Advertisement

Pharmaceutical Terahertz Spectroscopy and Imaging

  • J. Axel ZeitlerEmail author
Chapter
Part of the Advances in Delivery Science and Technology book series (ADST)

Abstract

Terahertz spectroscopy and imaging have developed rapidly over the past decade as versatile analytical tools for the characterisation of drug delivery systems. In this chapter the technology that has enabled the recent surge of interest in using terahertz techniques is explained in terms of its basic principles and the specific implementations of pharmaceutical relevance. Using a number of examples and case studies an overview of the current state-of-the-art applications of terahertz radiation in pharmaceutics is presented. In the field of spectroscopy this ranges from polymorph detection and quantification, detailed analysis of phase transitions to amorphous stability. Important imaging applications include non-destructive coating thickness measurements, characterisation of the microstructure of tablet matrices as well as liquid transport into tablets during disintegration.

Keywords

Terahertz spectroscopy Terahertz imaging Polymorph detection Solid-state properties Phase transition Amorphous Crystallinity Amorphous stability Crystallisation Film coating Tablet porosity Tablet hardness Disintegration testing 

References

  1. Ajito K, Kim JY, Ueno Y, Song HJ, Ueda K, Limwikrant W, Yamamoto K, Moribe K (2014) Nondestructive multicomponent terahertz chemical imaging of medicine in tablets. J Electrochem Soc 161(9):B171–B175. doi: 10.1149/2.0201409jes CrossRefGoogle Scholar
  2. Allis DG, Prokhorova D, Korter T (2006) Solid-state modeling of the terahertz spectrum of the high explosive HMX. J Phys Chem A 110(5):1951–1959PubMedCrossRefGoogle Scholar
  3. Angell CA, Ngai KL, McKenna GB, McMillan PF, Martin SW (2000) Relaxation in glassforming liquids and amorphous solids. J Appl Phys 88(6):3113–3157. doi: 10.1063/1.1286035 CrossRefGoogle Scholar
  4. Auston D (1975) Picosecond optoelectronic switching and gating in silicon. Appl Phys Lett 26(3):101–103CrossRefGoogle Scholar
  5. Bawuah P, Pierotic Mendia A, Silfsten P, Pääkkönen P, Ervasti T, Ketolainen J, Zeitler JA, Peiponen KE (2014a) Detection of porosity of pharmaceutical compacts by terahertz radiation transmission and light reflection measurement techniques. Int J Pharm 465(1–2):70–76. doi: 10.1016/j.ijpharm.2014.02.011 PubMedCrossRefGoogle Scholar
  6. Bawuah P, Silfsten P, Ervasti T, Ketolainen J, Zeitler JA, Peiponen KE (2014b) Non-contact weight measurement of flat-faced pharmaceutical tablets using terahertz transmission pulse delay measurements. Int J Pharm 476(1–2):16–22. doi: 10.1016/j.ijpharm.2014.09.027 PubMedCrossRefGoogle Scholar
  7. Bernstein J (2007) Polymorphism in molecular crystals. Oxford University Press, OxfordCrossRefGoogle Scholar
  8. Bhattacharya S, Suryanarayanan R (2009) Local mobility in amorphous pharmaceuticals-characterization and implications on stability. J Pharm Sci 98(9):2935–2953. doi: 10.1002/jps.21728 PubMedCrossRefGoogle Scholar
  9. Brock D, Zeitler JA, Funke A, Knop K, Kleinebudde P (2012) A comparison of quality control methods for active coating processes. Int J Pharm 439:289–295. doi: 10.1016/j.ijpharm.2012.09.021 PubMedCrossRefGoogle Scholar
  10. Brock D, Zeitler JA, Funke A, Knop K, Kleinebudde P (2013a) Critical factors in the measurement of tablet film coatings using terahertz pulsed imaging 102(6):1813–1824. doi:  10.1002/jps.23521
  11. Brock D, Zeitler JA, Funke A, Knop K, Kleinebudde P (2013b) Evaluation of critical process parameters for intra-tablet coating uniformity using terahertz pulsed imaging. Eur J Pharm Biopharm 85(3 Pt B):1122–1129. doi: 10.1016/j.ejpb.2013.07.004
  12. Brock D, Zeitler JA, Funke A, Knop K, Kleinebudde P (2014) Evaluation of critical process parameters for inter-tablet coating uniformity of active-coated GITS using Terahertz Pulsed Imaging. Eur J Pharm Biopharm 88:434–442. doi: 10.1016/j.ejpb.2014.06.016 PubMedCrossRefGoogle Scholar
  13. Bründermann E, Hübers HW, Kimmitt MF (2012) Terahertz techniques. Springer, HeidelbergCrossRefGoogle Scholar
  14. Burnett AD, Kendrick J, Russell C, Christensen J, Cunningham JE, Pearson AR, Linfield EH, Davies AG (2013) Effect of molecular size and particle shape on the terahertz absorption of a homologous series of tetraalkylammonium salts. Anal Chem 85(16):7926–7934. doi: 10.1021/ac401657r PubMedCrossRefGoogle Scholar
  15. Capaccioli S, Ngai KL, Thayyil MS, Prevosto D (2015) Coupling of caged molecule dynamics to JG β-relaxation: I. J Phys Chem B 119(28):8800–8808. doi: 10.1021/acs.jpcb.5b04408 PubMedCrossRefGoogle Scholar
  16. Chantry GW (1971) Submillimetre spectroscopy: guide to the theoretical and experimental physics of the infrared, 1st edn. Academic, New YorkGoogle Scholar
  17. Charron DM, Ajito K, Kim JY, Ueno Y (2013) Chemical mapping of pharmaceutical cocrystals using terahertz spectroscopic imaging. Anal Chem 85(4):1980–1984. doi: 10.1021/ac302852n PubMedCrossRefGoogle Scholar
  18. Chen Y, Ma Y, Lu Z, Peng B, Chen Q (2011) Quantitative analysis of terahertz spectra for illicit drugs using adaptive-range micro-genetic algorithm. J Appl Phys 110(4):044902. doi: 10.1063/1.3624737 CrossRefGoogle Scholar
  19. Cogdill R, Short S, Forcht R, Shi Z, Shen Y, Taday PF, Anderson CA, Drennen J (2006) An efficient method-development strategy for quantitative chemical imaging using terahertz puls spectroscopy. J Pharm Innov 1(1):63–75CrossRefGoogle Scholar
  20. Darkwah J, Smith G, Ermolina I, Mueller-Holtz M (2013) A THz spectroscopy method for quantifying the degree of crystallinity in freeze-dried gelatin/amino acid mixtures: an application for the development of rapidly disintegrating tablets. Int J Pharm 455(1–2):357–364. doi: 10.1016/j.ijpharm.2013.06.073 PubMedCrossRefGoogle Scholar
  21. Day GM, Zeitler JA, Jones W, Rades T, Taday PF (2006) Understanding the influence of polymorphism on phonon spectra: lattice dynamics calculations and terahertz spectroscopy of carbamazepine. J Phys Chem B 110(1):447–456. doi: 10.1021/jp055439y PubMedCrossRefGoogle Scholar
  22. Dees PJ (1980) The mechanism of tablet disintegration. PhD thesis, LeidenGoogle Scholar
  23. Delaney SP, Pan D, Galella M, Yin SX, Korter TM (2012) Understanding the origins of conformational disorder in the crystalline polymorphs of Irbesartan. Cryst Growth Des 12(10):5017–5024. doi: 10.1021/cg300977e CrossRefGoogle Scholar
  24. Delaney SP, Pan D, Yin SX, Smith TM, Korter TM (2013a) Evaluating the roles of conformational strain and cohesive binding in crystalline polymorphs of aripiprazole. Cryst Growth Des 13(7):2943–2952. doi: 10.1021/cg400358e CrossRefGoogle Scholar
  25. Delaney SP, Smith TM, Korter TM (2013b) Conformation versus cohesion in the relative stabilities of gabapentin polymorphs. RSC Adv 4(2):855. doi: 10.1039/c3ra43887b CrossRefGoogle Scholar
  26. Dexheimer SL (2007b) Terahertz spectroscopy. Principles and applications. CRC Press, Boca RatonCrossRefGoogle Scholar
  27. Dobroiu A, Sasaki Y, Shibuya T, Otani C, Kawase K (2007) THz-wave spectroscopy applied to the detection of illicit drugs in mail. Proc IEEE 95(8):1566–1575CrossRefGoogle Scholar
  28. Du Y, Xia Y, Zhang H, Hong Z (2013) Using terahertz time-domain spectroscopical technique to monitor cocrystal formation between piracetam and 2,5-dihydroxybenzoic acid. Spectrochim Acta A Mol Biomol Spectrosc 111(C):192–195. doi: 10.1016/j.saa.2013.03.081 PubMedCrossRefGoogle Scholar
  29. Ebbinghaus S, Meister K, Born B (2010) Antifreeze glycoprotein activity correlates with long-range protein-water dynamics. J Am Chem Soc 132(35):12210–12211PubMedCrossRefGoogle Scholar
  30. El Haddad J, de Miollis F, Sleiman JB, Canioni L, Mounaix P, Bousquet B (2014) Chemometrics applied to quantitative analysis of ternary mixtures by terahertz spectroscopy. Anal Chem 86(10):4927–4933. doi: 10.1021/ac500253b PubMedCrossRefGoogle Scholar
  31. Ervasti T, Silfsten P, Ketolainen J, Peiponen KE (2011) A study on the resolution of a terahertz spectrometer for the assessment of the porosity of pharmaceutical tablets. Appl Spectrosc 66(3):319–323. doi: 10.1366/11-06315 CrossRefGoogle Scholar
  32. Ermolina I, Darkwah J, Smith G (2014) Characterisation of crystalline-amorphous blends of sucrose with terahertz-pulsed spectroscopy: the development of a prediction technique for estimating the degree of crystallinity with partial least squares regression. AAPS PharmSciTech 15(2):253–260Google Scholar
  33. Falconer RJ, Markelz AG (2012) Terahertz spectroscopic analysis of peptides and proteins. J Infrared Millim Terahertz Waves 33(10):973–988. doi: 10.1007/s10762-012-9915-9 CrossRefGoogle Scholar
  34. Fattinger C, Grischkowsky DR (1989) Terahertz beams. Appl Phys Lett 54(6):490–492CrossRefGoogle Scholar
  35. Fischer B, Walther M, Jepsen PU (2002) Far-infrared vibrational modes of DNA components studied by terahertz time-domain spectroscopy. Phys Med Biol 47(21):3807–3814. doi: 10.1088/0031-9155/47/21/319 PubMedCrossRefGoogle Scholar
  36. Fitzgerald A, Cole B, Taday PF (2005) Nondestructive analysis of tablet coating thicknesses using terahertz pulsed imaging. J Pharm Sci 94(1):177–183. doi: 10.1002/jps.20225 PubMedCrossRefGoogle Scholar
  37. Freireich B, Kumar R, Ketterhagen W, Su K, Wassgren C, Zeitler JA (2015) Comparisons of intra-tablet coating variability using DEM simulations, asymptotic limit models, and experiments. Chem Eng Sci 131:197–212. doi: 10.1016/j.ces.2015.03.013 CrossRefGoogle Scholar
  38. Gebbie HA (1984) Fourier transform spectroscopy—recollections of the period 1955–1960. Infrared Phys 24(2–3):105–109. doi: 10.1016/0020-0891(84)90056-3 CrossRefGoogle Scholar
  39. Gendre C, Genty M, Boiret M, Julien M, Meunier L, Lecoq O, Baron M, Chaminade P, Péan JM (2011) Development of a Process Analytical Technology (PAT) for in-line monitoring of film thickness and mass of coating materials during a pan coating operation. Eur J Pharm Sci 43(4):244–250. doi: 10.1016/j.ejps.2011.04.017 PubMedCrossRefGoogle Scholar
  40. George DK, Markelz AG (2012) Terahertz spectroscopy of liquids and biomolecules. In: Terahertz spectroscopy and imaging. Springer, Berlin, pp 229–250. doi: 10.1007/978-3-642-29564-5_9
