Identification and characterization of stoichiometric and nonstoichiometric hydrate forms of paroxetine HCl: Reversible changes in crystal dimensions as a function of water absorption

Molecular Pharmaceutics

Volumn 9, Issue 12, 2012, Pages 3515-3525

  Pina, M Fátima ^a,b,c   Pinto, João F ^c   Sousa, João J ^a   Fábián, László ^b   Zhao, Min ^b   Craig, Duncan Q M ^b  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^c RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

Author keywords

hydrate; nonstoichiometric; paroxetine HCl; solid state; stoichiometric

Indexed keywords

PAROXETINE;

ARTICLE; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG SCREENING; HEATING; HUMIDITY; HYDRATION; INFRARED SPECTROSCOPY; MOLECULAR MODEL; NEAR INFRARED REFLECTANCE SPECTROSCOPY; PRIORITY JOURNAL; SIMULATION; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION; TEMPERATURE; THERMOGRAVIMETRY; TITRIMETRY; WATER ABSORPTION; WATER CONTENT; X RAY POWDER DIFFRACTION;

ANTIDEPRESSIVE AGENTS, SECOND-GENERATION; CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLIZATION; DRUG STABILITY; HUMIDITY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PAROXETINE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; WATER; X-RAY DIFFRACTION;

EID: 84870486864     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp3003573     Document Type: Article

References (35)

