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1 Netsu Sokutei Application of Thermal Analysis to the Pharmaceutical Development Katsuhide Terada (Received Nov. 25, 2010; Accepted Dec. 21, 2010) The pharmaceutical development challenges various processes from the exploration of potential candidates of API (active pharmaceutical ingredient) to the manufacturing of pharmaceutical products. To ensure the developability of drug candidates, the full understanding of physicochemical characteristics of API is indispensable for the formulation and manufacturing of pharmaceutical product. We have introduced the usefulness of thermal analysis for the evaluation of various physicochemical characteristics of pharmaceuticals from API to pharmaceutical products. In the field of API, such as thermodynamic relative stability of polymorphs, quantitative relationship between dissolution rate and morphology, and crystallization mechanism of amorphous to polymorphs were studied. In the field of pharmaceutical products, such as compatibility of formulation, evaluation of stability of pharmaceuticals, monitoring of wetting and disintegration process, physical stability estimation of solid dispersion, optimum manufacturing process for freeze drying product were studied. Keywords: polymorphs, hydrates, crystallinity, stability, solid dispersion, compatibility, lyophilization, dissolution, disintegration, phase transition The Japan Society of Calorimetry and Thermal Analysis. 46
2 9 1 DSC X 1-10) X DSC ) DSC 13) 1996 ln(dc/dt) Fig.1 ln(dc/dt) Fig.2 heat of solution / kj mol 1 Relationship between heat of solution and logarithms of initial dissolution rate of terfenadine. heat of fusion at 25 / kj mol 1 Relationship between heat of fusion and logarithms of initial dissolution rate of terfenadine. 14) 15) ln (dc/dt) {(1-T/β)/RT} ΔH s + ln k (1) C, ΔH s, β, k Fig.1 DSC DSC 25 ΔH 25 m 16) Fig.2 17) α β X 18) 47
3 heat of solution / kj mol 1 Intensity / cps T / T / K 2θ / Heat Flow / mw Fig.3 Heat of solution of Tolbutamide polymorphs. Fig.4 Simultaneous measurement of XRD-DSC for Tolbutamide form I. 19) 4 II III IV I I I I III Fig.3 40 II I III 40 II III I 40I X -DSC Fig.4 40I 20) I L I H I L 0.37 kj mol 1 K 1 I H 0.33 kj mol 1 K 1 SPring-8 X Fig.5 Fig.5 Comparison of molecular packing between at high temperature phase and at low temperature phase of Tolbutamide. NMR 2-Ethoxy-6,9- diamino-acridine X -DSC Fig A B B A DSC 48
4 Intensity / cps Fig.6 2θ / Heat Flow / mw T / Phase transition of Acrinol Monohydrate by XRD- DSC I I II 22) 21) X -DSC X -DSC I II I 23) RH 95.4 RH ) deconvolution Output / mv Fractional hydration / a t / h t / h Fig.7 Hydration of Theophylline anhydrate powder stored at higher RHs at 25. Thermograms (left) and hydration profiles (right) showing random nucleation and two-dimentional growth of nuclei. 49
5 Fig ) 25 2 /RH /RH75 5 HPLC HPLC ΔH5days / mj g 1 Fig.8 Decomposed amounts of the drug / % Compatibility between heat of decomposition ( H 5days) and amounts of decomposed Oxybutynin HCl assayed by HPLC. 26) Flavoxate Hydrochloride 40 RH53% 40 RH75% 40 RH96% HPLC 95 Fig.8 Oxbutynin Hydrochloride mj g 1 HSD ) RH 3 HPLC HPLC SEFA LASA HPLC X -DSC 29-30) DSC 50
6 ti / min ti 1 / min 1 T / K T / K Fig.9 Effect of temperature on the induction period of crystallization of naproxen containing 50% of HPMCAS. Fig.10 Plot of the homogeneous nucleation rate and the fitting to equation. 31) HPMCAS-LG HG MG 3 DSC t i t i Fig.9 HPMC-AS-LG HG MG HPMC-AS-LG MG HG t i 333 K t i HPMC-AS-LG t i t i I 16πσ 3 T m2 V 2 m ΔF 1/t i A' exp exp (2) 3(T m T) 2 ΔH f2 kt kt σ T m V m ΔH f k Boltzmann T ΔF A' HPMC-AS-LG HG MG 3 t i Fig.10 3 ti curves provided by extrapolation method / year T / K Fig.11 Prediction of induction period of crystallization of naproxen in 50 % HPMCAS at desired temperature. Fig K 3 MG 293 K HG 296 K LG 299 K LG>HG>MG X -DSC DSC 51