  41. Grischkowsky DR, Keiding S, Vanexter M, Fattinger C (1990) Far-infrared time-domain spectroscopy with terahertz beams of dielectrics and semiconductors. J Opt Soc Am B 7(10):2006–2015CrossRefGoogle Scholar
  42. Grzybowska K, Paluch M, Grzybowski A, Wojnarowska Z, Hawelek L, Kolodziejczyk K, Ngai KL (2010) Molecular dynamics and physical stability of amorphous anti-inflammatory drug: celecoxib. J Phys Chem B 114(40):12792–12801. doi: 10.1021/jp1040212 PubMedCrossRefGoogle Scholar
  43. Haaser M, Naelapaa K, Gordon KC, Pepper M, Rantanen J, Strachan CJ, Taday PF, Zeitler JA, Rades T (2013) Evaluating the effect of coating equipment on tablet film quality using terahertz pulsed imaging. Eur J Pharm Biopharm 85(3):1095–1102. doi: 10.1016/j.ejpb.2013.03.019 PubMedCrossRefGoogle Scholar
  44. He Y, Ku P, Knab J, Chen J, Markelz A (2008) Protein dynamical transition does not require protein structure. Phys Rev Lett 101(17):178103–178104. doi: 10.1103/PhysRevLett.101.178103 PubMedCrossRefGoogle Scholar
  45. Henry SC, Zurk LM, Schecklman S, Duncan DD (2012) Three-dimensional broadband terahertz synthetic aperture imaging. Opt Eng 51(9):091603-1–091603-9. doi: 10.1117/1.OE.51.9.091603
  46. Heugen U, Schwaab G, Brundermann E, Heyden M, Yu X, Leitner D, Havenith M (2006) Solute-induced retardation of water dynamics probed directly by terahertz spectroscopy. Proc Natl Acad Sci U S A 103(33):12301–12306. doi: 10.1073/pnas.0604897103 PubMedPubMedCentralCrossRefGoogle Scholar
  47. Hisazumi J, Suzuki T, Nakagami H, Terada K (2011) Quantification of pharmaceutical polymorphs and prediction of dissolution rate using theophylline tablet by terahertz spectroscopy. Chem Pharm Bull 59(4):442–446. doi: 10.1248/cpb.59.442 PubMedCrossRefGoogle Scholar
  48. Hisazumi J, Suzuki T, Wakiyama N (2012a) Chemical mapping of hydration and dehydration process of theophylline in tablets using terahertz pulsed imaging. Chem Pharm Bull (Tokyo) 60(7):831–836. doi: 10.1248/cpb.c11-00007 CrossRefGoogle Scholar
  49. Hisazumi J, Watanabe T, Suzuki T (2012b) Using terahertz reflectance spectroscopy to quantify drug substance in tablets. Chem Pharm Bull (Tokyo) 60(12):1487–1493. doi: 10.1248/cpb.c12-00524 CrossRefGoogle Scholar
  50. Ho L, Mueller R, Romer M, Gordon KC, Heinamaki J, Kleinebudde P, Pepper M, Rades T, Shen YC, Strachan CJ, Taday PF, Zeitler JA (2007) Analysis of sustained-release tablet film coats using terahertz pulsed imaging. J Control Release 119(3):253–261. doi: 10.1016/j.jconrel.2007.03.011 PubMedCrossRefGoogle Scholar
  51. Ho L, Mueller R, Gordon KC, Kleinebudde P, Pepper M, Rades T, Shen Y, Taday PF, Zeitler JA (2008) Applications of terahertz pulsed imaging to sustained-release tablet film coating quality assessment and dissolution performance. J Control Release 127(1):79–87. doi: 10.1016/j.jconrel.2008.01.002 PubMedCrossRefGoogle Scholar
  52. Ho L, Mueller R, Gordon KC, Kleinebudde P, Pepper M, Rades T, Shen Y, Taday PF, Zeitler JA (2009a) Monitoring the Film Coating Unit Operation and Predicting Drug Dissolution Using Terahertz Pulsed Imaging. J Pharm Sci 98(12):4866–4876. doi: 10.1002/jps.21766 PubMedCrossRefGoogle Scholar
  53. Ho L, Mueller R, Gordon KC, Kleinebudde P, Pepper M, Rades T, Shen Y, Taday PF, Zeitler JA (2009b) Terahertz pulsed imaging as an analytical tool for sustained-release tablet film coating. Eur J Pharm Biopharm 71(1):117–123. doi: 10.1016/j.ejpb.2008.06.023 PubMedCrossRefGoogle Scholar
  54. Ho L, Mueller R, Krueger C, Gordon KC, Kleinebudde P, Pepper M, Rades T, Shen Y, Taday PF, Zeitler JA (2010) Investigating dissolution performance critical areas on coated tablets: a case study using terahertz pulsed imaging. J Pharm Sci 99(1):392–402. doi: 10.1002/jps.21845 PubMedCrossRefGoogle Scholar
  55. Hongwei L, Zhiyong W (2011) Investigation of solid-state reaction by terahertz time-domain spectroscopy. Nucl Sci Tech 22:139–143Google Scholar
  56. Jepsen PU, Clark S (2007) Precise ab-initio prediction of terahertz vibrational modes in crystalline systems. Chem Phys Lett 442(4-6):275–280CrossRefGoogle Scholar
  57. Jepsen PU, Cooke DG, Koch M (2010) Terahertz spectroscopy and imaging—modern techniques and applications. Laser Photonics Rev 5(1):124–166. doi: 10.1002/lpor.201000011 CrossRefGoogle Scholar
  58. Johari GP (1970) Viscous liquids and the glass transition. II. Secondary relaxations in glasses of rigid molecules. J Chem Phys 53(6):2372–2388. doi: 10.1063/1.1674335 CrossRefGoogle Scholar
  59. Julian Quodbach PK, Kleinebudde P (2015) A critical review on tablet disintegration. Pharm Dev Technol 00(00):1–12. doi: 10.3109/10837450.2015.1045618 CrossRefGoogle Scholar
  60. Juliano TR, King MD, Korter TM (2013) Evaluating London dispersion force corrections in crystalline nitroguanidine by terahertz spectroscopy. IEEE Trans Terahertz Sci Technol 3(3):281–287. doi: 10.1109/TTHZ.2013.2254483 CrossRefGoogle Scholar
