the saturated salt solution and the dynamic vapor sorption techniques based on the measured sorption isotherm of barley straw, Constr. Build. Mater., 141, 140, 10.1016/j.conbuildmat.2017.03.005 Ferrannini, 2010, Dapagliflozin monotherapy in type 2 diabetic patients with inadequate glycemic control by diet and exercise, Diabetes Care, 33, 2217, 10.2337/dc10-0612 Tereshchenko, 2005, Deliquescence: hygroscopicity of water-soluble crystalline solids, J. Pharm. Sci., 104, 3639, 10.1002/jps.24589 Deshpande, 2008, Crystal structures of sglt2 inhibitors and processes for preparing same Deng, 2017, Dapagliflozin-citric acid cocrystal showing better solid state properties than dapagliflozin, Eur. J. Pharm. Sci., 104, 255, 10.1016/j.ejps.2017.04.008 Lin, 2016, Mechanochemical approaches to pharmaceutical cocrystal formation and stability analysis, Curr. Pharm. Des., 22, 5001, 10.2174/1381612822666160726111253 Lefebvre, 1986, Polymorphic transitions of carbamazepine during grinding and compression, Drug Dev. Ind. Pharm., 12, 1913, 10.3109/03639048609042617 Vitez, 1988, The evolution of hot-stage microscopy to aid solid-state characterizations of pharmaceutical solids, Thermochem. Acta, 324, 187, 10.1016/S0040-6031(98)00535-8 Wang, 2011, A continuous process for solid-state dehydration, amorphization and recrystallization of metoclopramide HCL monohydrate studied by simultaneous DSC-FTIR microspectroscopy, J. Therm. Anal. Calorim., 104, 261, 10.1007/s10973-010-0998-z Cheng, 2011, Thermal FT-IR microspectroscopy for rapid detection of solid-state ion-exchange reaction between metoclopramide HCl monohydrate and potassium bromide, Analyst, 136, 1036, 10.1039/C0AN00570C Qiu, 2005, Kinetic study of the Maillard reaction between metoclopramide hydrochloride and lactose, Int. J. Pharm., 303, 20, 10.1016/j.ijpharm.2005.06.016 Mannhold, 2009 Agoram, 2001, Predicting the impact of physiological and biochemical processes on oral drug bioavailability, Adv. Drug Deliv. Rev., 50, S41, 10.1016/S0169-409X(01)00179-X Chan, 1996, Physicochemical and drug-delivery considerations for oral drug bioavailability, Drug Discov. Today, 1, 461, 10.1016/1359-6446(96)10039-8 Amidon, 1995, A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability, Pharm. Res., 12, 413, 10.1023/A:1016212804288 Musther, 2014, Animal versus human oral drug bioavailability: do they correlate?, Eur. J. Pharm. Sci., 57, 280, 10.1016/j.ejps.2013.08.018 Shah, 1992, Analytical methods validation: bioavailability, bioequivalence, and pharmacokinetic studies, J. Pharm. Sci., 81, 309, 10.1002/jps.2600810324 Huang, 2014, Baicalein–nicotinamide cocrystal with enhanced solubility, dissolution, and oral bioavailability, J. Pharm. Sci., 103, 2330, 10.1002/jps.24048 Miocinovis, 2005, In vivo and in vitro effect of baicalein on human prostate cancer cells, Int. J. Oncol., 26, 241 Shao, 2002, Baicalein attenuates oxidant stress in cardiomyocytes, Am. J. Physiol. Heart Circ. Physiol., 282, H999, 10.1152/ajpheart.00163.2001 Kubo, 1981, Studies on Scutellariae radix. II. The antibacterial substance, Planta Med., 43, 194, 10.1055/s-2007-971499 Zhang, 2011, Enhanced bioavailability after oral and pulmonary administration of baicalein nanocrystal, Int. J. Pharm., 420, 180, 10.1016/j.ijpharm.2011.08.023 Obach, 1997, The prediction of human pharmacokinetic parameters from preclinical and in vitro metabolism data, J. Pharmacol. Exp. Therapeut., 283, 46 Nestorov, 2003, Whole body pharmacokinetic models, Clin. Pharmacokinet., 42, 883, 10.2165/00003088-200342100-00002 Rowland, 2011, Physiologically-based pharmacokinetics in drug development and regulatory science, Annu. Rev. Pharmacol. Toxicol., 51, 45, 10.1146/annurev-pharmtox-010510-100540 Grass, 2002, Physiologically-based pharmacokinetic simulation modelling, Adv. Drug Deliv. Rev., 54, 433, 10.1016/S0169-409X(02)00013-3 Olivares-Morales, 2016, Development of a novel simplified PBPK absorption model to explain the higher relative bioavailability of the OROS® formulation of oxybutynin, AAPS J., 18, 1532, 10.1208/s12248-016-9965-3 Pratt, 2017, Pharmacokinetics of ferric pyrophosphate citrate, a novel iron salt, administered intravenously to healthy volunteers, J. Clin. Pharmacol., 57, 312, 10.1002/jcph.819 Wedemeyer, 2014, Pharmacokinetic drug interaction profiles of proton pump inhibitors: an update, Drug Saf., 37, 201, 10.1007/s40264-014-0144-0 Zhang, 2004, Phase transformation considerations during process development and manufacture of solid oral dosage forms, Adv. Drug Deliv. Rev., 56, 371, 10.1016/j.addr.2003.10.009 Hilfiker, 2006 Good, 2016, 1 Pacilio, 2014, High-resolution solid-state NMR spectroscopy: characterization of polymorphism in cimetidine, a pharmaceutical compound, J. Chem. Educ., 91, 1236, 10.1021/ed400353w Ullah, 2016, The development of carbamazepine-succinic acid cocrystal tablet formulations with improved in vitro and in vivo performance, Drug Dev. Ind. Pharm., 42, 969, 10.3109/03639045.2015.1096281 Zhou, 2016, Resveratrol cocrystals with enhanced solubility and tabletability, Int. J. Pharm., 509, 391, 10.1016/j.ijpharm.2016.06.006 Chang, 2017, Superior plasticity and tabletability of theophylline monohydrate, Mol. Pharm., 14, 2047, 10.1021/acs.molpharmaceut.7b00124 Khomane, 2013, Molecular understanding of the compaction behavior of indomethacin polymorphs, Mol. Pharm., 10, 631, 10.1021/mp300390m Krishna, 2015, Correlation among crystal structure, mechanical behavior, and tabletability in the co-crystals of vanillin isomers, Cryst. Growth Des., 15, 1827, 10.1021/cg5018642 Gharaibeh, 2011, Mechanical energies associated with compaction of form I and form II paracetamol powder, Powder Technol., 214, 161, 10.1016/j.powtec.2011.08.008 Karki, 2009, Improving mechanical properties of crystalline solids by cocrystal formation: new compressible forms of paracetamol, Adv. Mater., 21, 3905, 10.1002/adma.200900533 Elbagerma, 2011, Identification of a new cocrystal of citric acid and paracetamol of pharmaceutical relevance, CrystEngComm, 13, 1877, 10.1039/C0CE00461H Hiendrawan, 2016, Physicochemical and mechanical properties of paracetamol cocrystal with 5-nitroisophthalic acid, Int. J. Pharm., 497, 106, 10.1016/j.ijpharm.2015.12.001 Pisklak, 2016, 13C solid-state NMR analysis of the most common pharmaceutical excipients used in solid drug formulations, part I: chemical shifts assignment, J. Pharm. Biomed. Anal., 122, 81, 10.1016/j.jpba.2016.01.032 Morott, 2015, The effects of screw configuration and polymeric carriers on hot-melt extruded taste-masked formulations incorporated into orally disintegrating tablets, J. Pharm. Sci., 104, 124, 10.1002/jps.24262 Maeno, 2014, Novel pharmaceutical cocrystal consisting of paracetamol and trimethylglycine, a new promising cocrystal former, Int. J. Pharm., 473, 179, 10.1016/j.ijpharm.2014.07.008 Yi, 2014, Preparation of sildenafil citrate microcapsules and in vitro/in vivo evaluation of taste masking efficiency, Int. J. Pharm., 466, 286, 10.1016/j.ijpharm.2014.03.001 Ayenew, 2009, Trends in pharmaceutical taste masking technologies: a patent review, Recent Pat. Drug Deliv. Formul., 3, 26, 10.2174/187221109787158364 Wang, 2016, In vitro and in vivo anti-tumor efficacy of 10-hydroxycamptothecin polymorphic nanoparticle dispersions: shape-and polymorph-dependent cytotoxicity and delivery of 10-hydroxycamptothecin to cancer cells, Nanomedicine, 12, 881, 10.1016/j.nano.2015.12.373 Huang, 2015, New polymorphs of 9-nitro-camptothecin prepared using a supercritical anti-solvent process, Int. J. Pharm., 496, 551, 10.1016/j.ijpharm.2015.10.079 Gopi, 2016, New cocrystals of hydrochlorothiazide: optimizing solubility and membrane diffusivity, Cryst. Growth Des., 17, 308, 10.1021/acs.cgd.6b01540 Raza, 2017, Aceclofenac polymorphs: preparation, characterization and intestinal permeation studies, J. Drug Deliv. Sci. Technol., 39, 69, 10.1016/j.jddst.2017.03.004 Furuta, 2015, Physicochemical and crystal structure analysis of pranlukast pseudo-polymorphs II: solvate and cocrystal, J. Pharm. Biomed. Anal., 111, 44, 10.1016/j.jpba.2015.03.008