1. Koradia, V.; Fontelonga de Lemos, A. F.; Allesø, M.; Lopez de Diego, H.; Ringkjøbing-Elema, M.; Müllertz, A.; Rantanen, J. Phase transformations of amlodipine besylate solid forms J. Pharm. Sci. 2011, 100, 2896-2910
2. Giron, D.; Goldbronn, C.; Mutz, M.; Pfeffer, S.; Piechon, P.; Schwab, P. Solid State Characterizations of Pharmaceutical Hydrates J. Therm. Anal. Calorim. 2002, 68, 453-465 (Pubitemid 34614446)
3. Griesser, U. J. The Importance of Solvates; WILEY-VCH: Germany, 2006; pp 211-230.
4. Khankari, R. K.; Grant, D. J. W. Pharmaceutical hydrates Thermochim. Acta 1995, 248, 61-79
5. Kobayashi, K.; Kimura, S.; Togawa, E.; Wada, M.; Kuga, S. Crystal transition of paramylon with dehydration and hydration Carbohydr. Polym. 2009, 80, 492-498
6. Vogt, F. G.; DellOrco, P. C.; Diederich, A. M.; Su, Q.; Wood, J. L.; Zuber, G. E.; Katrincic, L. M.; Mueller, R. L.; Busby, D. J.; DeBrosse, C. W. A study of variable hydration states in topotecan hydrochloride J. Pharm. Biomed. Anal. 2006, 40, 1080-1088 (Pubitemid 43247444)
7. Guguta, C.; Meekes, H.; de Gelder, R. Crystal Structure of Aspartame Anhydrate from Powder Diffraction Data. Structural Aspects of the Dehydration Process of Aspartame Cryst. Growth Des. 2006, 6, 2686-2692
8. Stephenson, G. A.; Groleau, E. G.; Kleemann, R. L.; Xu, W.; Rigsbee, D. R. Formation of isomorphic desolvates: Creating a molecular vacuum J. Pharm. Sci. 1998, 87, 536-542 (Pubitemid 28225615)
9. Vippagunta, S. R.; Brittain, H. G.; Grant, D. J. W. Crystalline solids Adv. Drug Delivery Rev. 2001, 48, 3-26 (Pubitemid 32452290)
10. Ahlneck, C.; Zografi, G. The molecular basis of moisture effects on the physical and chemical stability of drugs in the solid state Int. J. Pharm. 1990, 62, 87-95 (Pubitemid 20261777)
11. Reutzel, S. M. Origins of the unusual hygroscopicity observed in LY297802 tartrate J. Pharm. Sci. 1998, 87, 1568-1571 (Pubitemid 28559643)
12. Bourin, M.; Chue, P.; Guillon, Y. Paroxetine: A Review CNS Drug Rev. 2001, 7, 25-47 (Pubitemid 32280682)
13. Barnes, R. D.; Wood-Kaczmar, M. W.; Curzons, A. D.; Lynch, I. R.; Richardson, J. E.; Buxton, P. C. Anti-depressant crystalline paroxetine hydrochloride hemihydrate. Patent US4,721,723, 1988.
14. Buxton, P. C.; Lynch, I. R.; Roe, J. M. Solid-state forms of paroxetine hydrochloride Int. J. Pharm. 1988, 42, 135-143 (Pubitemid 18092101)
15. Ward, N.; Jacewicz, V. W. Paroxetine Hydrochloride Form A or C. Patent US6,133,289, 2000.
16. Coelho, A. TOPAS Academic User Manual. Version 4.1; Australia, 2007.
17. Gale, J. D. GULP: Capabilities and prospects Z. Kristallogr. 2005, 220, 552-554 (Pubitemid 40778239)
18. Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III. DREIDING: A generic force field for molecular simulations J. Phys. Chem. 1990, 94, 8897-8909
19. Jakalian, A.; Jack, D. B.; Bayly, C. I. Fast, efficient generation of high-quality atomic charges. AM1-BCC model: II. Parameterization and validation J. Comput. Chem. 2002, 23, 1623-1641 (Pubitemid 35330860)
20. Craig, D. Q. M.; Reading, M. Thermal Analysis of Pharmaceuticals; CRC Press Taylor and Francis Group: New York, 2007; pp 193-219.
21. Nakamoto, K.; Margoshes, M.; Rundle, R. E. Stretching frequencies as a function of distances in hydrogen bonds J. Am. Chem. Soc. 1955, 77, 6480-6486
22. Heacock, R. A.; Marion, L. THE INFRARED SPECTRA OF SECONDARY AMINES AND THEIR SALTS Can. J. Chem. 1956, 34, 1782-1795
23. Tang, X. C.; Pikal, M. J.; Taylor, L. S. A spectroscopic investigation of hydrogen bond patterns in crystalline and amorphous phases in dihydropyridine calcium channel blockers Pharm. Res. 2002, 19, 477-483 (Pubitemid 34408948)
24. Stephenson, G. A.; Diseroad, B. A. Structural relationship and desolvation behavior of cromolyn, cefazolin and fenoprofen sodium hydrates Int. J. Pharm. 2000, 198, 167-177 (Pubitemid 30184854)
25. Ahlqvist, M. U. A.; Taylor, L. S. Water dynamics in channel hydrates investigated using H/D exchange Int. J. Pharm. 2002, 241, 253-261 (Pubitemid 34718027)
26. Kumar, L.; Bansal, A. K. Effect of humidity on the hydration behaviour of prazosin hydrochloride polyhydrate: Thermal, sorption and crystallographic study Thermochim. Acta 2011, 525, 206-210
27. Yokota, M.; Uekusa, H.; Ohashi, Y. Structure analyses of two crystal forms of paroxetine hydrochloride Bull. Chem. Soc. Jpn. 1999, 72, 1731-1736 (Pubitemid 29399673)
28. Howard, J. A. K.; Pattison, P.; Chetina, O. Private communication to the Cambridge Crystallographic Data Centre, 2003.
29. Allen, F. H. The Cambridge Structural Database: a quarter of a million crystal structures and rising Acta Crystallogr., Sect. B 2002, 58, 380-388 (Pubitemid 135702674)
30. Redman-Furey, N.; Dicks, M.; Bigalow-Kern, A.; Cambron, R. T.; Lubey, G.; Lester, C.; Vaughn, D. Structural and analytical characterization of three hydrates and an anhydrate form of risedronate J. Pharm. Sci. 2005, 94, 893-911 (Pubitemid 40577321)
31. Cox, J. S. G.; Woodard, G. D.; McCrone, W. C. Solid-state chemistry of cromolyn sodium (disodium cromoglycate) J. Pharm. Sci. 1971, 60, 1458-1465
32. Chen, L. R.; Young, V. G., Jr.; Lechuga-Ballesteros, D.; Grant, D. J. W. Solid-state behavior of cromolyn sodium hydrates J. Pharm. Sci. 1999, 88, 1191-1200 (Pubitemid 29526306)
33. 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 Cryst. Growth Des. 2003, 3, 997-1004 (Pubitemid 37467750)
34. Chakravarty, P.; Berendt, R. T.; Munson, E. J.; Young, V. G.; Govindarajan, R.; Suryanarayanan, R. Insights into the Dehydration Behavior of Thiamine Hydrochloride (Vitamin B(1)) Hydrates: Part I J. Pharm. Sci. 2009, 99, 816-827
35. Chakravarty, P.; Berendt, R. T.; Munson, E. J.; Young, V. G.; Govindarajan, R.; Suryanarayanan, R. Insights Into the Dehydration Behavior of Thiamine Hydrochloride (vitamin B(1)) Hydrates: Part II J. Pharm. Sci. 2009, 99, 1882-1895