  61. Juuti M, Tuononen H, Prykäri T, Kontturi V, Kuosmanen M, Alarousu E, Ketolainen J, Myllylä R, Peiponen KE (2009) Optical and terahertz measurement techniques for flat-faced pharmaceutical tablets: a case study of gloss, surface roughness and bulk properties of starch acetate tablets. Meas Sci Technol 20(1):015,301. doi: 10.1088/0957-0233/20/1/015301 CrossRefGoogle Scholar
  62. Kambara O, Tominaga K, Ji N, Sasaki T, Wang HW, Hayashi M (2010) Mode assignment of vibrational bands of 2-furoic acid in the terahertz frequency region. Chem Phys Lett 498(1–3):86–89. doi: 10.1016/j.cplett.2010.08.047 CrossRefGoogle Scholar
  63. Katz G, Zybin S, Goddard WA III, Zeiri Y, Kosloff R (2014) Direct MD simulations of terahertz absorption and 2D spectroscopy applied to explosive crystals. J Phys Chem Lett 5(5):772–776. doi: 10.1021/jz402801m PubMedCrossRefGoogle Scholar
  64. King M, Korter T (2010) Effect of waters of crystallization on terahertz spectra: anhydrous oxalic acid and its dihydrate. J Phys Chem A 114(26):7127–7138. doi: 10.1021/jp101935n PubMedCrossRefGoogle Scholar
  65. King M, Buchanan W, Korter T (2010a) Investigating the anharmonicity of lattice vibrations in water-containing molecular crystals through the terahertz spectroscopy of L-serine monohydrate. J Phys Chem A 114(35):9570–9578. doi: 10.1021/jp105384x PubMedCrossRefGoogle Scholar
  66. King MD, Buchanan WD, Korter TM (2010b) Understanding the terahertz spectra of crystalline pharmaceuticals: terahertz spectroscopy and solid-state density functional theory study of (S)-(+)-ibuprofen and (RS)-ibuprofen. J Pharm Sci 100(3):1116–1129. doi: 10.1002/jps.22339 PubMedCrossRefGoogle Scholar
  67. King MD, Buchanan WD, Korter TM (2011a) Application of London-type dispersion corrections to the solid-state density functional theory simulation of the terahertz spectra of crystalline pharmaceuticals. Phys Chem Chem Phys 13(10):4250–4259. doi: 10.1039/c0cp01595d PubMedCrossRefGoogle Scholar
  68. King MD, Buchanan WD, Korter TM (2011b) Identification and quantification of polymorphism in the pharmaceutical compound diclofenac acid by terahertz spectroscopy and solid-state density functional theory. Anal Chem 83(10):3786–3792. doi: 10.1021/ac2001934 PubMedCrossRefGoogle Scholar
  69. King MD, Davis EA, Smith TM, Korter TM (2011c) Importance of accurate spectral simulations for the analysis of terahertz spectra: citric acid anhydrate and monohydrate. J Phys Chem A 115(40):11039–11044PubMedCrossRefGoogle Scholar
  70. Knab J, Chen J, Markelz A (2006) Hydration dependence of conformational dielectric relaxation of lysozyme. Biophys J 90(7):2576–2581. doi: 10.1529/biophysj.105.069088 PubMedPubMedCentralCrossRefGoogle Scholar
  71. Kogermann K, Zeitler JA, Rantanen J, Rades T, Taday PF, Pepper M, Heinämäki J, Strachan CJ (2007) Investigating dehydration from compacts using terahertz pulsed, Raman, and near-infrared spectroscopy. Appl Spectrosc 61(12):1265–1274. doi: 10.1366/000370207783292136 PubMedCrossRefGoogle Scholar
  72. Lee YS (2009) Principles of THz science and technology. Springer, BostonGoogle Scholar
  73. Li R, Zeitler JA, Tomerini D, Parrott EPJ, Gladden LF, Day G (2010) A study into the effect of subtle structural details and disorder on the terahertz spectrum of crystalline benzoic acid. Phys Chem Chem Phys 12(20):5329–5340. doi: 10.1039/b926536h PubMedCrossRefGoogle Scholar
  74. Li C, Zeitler JA, Dong Y, Shen YC (2014) Non-destructive evaluation of polymer coating structures on pharmaceutical pellets using full-field optical coherence tomography. J Pharm Sci 103(1):161–166. doi: 10.1002/jps.23764 CrossRefPubMedGoogle Scholar
  75. Lin H, May RK, Evans MJ, Zhong S, Gladden LF, Shen Y, Zeitler JA (2015) Impact of processing conditions on inter-tablet coating thickness variations measured by terahertz in-line sensing. J Pharm Sci 104(8):2513–2522. doi: 10.1002/jps.24503 PubMedPubMedCentralCrossRefGoogle Scholar
  76. Liu H, Zhang X (2006) Dehydration kinetics of D-glucose monohydrate studied using THz time-domain spectroscopy. Chem Phys Lett 429(1–3):229–233CrossRefGoogle Scholar
  77. Liu X, Liu G, Zhao H, Zhang Z, Wei Y, Liu M, Wen W, Zhou X (2011) The quantitative monitoring of mechanochemical reaction between solid l-tartaric acid and sodium carbonate monohydrate by terahertz spectroscopy. J Phys Chem Solids 72(11):1245–1250. doi: 10.1016/j.jpcs.2011.07.011 CrossRefGoogle Scholar
  78. Lowenthal W (1972) Disintegration of tablets. J Pharm Sci 61(11):1695–1711. doi: 10.1002/jps.2600611102 PubMedCrossRefGoogle Scholar
  79. Lu M, Shen J, Li N, Zhang Y, Zhang C, Liang L, Xu X (2006) Detection and identification of illicit drugs using terahertz imaging. J Appl Phys 100(10):103104. doi: 10.1063/1.2388041 CrossRefGoogle Scholar
  80. Malaterre V, Pedersen M, Ogorka J, Gurny R, Loggia N, Taday PF (2009) Terahertz pulsed imaging, a novel process analytical tool to investigate the coating characteristics of push-pull osmotic systems. Eur J Pharm Biopharm 74(1):21–25CrossRefGoogle Scholar
  81. Markelz A, Knab J, Chen J, He Y (2007) Protein dynamical transition in terahertz dielectric response. Chem Phys Lett 442(4–6):413–417CrossRefGoogle Scholar
