RESEARCH ARTICLE

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

  • Tiantian LIU 1 ,
  • Yuanyuan RAN 1 ,
  • Bochao WANG 1 ,
  • Weibing DONG 2 ,
  • Songgu WU 1 ,
  • Junbo GONG , 1
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  • 1. The National Engineering Research Center of Industrial Crystallization Technology, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China
  • 2. Tianjin Key Laboratory for Modern Drug Delivery and High Efficiency, Tianjin University, Tianjin 300072, China

Received date: 13 May 2013

Accepted date: 10 Aug 2013

Published date: 05 Mar 2014

Copyright

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg

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.

Cite this article

Tiantian LIU , Yuanyuan RAN , Bochao WANG , Weibing DONG , Songgu WU , Junbo GONG . The dehydration behavior and non-isothermal dehydration kinetics of donepezil hydrochloride monohydrate (Form I)[J]. Frontiers of Chemical Science and Engineering, 2014 , 8(1) : 55 -63 . DOI: 10.1007/s11705-013-1352-3

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).
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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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