Pharmaceutical cocrystals, salts and polymorphs: Advanced characterization techniques
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