  82. Maurer L, Leuenberger H (2009) Terahertz pulsed imaging and near infrared imaging to monitor the coating process of pharmaceutical tablets. Int J Pharm 370(1–2):8–16. doi: 10.1016/j.ijpharm.2008.11.011 PubMedCrossRefGoogle Scholar
  83. May R, Evans MJ, Zhong S, Warr I, Gladden LF, Shen Y, Zeitler JA (2011) Terahertz in-line sensor for direct coating thickness measurement of individual tablets during film coating in real-time. J Pharm Sci 100(4):1535–1544. doi: 10.1002/jps.22359 PubMedCrossRefGoogle Scholar
  84. May R, Su K, Han L, Zhong S, Elliott JA, Gladden LF, Evans M, Shen Y, Zeitler JA (2013) Hardness and density distributions of pharmaceutical tablets measured by terahertz pulsed imaging. J Pharm Sci 102:2179–2186. doi: 10.1002/jps.23560 PubMedCrossRefGoogle Scholar
  85. McIntosh AI, Yang B, Goldup SM, Watkinson M, Donnan RS (2013) Crystallization of amorphous lactose at high humidity studied by terahertz time domain spectroscopy. Chem Phys Lett 558:104–108. doi: 10.1016/j.cplett.2012.12.044 CrossRefGoogle Scholar
  86. Möller KD, Rothschild WG (1971) Far-infrared spectroscopy. Wiley-VCH Verlag, WeinheimGoogle Scholar
  87. Müller J, Brock D, Knop K, Zeitler JA, Kleinebudde P (2012) Prediction of dissolution time and coating thickness of sustained release formulations using Raman spectroscopy and terahertz pulsed imaging. Eur J Pharm Biopharm 80(3):690–697. doi: 10.1016/j.ejpb.2011.12.003 PubMedCrossRefGoogle Scholar
  88. Ngai KL (1998) Relation between some secondary relaxations and the α relaxations in glass-forming materials according to the coupling model. J Chem Phys 109(16):6982. doi: 10.1063/1.477334 CrossRefGoogle Scholar
  89. Ngai KL (2003) An extended coupling model description of the evolution of dynamics with time in supercooled liquids and ionic conductors. J Phys Condens Matter 15(11):S1107–S1125CrossRefGoogle Scholar
  90. Nguyen K, Friscic T, Day G, Gladden LF, Jones W (2007) Terahertz time-domain spectroscopy and the quantitative monitoring of mechanochemical cocrystal formation. Nat Mater 6(3):206–209. doi: 10.1038/nmat1848 PubMedCrossRefGoogle Scholar
  91. Ning L, Jingling S, Jinhai S, Laishun L, Xiaoyu X, Meihong L, Yan J (2005) Study on the THz spectrum of methamphetamine. Opt Express 13(18):6750–6755PubMedCrossRefGoogle Scholar
  92. Niwa M, Hiraishi Y (2014) Quantitative analysis of visible surface defect risk in tablets during film coating using terahertz pulsed imaging. Int J Pharm 461(1-2):342–350. doi: 10.1016/j.ijpharm.2013.11.051 PubMedCrossRefGoogle Scholar
  93. Niwa M, Hiraishi Y, Iwasaki N, Terada K (2013) Quantitative analysis of the layer separation risk in bilayer tablets using terahertz pulsed imaging. Int J Pharm 452(1–2):249–256. doi: 10.1016/j.ijpharm.2013.05.010 PubMedCrossRefGoogle Scholar
  94. Niwa M, Hiraishi Y, Terada K (2014) Evaluation of coating properties of enteric-coated tablets using terahertz pulsed imaging. Pharm Res 31(8):2140–2151. doi: 10.1007/s11095-014-1314-6 PubMedCrossRefGoogle Scholar
  95. Otsuka M, Nishizawa J, Shibata J, Ito M (2010) Quantitative evaluation of mefenamic acid polymorphs by terahertz-chemometrics. J Pharm Sci 99(9):4048–4053PubMedCrossRefGoogle Scholar
  96. Palermo R, Cogdill R, Short S, Drennen Iii J, Taday PF (2008) Density mapping and chemical component calibration development of four-component compacts via terahertz pulsed imaging. J Pharm Biomed Anal 46(1):36–44. doi: 10.1016/j.jpba.2007.10.023 PubMedCrossRefGoogle Scholar
  97. Parrott EPJ, Zeitler JA, Friscic T, Pepper M, Jones W, Day G, Gladden LF (2009) Testing the sensitivity of terahertz spectroscopy to changes in molecular and supramolecular structure: a study of structurally similar cocrystals. Cryst Growth Des 9(3):1452–1460. doi: 10.1021/cg8008893 CrossRefGoogle Scholar
  98. Parrott EPJ, Zeitler JA, Simon G, Hehlen B, Gladden LF, Taraskin SN, Elliott SR (2010) Atomic charge distribution in sodosilicate glasses from terahertz time-domain spectroscopy. Phys Rev B Condens Matter 82(14):140203(R). doi: 10.1103/PhysRevB.82.140203
  99. Parrott EPJ, Zeitler JA (2015) Terahertz time-domain and low-frequency Raman spectroscopy of organic materials. Appl Spectrosc 69(1):1–25Google Scholar
  100. Peiponen KE, Zeitler JA, Kuwata-Gonokami M (eds) (2013) Terahertz spectroscopy and imaging, Springer series in optical sciences, vol 171. Springer, Berlin. doi: 10.1007/978-3-642-29564-5
  101. Peiponen KE, Bawuah P, Chakraborty M, Juuti M, Zeitler JA, Ketolainen J (2015) Estimation of Young’s modulus of pharmaceutical tablet obtained by terahertz time-delay measurement. Int J Pharm 489(1–2):100–105. doi: 10.1016/j.ijpharm.2015.04.068 PubMedCrossRefGoogle Scholar
  102. Pellizzeri S, Delaney SP, Korter TM, Zubieta J (2014) Using terahertz spectroscopy and solid-state density functional theory to characterize a new polymorph of 5-(4-pyridyl)tetrazole. J Phys Chem A 118(2):417–426. doi: 10.1021/jp412142w PubMedCrossRefGoogle Scholar
  103. Ronne C, Jensby K, Madsen GKH, Nielsen OF, Keiding SR (1999) THz time domain spectroscopy of liquids. In: Chamberlain JM (ed) Industrial lasers and inspection (EUROPTO series), SPIE, pp 266–275. doi: 10.1117/12.361045
  104. Rungsawang R, Ueno Y, Tomita I, Ajito K (2006a) Angle-dependent terahertz time-domain spectroscopy of amino acid single crystals. J Phys Chem B 110(42):21259–21263PubMedCrossRefGoogle Scholar
  105. Rungsawang R, Ueno Y, Tomita I, Ajito K (2006b) Terahertz notch filter using intermolecular hydrogen bonds in a sucrose crystal. Opt Express 14(12):5765–5772PubMedCrossRefGoogle Scholar
  106. Russe IS, Brock D, Knop K, Kleinebudde P, Zeitler JA (2012) Validation of terahertz coating thickness measurements using X-ray microtomography. Mol Pharm 9(12):3551–3559. doi: 10.1021/mp300383y PubMedCrossRefGoogle Scholar
  107. Sakamoto T, Portieri A, Taday PF (2009) Detection of tulobuterol crystal in transdermal patches using terahertz pulsed spectroscopy and imaging. Pharmazie 64(6):361–365. doi: 10.1691/ph.2009.9022 PubMedGoogle Scholar
  108. Sakamoto T, Portieri A, Arnone DD, Taday PF, Kawanishi T, Hiyama Y (2012) Coating and density distribution analysis of commercial ciprofloxacin hydrochloride monohydrate tablets by terahertz pulsed spectroscopy and imaging. J Pharm Innov 7(2):87–93. doi: 10.1007/s12247-012-9130-1 PubMedPubMedCentralCrossRefGoogle Scholar
  109. Shen Y, Taday PF (2008) Development and application of terahertz pulsed imaging for nondestructive inspection of pharmaceutical tablet. IEEE J Sel Top Quantum Electron 14(2):407–415. doi: 10.1109/.2007.JSTQE.911309 CrossRefGoogle Scholar
  110. Shen Y, Upadhya P, Linfield E, Davies A (2003) Temperature-dependent low-frequency vibrational spectra of purine and adenine. Appl Phys Lett 82(14):2350–2352CrossRefGoogle Scholar
  111. Shen Y, Upadhya P, Linfield E, Davies A (2004) Vibrational spectra of nucleosides studied using terahertz time-domain spectroscopy. Vib Spectrosc 35(1–2):111–114CrossRefGoogle Scholar
  112. Shen Y, Taday PF, Newnham D, Kemp M, Pepper M, Hwu R, Linden K (2005a) 3D chemical mapping using terahertz pulsed imaging. In: Terahertz and gigahertz electronics and photonics IV, pp 24–31. doi: 10.1117/12.591472
  113. Shen Y, Taday PF, Newnham D, Pepper M (2005a) Chemical mapping using reflection terahertz pulsed imaging. Semicond Sci Technol 20(7):S254–S257CrossRefGoogle Scholar
  114. Sibik J, Zeitler JA (2015) Study of disordered materials by terahertz spectroscopy. Wiley, New York, p 26Google Scholar
  115. Sibik J, Shalaev EY, Zeitler JA (2013) Glassy dynamics of sorbitol solutions at terahertz frequencies. Phys Chem Chem Phys 15(28):11931–11942. doi: 10.1039/c3cp51936h PubMedCrossRefGoogle Scholar
  116. Sibik J, Elliott SR, Zeitler JA (2014a) Thermal decoupling of molecular-relaxation processes from the vibrational density of states at terahertz frequencies in supercooled hydrogen-bonded liquids. J Phys Chem Lett 5(11):1968–1972. doi: 10.1021/jz5007302 PubMedCrossRefGoogle Scholar
  117. Sibik J, Sargent MJ, Franklin M, Zeitler JA (2014b) Crystallization and phase changes in paracetamol from the amorphous solid to the liquid phase. Mol Pharm 11(4):1326–1334. doi: 10.1021/mp400768m PubMedPubMedCentralCrossRefGoogle Scholar
  118. Sibik J, Löbmann K, Rades T, Zeitler JA (2015) Predicting crystallization of amorphous drugs with terahertz spectroscopy. Mol Pharm 12(8):3062–3068. doi: 10.1021/acs.molpharmaceut.5b00330 PubMedCrossRefGoogle Scholar
  119. Singh R, George DK, Benedict JB, Korter TM, Markelz AG (2012) Improved mode assignment for molecular crystals through anisotropic terahertz spectroscopy. J Phys Chem 116(42):10359–10364. doi: 10.1021/jp307288r CrossRefGoogle Scholar
  120. Smith G, Hussain A, Bukhari NI, Ermolina I (2015a) Quantification of residual crystallinity in ball milled commercially sourced lactose monohydrate by thermo-analytical techniques and terahertz spectroscopy. Eur J Pharm Biopharm 92:180–191. doi: 10.1016/j.ejpb.2015.02.026 PubMedCrossRefGoogle Scholar
  121. Smith G, Hussain A, Bukhari NI, Ermolina I (2015b) Quantification of residual crystallinity of ball-milled, commercially available, anhydrous β-lactose by differential scanning calorimetry and terahertz spectroscopy. J Therm Anal Calorim 121(1):327–333. doi: 10.1007/s10973-015-4469-4 CrossRefGoogle Scholar
  122. Spencer J, Gao Z, Moore T, Buhse L, Taday PF, Newnham D, Shen Y, Portieri A, Husain A (2008) Delayed release tablet dissolution related to coating thickness by terahertz pulsed image mapping. J Pharm Sci 97(4):1543–1550. doi: 10.1002/jps.21051 PubMedCrossRefGoogle Scholar
  123. Strachan CJ, Rades T, Newnham D, Gordon KC, Pepper M, Taday PF (2004) Using terahertz pulsed spectroscopy to study crystallinity of pharmaceutical materials. Chem Phys Lett 390(1–3):20–24. doi: 10.1016/j.cplett.2004.03.117 CrossRefGoogle Scholar
  124. Strachan CJ, Taday PF, Newnham DA, Gordon KC, Zeitler JA, Pepper M, Rades T (2005) Using terahertz pulsed spectroscopy to quantify pharmaceutical polymorphism and crystallinity. J Pharm Sci 94(4):837–846. doi: 10.1002/jps.20281 PubMedCrossRefGoogle Scholar