7 32-40) 3 DSC T g' T c) T g' T g' T g' T g' 2 T g' 1) Y. Nakai, S. Nakajima, K. Yamamoto, K. Terada, and T. Konno, Chem. Pharm. Bull. 26, 2419 (1978). 2) Y. Nakai, S. Nakajima, K. Yamamoto, K. Terada, and T. Konno, Chem. Pharm. Bull. 28, 652 (1980). 3) Y. Nakai, S. Nakajima, K. Yamamoto, K. Terada, and T. Konno, Chem. Pharm. Bull. 28, 1552 (1980). 4) Y. Nakai, K. Yamamoto, K. Terada, and H. Horibe, Chem. Pharm. Bull. 30, 1796 (1982). 5) Y. Nakai, K. Yamamoto, K. Terada, and H. Horibe, Chem. Pharm. Bull. 31, 3745 (1983). 6) Y. Nakai, K. Yamamoto, K. Terada, and K. Akimoto, Chem. Pharm. Bull. 32, 685 (1984). 7) K. Terada, K. Yamamoto, and Y. Nakai, Labo- Pharma Probl. Tech. 339, 95 (1984). 8) Y. Nakai, K. Yamamoto, K. Terada, and H. Horibe, J. Incl. Phenom. 2, 523 (1984). 9) Y. Nakai, K. Yamamoto, K. Terada, and A. Kajiyama, Chem. Pharm. Bull. 33, 5110 (1985). 10) Y. Nakai, K. Yamamoto, K. Terada, and Y. Ueno, Chem. Pharm. Bull. 34, 315 (1986). 11) Y. Nakai, K. Yamamoto, K. Terada, and J. Ichikawa, Chem. Pharm. Bull. 32, 4566 (1984). 12) Y. Nakai, K. Yamamoto, K. Terada, T. Oguchi and S. Izumikawa, Chem. Pharm. Bull. 34, 4760 (1986). 13) Y. Nakai, K. Yamamoto, K. Terada, and T. Oguchi, Chem. Pharm. Bull. 34, 3549 (1986). 14) K. Terada and Y. Yoshihashi, Netsu Sokutei 25, 105 (1998). 15) E. Yonemochi, Y. Yoshihashi, and K. Terada, Pharm. Res. 17, 90 (2000). 16) K. Terada, H. Kitano, Y. Yoshihashi, and E. Yonemochi, Pharm. Res. 17, 918 (2000). 17) Y. Yoshihashi, H. Kitano, E. Yonemochi, and K. Terada, Int. J. Pharmaceutics. 204, 1 (2000). 18) Y. Yasuo, E. Yonemochi, and K. Terada, Pharm. Dev. Tech. 7, 1 (2002). 19) Y. Yokoi, E. Yonemochi, and K. Terada, Int. J. Pharmaceutics 280, 67 (2004). 20) G. Hasegawa, T. Komasaka, R. Bando, Y. Yoshihashi, E. Yonemochi, K. Fujii, H. Uekusa, and K. Terada, Int. J. Pharm. 369, 12 (2009). 21) K. Fujii, H. Uekusa, N. Itoda, G. Hasegawa, E. Yonemochi, K. Terada, Z. Pan, and K. D. M. Harris, 52
8 J. Phys. Chem. C 114, 580 (2010). 22) E. Yonemochi, T. Hoshino, Y. Yasuo, and K. Terada, Thermochimica Acta 432, 70 (2005). 23) Y. Yoshihashi, M. Makita, S. Yamamura, E. Fukuoka and K. Terada, Chem. Pharm. Bull. 46, 473 (1998). 24) Y. Yoshihashi, M. Makita, S. Yamamura, E. Fukuoka and K. Terada, Chem. Pharm. Bull. 46, 1148 (1998). 25) Y. Yoshihashi, E. Yonemochi, M. Makita, S. Yamamura, E. Fukuoka, and K. Terada, Chem. Pharm. Bull. 48, 208 (2000). 26) Y. Yoshihashi, E. Yonemochi and K. Terada, Netsu Sokutei 31, 80 (2004). 27) Y. Yoshihashi, T. Masuda, S. Matsumaru, Y. Morimoto, E. Yonemochi, and K. Terada, Yakuzaigaku 64, 370 (2004). 28) K. Terada, T. Masuda, Y. Yoshihashi, and E. Yonemochi, Journal of Thermal Analysis and Calorimetry 85, 675 (2006). 29) Y. Yoshihashi, H. Iijima, E. Yonemochi, and K. Terada, Journal of Thermal Analysis and Calorimetry 85, (2006). 30) S. Hasegawa, T. Hamaura, N. Furuyama, S. Horikawa, A. Kusai, E. Yonemochi, and K. Terada, Int. J. Pharmaceutics 280, (2004). 31) Y. Yoshihashi, E. Yonemochi, Y. Maeda, and K. Terada, J. Thermal Analysis and Calorimetry 99, 15 (2010). 32) H. Egawa, E. Yonemochi, and K. Terada, Thermochimica Acta 431, (2005). 33) E. Yonemochi, Y. Yoshioka, Y. Yoshihashi, and K. Terada, Journal of Thermal Analysis and Calorimetry 85, (2006). 34) T. Ito, Y. Yoshioka, Y. Yoshihashi, E. Yonemochi, and K. Terada, Journal of Thermal Analysis and Calorimetry 85, (2006). 35) K. Izutsu, S. Kadoya, C. Yomota, T. Kawanishi, Y. Yoshihashi, E. Yonemochi, and K. Terada, Cryobiological and Cryotechnology 53, (2007). 36) S. Kadoya, K. Izutsu, E. Yonemochi, K. Terada, C. Yomota, and T. Kawanishi, Chem. Pharm. Bull. 56, (2008). 37) K. Izutsu, C. Yomota, T. Kawanishi, S. Kadoya, E. Yonemochi, and K. Terada, Cryobiology and Cryotechnology, 54, (2008). 38) K. Izutsu, S. Kadoya, C. Yomota, T. Kawanishi, E. Yonemochi, and K. Terada, Chem. Pharm. Bull. 57, (2009). 39) K. Izutsu, S. Kadoya, C. Yomota, T. Kawanishi, E. Yonemochi, and K. Terada, Chem. Pharm. Bull. 57, (2009). 40) S. Kadoya, K. Fujii, K. Izutsu, E. Yonemochi, K. Terada, C. Yomota, and T. Kawanishi, Int. J. Pharmaceutics, , 389 (2010). Katsuhide Terada, Toho University, Faculty of Pharmaceutical Sciences, terada@phar.tohou.ac.jp 53
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