The dehydration behavior and non-isothermal dehydration kinetics of donepezil hydrochloride monohydrate (Form I)

Abstract

Powders of donepezil hydrochloride monohydrate (Form I) underwent isomorphic dehydration, losing 3% w/w water between 90% and 10% relative humidity (RH) without changing its powder X-ray pattern. Below 10% RH, additional dehydration occurred in conjunction with a reversible phase transition between the monohydrate state and a dehydrated state, with a 4.0% w/w loss to 0% RH. A combination of methods was used to understand the structural changes occurring during the desolvation process, including dynamic vapor sorption measurements, thermal analysis and powder X-ray diffraction. Form I showed the characteristics of the channel hydrate, whose non-isothermal dehydration behavior proceeds in two steps: (1) the loss of non-crystalline water adsorbed on the surface, and (2) the loss of one crystalline water in the channel. Dehydrated Form I is structurally similar to the monohydrate Form I. According to the heat of fusion and the crystal density criteria, the two crystal forms belonged to the univariant system, and the anhydrate (Form III) is stable. The dehydration kinetics was achieved from the TG-DTG curves by both the Achar method and the Coats-Redfern method with 15 frequently cited basic kinetic models. The dynamic dehydration processes for steps 1 and 2 were best expressed by the Zhuralev-Lesokin-Tempelman equation, suggesting a three-dimensional diffusion-controlled mechanism.

Keywords

dehydration / thermal analysis / transformation / dehydration kinetics

References

[1] Han J, Gupte S, Suryanarayanan R. Applications of pressure differential scanning calorimetry in the study of pharmaceutical hydrates. II. Ampicillin trihydrate. International Journal of Pharmaceutics, 1998, 170(1): 63–72

[2] Krzyzaniak J F, Williams G R, Ni N. Identification of phase boundaries in anhydrate/hydrate systems. Journal of Pharmaceutical Sciences, 2007, 96(5): 1270–1281

[3] Khankari R K, Grant D J W. Pharmaceutical hydrates. Thermochimica Acta, 1995, 248(0): 61–79

[4] Wang S L, Wong Y C, Cheng W T, Lin S Y. A continuous process for solid-state dehydration, amorphization and recrystallization of metoclopramide HCL monohydrate studied by simultaneous DSC-FTIR microspectroscopy. Journal of Thermal Analysis and Calorimetry, 2011, 104(1): 261–264

[5] Byrn S R, Xu W, Newman A W. Chemical reactivity in solid-state pharmaceuticals: formulation implications. Advanced Drug Delivery Reviews, 2001, 48(1): 115–136

[6] Garnier S, Petit S, Coquerel G. Dehydration mechanism and crystallisation behaviour of lactose. Journal of Thermal Analysis and Calorimetry, 2002, 68(2): 489–502

[7] Legendre B, Baziard-Mouysset G, Anastassiadou M, Leger J M, Payard A. Polymorphic study of 2-(2-benzofuryl) Delta-2 imidazoline. Journal of Thermal Analysis and Calorimetry, 2001, 66(2): 659–673

[8] Willart J F, Descamps M. Solid State Amorphization of Pharmaceuticals. Molecular Pharmaceutics, 2008, 5(6): 905–920

[9] Byrn S R, Pfeiffer R R, Stephenson G, Grant D J W, Gleason W B. Solid-State Pharmaceutical Chemistry. Chemistry of Materials, 1994, 6(8): 1148–1158

[10] Vippagunta S R, Brittain H G, Grant D J W. Crystalline solids. Advanced Drug Delivery Reviews, 2001, 48(1): 3–26

[11] Stephenson G A, Groleau E G, Kleemann R L, Xu W, Rigsbee D R. Formation of isomorphic desolvates: Creating a molecular vacuum. Journal of Pharmaceutical Sciences, 1998, 87(5): 536–542

[12] Stephenson G A, Stowell J G, Toma P H, Pfeiffer R R, Byrn S R. Solid-state investigations of erythromycin A dihydrate: structure, NMR spectroscopy, and hygroscopicity. Journal of Pharmaceutical Sciences, 1997, 86(11): 1239–1244

[13] Vogt F G, Brum J, Katrincic L M, Flach A, Socha J M, Goodman R M, Haltiwanger R C. Physical, crystallographic, and spectroscopic characterization of a crystalline pharmaceutical hydrate: Understanding the role of water. Crystal Growth & Design, 2006, 6(10): 2333–2354