  125. Su K, Shen YC, Zeitler JA (2014) Terahertz sensor for non-contact thickness and quality measurement of automobile paints of varying complexity. IEEE Trans Terahertz Sci Technol 4(4):432–439. doi: 10.1109/TTHZ.2014.2325393 CrossRefGoogle Scholar
  126. Taday PF, Bradley IV, Arnone DD (2003a) Terahertz pulse spectroscopy of biological materials: L-glutamic acid. J Biol Phys 29(2-3):109–115. doi: 10.1023/A:1024424205309 PubMedPubMedCentralCrossRefGoogle Scholar
  127. Taday PF, Bradley IV, Arnone DD, Pepper M (2003b) 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(4):831–838. doi: 10.1002/jps.10358 PubMedCrossRefGoogle Scholar
  128. Takahashi M (2014) Terahertz vibrations and hydrogen-bonded networks in crystals. Crystals 4(2):74–103. doi: 10.3390/cryst4020074 CrossRefGoogle Scholar
  129. Takahashi M, Kawazoe Y, Ishikawa Y, Ito H (2009) Interpretation of temperature-dependent low frequency vibrational spectrum of solid-state benzoic acid dimer. Chem Phys Lett 479(4–6):211–217. doi: 10.1016/j.cplett.2009.08.017 CrossRefGoogle Scholar
  130. Takeuchi I, Tomoda K, Nakajima T, Terada H, Kuroda H, Makino K (2012) Estimation of crystallinity of trehalose dihydrate microspheres by usage of terahertz time-domain spectroscopy. J Pharm Sci 101(9):3465–3472. doi: 10.1002/jps.23147 PubMedCrossRefGoogle Scholar
  131. Takeuchi I, Shimakura K, Ohtake H, Takayanagi J, Tomoda K, Nakajima T, Terada H, Makino K (2014) Nondestructive analysis of structure and components of tablet coated with film by the usage of terahertz time-domain reflection spectroscopy. J Pharm Sci 103(1):256–261. doi: 10.1002/jps.23797 PubMedCrossRefGoogle Scholar
  132. Tan NY, Zeitler JA (2015) Probing phase transitions in simvastatin with terahertz time-domain spectroscopy. Mol Pharm 12(3):810–815. doi: 10.1021/mp500649q PubMedCrossRefGoogle Scholar
  133. Taraskin SN, Simdyankin S, Elliott SR, Neilson J, Lo T (2006) Universal features of terahertz absorption in disordered materials. Phys Rev Lett 97:055504PubMedCrossRefGoogle Scholar
  134. Threlfall T (2014) Polymorphism—polymorph myths and misperceptions. Eur Pharm Rev 19(3):24–29Google Scholar
  135. Tomerini D, Day GM (2012) Computational methods for the assignment of vibrational modes in crystalline materials. In: Terahertz spectroscopy and imaging. Springer, Berlin, pp 151–190. doi: 10.1007/978-3-642-29564-5_7
  136. Tuononen H, Fukunaga K, Kuosmanen M, Ketolainen J, Peiponen KE (2010a) Wiener bounds for complex permittivity in terahertz spectroscopy: case study of two-phase pharmaceutical tablets. Appl Spectrosc 64(1):127–131PubMedCrossRefGoogle Scholar
  137. Tuononen H, Gornov E, Zeitler JA, Aaltonen J, Peiponen KE (2010b) Using modified Kramers-Kronig relations to test transmission spectra of porous media in THz-TDS. Opt Lett 35(5):631–633PubMedCrossRefGoogle Scholar
  138. Ueno Y, Ajito K (2007) Terahertz time-domain spectra of aromatic carboxylic acids incorporated in nano-sized pores of mesoporous silicate. Anal Sci 23(7):803–807PubMedCrossRefGoogle Scholar
  139. Ueno Y, Rungsawang R, Tomita I, Ajito K (2006a) Quantitative measurements of amino acids by terahertz time-domain transmission spectroscopy. Anal Chem 78(15):5424–5428PubMedCrossRefGoogle Scholar
  140. Ueno Y, Rungsawang R, Tomita I, Ajito K (2006b) Terahertz time-domain spectra of inter- and intramolecular hydrogen bonds of fumaric and maleic acids. Chem Lett 35(10):1128–1129CrossRefGoogle Scholar
  141. Upadhya P, Shen Y, Davies A, Linfield E (2003) Terahertz time-domain spectroscopy of glucose and uric acid. J Biol Phys 29(2–3):117–121. doi: 10.1023/A:1024476322147 PubMedPubMedCentralCrossRefGoogle Scholar
  142. Upadhya P, Shen Y, Davies A, Linfield E (2004) Far-infrared vibrational modes of polycrystalline saccharides. Vib Spectrosc 35(1–2):139–143CrossRefGoogle Scholar
  143. Upadhya P, Nguyen K, Shen Y, Obradovic J, Fukushige K, Griffiths R, Gladden LF, Davies A, Linfield E (2006) Characterization of crystalline phase-transformations in theophylline by time-domain terahertz spectroscopy. Spectrosc Lett 39(3):215–224CrossRefGoogle Scholar
  144. Vanexter M, Fattinger C, Grischkowsky DR (1989) Terahertz time-domain spectroscopy of water-vapor. Opt Lett 14(20):1128–1130CrossRefGoogle Scholar
  145. Vieira FS, Pasquini C (2014) Determination of cellulose crystallinity by terahertz-time domain spectroscopy. Anal Chem 86(8):3780–3786. doi: 10.1021/ac4035746 PubMedCrossRefGoogle Scholar
  146. Vynckier AK, Lin H, Zeitler JA, Willart JF, Bongaers E, Voorspoels J, Remon JP, Vervaet C (2015) Calendering as a direct shaping tool for the continuous production of fixed-dose combination products via co-extrusion. Eur J Pharm Biopharm 96:125–131. doi: 10.1016/j.ejpb.2015.07.023 PubMedCrossRefGoogle Scholar
  147. Walther M, Fischer B, Schall M, Helm H, Jepsen PU (2000) Far-infrared vibrational spectra of all-trans, 9-cis and 13-cis retinal measured by THz time-domain spectroscopy. Chem Phys Lett 332(3–4):389–395CrossRefGoogle Scholar
  148. Walther M, Plochocka P, Fischer B, Helm H, Jepsen PU (2002) Collective vibrational modes in biological molecules investigated by terahertz time-domain spectroscopy. Biopolymers 67(4–5):310–313PubMedCrossRefGoogle Scholar
  149. Walther M, Fischer B, Jepsen PU (2003) Noncovalent intermolecular forces in polycrystalline and amorphous saccharides in the far infrared. Chem Phys 288(2–3):261–268CrossRefGoogle Scholar
  150. Wu H, Heilweil EJ, Hussain A, Khan M (2008) Process analytical technology (PAT): quantification approaches in Terahertz spectroscopy for pharmaceutical application. J Pharm Sci 97(2):970–984PubMedCrossRefGoogle Scholar
  151. Yada H, Nagai M, Tanaka K (2009) The intermolecular stretching vibration mode in water isotopes investigated with broadband terahertz time-domain spectroscopy. Chem Phys Lett 473(4–6):279–283. doi: 10.1016/j.cplett.2009.03.075 CrossRefGoogle Scholar
  152. Yamaguchi M, Miyamaru F, Yamamoto K, Tani M, Hangyo M (2005) Terahertz absorption spectra of L-, D-, and DL-alanine and their application to determination of enantiometric composition. Appl Phys Lett 86(5):053903-1–053903-3Google Scholar
  153. Yassin S, Goodwin DJ, Anderson A, Sibik J, Wilson DI, Gladden LF, Zeitler JA (2015a) The disintegration process in microcrystalline cellulose based tablets, Part 1: influence of temperature, porosity and superdisintegrants. J Pharm Sci 104(10):3440–3450. doi: 10.1002/jps.24544 PubMedPubMedCentralCrossRefGoogle Scholar
  154. Yassin S, Su K, Lin H, Gladden LF, Zeitler JA (2015b) Diffusion and swelling measurements in pharmaceutical powder compacts using terahertz pulsed imaging. J Pharm Sci 104(5):1658–1667. doi: 10.1002/jps.24376 PubMedPubMedCentralCrossRefGoogle Scholar
  155. Zalkovskij M, Zoffmann Bisgaard C, Novitsky A, Malureanu R, Savastru D, Popescu A, Jepsen PU, Lavrinenko AV (2012) Ultrabroadband terahertz spectroscopy of chalcogenide glasses. Appl Phys Lett 100(3):031901. doi: 10.1063/1.3676443 CrossRefGoogle Scholar
  156. Zeitler JA, Gladden LF (2009) In-vitro tomography and non-destructive imaging at depth of pharmaceutical solid dosage forms. Eur J Pharm Biopharm 71(1):2–22. doi: 10.1016/j.ejpb.2008.08.012 PubMedCrossRefGoogle Scholar
  157. Zeitler JA, Shen YC (2012) Industrial applications of terahertz imaging. In: Terahertz spectroscopy and imaging. Springer, Berlin, pp 451–489. doi: 10.1007/978-3-642-29564-5_18
  158. Zeitler JA, Newnham DA, Taday PF, Strachan CJ, Pepper M, Gordon KC, Rades T (2005) Temperature dependent terahertz pulsed spectroscopy of carbamazepine. Thermochim Acta 436(1–2):71–77. doi: 10.1016/j.tca.2005.07.006 CrossRefGoogle Scholar
  159. Zeitler JA, Newnham DA, Taday PF, Threlfall TL, Lancaster RW, Berg RW, Strachan CJ, Pepper M, Gordon KC, Rades T (2006) Characterization of temperature-induced phase transitions in five polymorphic forms of sulfathiazole by terahertz pulsed spectroscopy and differential scanning calorimetry. J Pharm Sci 95(11):2486–2498. doi: 10.1002/jps.20719 PubMedCrossRefGoogle Scholar
  160. Zeitler JA, Taday PF, Gordon KC, Pepper M, Rades T (2007a) Solid-state transition mechanism in carbamazepine polymorphs by time-resolved terahertz spectroscopy. ChemPhysChem 8(13):1924–1927. doi: 10.1002/cphc.200700261 PubMedCrossRefGoogle Scholar
  161. Zeitler JA, Taday PF, Pepper M, Rades T (2007b) Relaxation and crystallization of amorphous carbamazepine studied by terahertz pulsed spectroscopy. J Pharm Sci 96(10):2703–2709. doi: 10.1002/jps.20908 PubMedCrossRefGoogle Scholar
  162. Zeitler JA, Kogermann K, Rantanen J, Rades T, Taday PF, Pepper M, Aaltonen J, Strachan CJ (2007c) Drug hydrate systems and dehydration processes studied by terahertz pulsed spectroscopy. Int J Pharm 334(1–2):78–84. doi: 10.1016/j.ijpharm.2006.10.027 PubMedCrossRefGoogle Scholar
  163. Zeitler JA, Shen Y, Baker C, Taday PF, Pepper M, Rades T (2007d) Analysis of coating structures and interfaces in solid oral dosage forms by three dimensional terahertz pulsed imaging. J Pharm Sci 96(2):330–340. doi: 10.1002/jps.20789 PubMedCrossRefGoogle Scholar
  164. Zhang Q, Gladden LF, Avalle P, Zeitler JA, Mantle M (2013) Terahertz pulsed imaging and magnetic resonance imaging as tools to probe formulation stability. Pharmaceutics 5(4):591–608. doi: 10.3390/pharmaceutics5040591 PubMedPubMedCentralCrossRefGoogle Scholar
  165. Zhong S, Shen Y, Shen H, Evans M, May R, Zeitler JA, Warr I (2010) Near-infrared spectroscopy for non-destructive coating analysis calibrated by terahertz pulsed imaging. In: 35th international conference on infrared millimeter and terahertz waves (IRMMW-THz), pp 1–2. doi: 10.1109/ICIMW.2010.5612668
  166. Zhong S, Shen YC, Ho L, May R, Zeitler JA, Evans M, Taday PF, Pepper M, Rades T, Gordon KC, Mueller R, Kleinebudde P (2011) Non-destructive quantification of pharmaceutical tablet coatings using terahertz pulsed imaging and optical coherence tomography. Opt Lasers Eng 49(3):361–365. doi: 10.1016/j.optlaseng.2010.11.003 CrossRefGoogle Scholar

Copyright information

© Controlled Release Society 2016

Authors and Affiliations

  1. 1.Department of Chemical Engineering and BiotechnologyUniversity of CambridgeCambridgeUK

Personalised recommendations