[14] Bauer J F, Dziki W, Quick J E. Role of an isomorphic desolvate in dissolution failures of an erythromycin tablet formulation. Journal of Pharmaceutical Sciences, 1999, 88(11): 1222–1227

[15] Te R L, Griesser U J, Morris K R, Byrn S R, Stowell J G. X-ray Diffraction and Solid-State NMR Investigation of the Single-Crystal to Single-Crystal Dehydration of Thiamine Hydrochloride Monohydrate. Crystal Growth & Design, 2003, 3(6): 997–1004

[16] Abu Bakar M R, Nagy Z K, Rielly C D. A combined approach of differential scanning calorimetry and hot-stage microscopy with image analysis in the investigation of sulfathiazole polymorphism. Journal of Thermal Analysis and Calorimetry, 2010, 99(2): 609–619

[17] Kumar S, Chawla G, Sobhia M E, Bansal A K. Characterization of solid-state forms of mebendazole. Die Pharmazie, 2008, 63(2): 136–143

[18] Murdande S B, Pikal M J, Shanker R M, Bogner R H. Solubility Advantage of Amorphous Pharmaceuticals: I. A Thermodynamic Analysis. Journal of Pharmaceutical Sciences, 2010, 99(3): 1254–1264

[19] Sugimoto H, Iimura Y, Yamanishi Y, Yamatsu K. Synthesis and Structure-Activity Relationships of Acetylcholinesterase Inhibitors: 1-Benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine Hydrochloride and Related Compounds. Journal of Medicinal Chemistry, 1995, 38(24): 4821–4829

[20] Sugimoto H, Ogura H, Arai Y, Iimura Y, Yamanishi Y. Research and Development of Donepezil Hydrochloride, a New Type of Acetylcholinesterase Inhibitor. Japanese Journal of Pharmacology, 2002, 89(1): 7–20

[21] Rogers Sl D R S M R C F L T, Donepezil improves cognition and global function in alzheimer disease: A 15-week, double-blind, placebo-controlled study. Archives of Internal Medicine, 1998, 158(9): 1021–1031

[22] Mihara M, Ohnishi A, Tomono Y, Hasegawa J, Shimamura Y, Yamazaki K, Morishita N. Pharmacokinetics of E2020, a new compound for Alzheimer's disease, in healthy male volunteers. International Journal of Clinical Pharmacology, Therapy, and Toxicology, 1993, 31(5): 223–229

[23] Doody R S. Clinical benefits of a new piperidine-class AChE inhibitor. European Neuropsychopharmacology, 1999, 9, Supplement 2(0): S69–S77

[24] Málek J. The kinetic analysis of non-isothermal data. Thermochimica Acta, 1992, 200(0): 257–269

[25] Narahari Achar B N, Bridley G W, Sharp J H. Thermal decomposition kinetics of some new unsaturated polyesters, in: Proc. Int. Clay Conf., Jerusalem, 1966, 67

[26] Coats A W, Redfern J P. Kinetic Parameters from Thermogravimetric Data. Nature, 1964, 201(4914): 68–69

[27] Mumtaz H S, Hounslow M J, Seaton N A, Paterson W R. Orthokinetic Aggregation During Precipitation: A Computational Model for Calcium Oxalate Monohydrate. Chemical Engineering Research & Design, 1997, 75(2): 152–159

[28] Han J, Suryanarayanan R. Influence of Environmental Conditions on the Kinetics and Mechanism of Dehydration of Carbamazepine Dihydrate. Pharmaceutical Development and Technology, 1998, 3(4): 587–596

[29] Zhu H, Xu J, Varlashkin P, Long S, Kidd C. Dehydration, hydration behavior, and structural analysis of fenoprofen calcium. Journal of Pharmaceutical Sciences, 2001, 90(7): 845–859

[30] Malaj L, Censi R, Martino P D. Mechanisms for Dehydration of Three Sodium Naproxen Hydrates. Crystal Growth & Design, 2009, 9(5): 2128–2136

[31] Mane R B, Rode C V. Continuous Dehydration and Hydrogenolysis of Glycerol over Non-Chromium Copper Catalyst: Laboratory-Scale Process Studies. Organic Process Research & Development, 2012, 16(5): 1043–1052

Acknowledgement

The authors are grateful to the financial support of the National Natural Science Foundation of China (Grant No. 21176173), the Tianjin Municipal Natural Science Foundation (11JCZDJC20700), State Key Laboratory of Chemical Engineering of China (SKL-CHE-11B02) and Innovation Foundation of Tianjin University (60302068).

RIGHTS & PERMISSIONS

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg