Investigation of the formation process of two piracetam cocrystals during grinding

Pharmaceutics

Volumn 3, Issue 4, 2011, Pages 706-722

  Rehder, Sönke ^a   Klukkert, Marten ^a,b   Löbmann, Korbinian A M ^b   Strachan, Clare J ^b   Sakmann, Albrecht ^a   Gordon, Keith ^b   Rades, Thomas ^b   Leopold, Claudia S ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b UNIVERSITY OF OTAGO   (New Zealand)

Author keywords

Chemometrics; Cocrystal; Formation kinetics; Grinding; Piracetam

Indexed keywords

CITRIC ACID; PIRACETAM; TARTARIC ACID;

ARTICLE; CONTROLLED STUDY; CRYSTALLIZATION; DRUG STRUCTURE; DRY GRINDING; GRINDING; INTERMETHOD COMPARISON; LIQUID ASSISTED GRINDING; PRINCIPAL COMPONENT ANALYSIS; RAMAN SPECTROMETRY; TABLET MANUFACTURE; X RAY POWDER DIFFRACTION;

EID: 84255204806     PISSN: None     EISSN: 19994923     Source Type: Journal    
DOI: 10.3390/pharmaceutics3040706     Document Type: Article

References (26)

1. Shan, N.; Zaworotko, M.J. The role of cocrystals in pharmaceutical science. Drug Discov. Today 2008, 13, 440-446.
2. Fleischman, S.G.; Kuduva, S.S.; McMahon, J.A.; Moulton, B.; Bailey Walsh, R.D.; Rodriguez-Hornedo, N.; Zaworotko, M.J. Crystal engineering of the composition of pharmaceutical phases: multiple-component crystalline solids involving carbamazepine Cryst. Growth Des. 2003, 3, 909-919.
3. Trask, A.V.; Motherwell, W.D.S.; Jones, W. Pharmaceutical cocrystallization: Engineering a remedy for caffeine hydration. Cryst. Growth Des. 2005, 5, 1013-1021.
4. Vangala, V.R.; Chow, P.S.; Tan, R.B.H. Characterization, physicochemical and photo-stability of a co-crystal involving an antibiotic drug, nitrofurantoin, and 4-hydroxybenzoic acid. CrystEngComm 2011, 13, 759-762.
5. Viertelhaus, M.; Hilfiker, R.; Blatter, F.; Neuburger, M. Piracetam co-crystals with OH-group functionalized carboxylic acids. Cryst. Growth Des. 2009, 9, 2220-2228.
6. Remenar, J.F.; Morissette, S.L.; Peterson, M.L.; Moulton, B.; MacPhee, J.M.; Guzmán, H.R.; Almarsson, Ö. Crystal engineering of novel cocrystals of a triazole drug with 1,4-dicarboxylic acids. J. Am. Chem. Soc. 2003, 125, 8456-8457.
7. Hickey, M.B.; Peterson, M.L.; Scoppettuolo, L.A.; Morrissette, S.L.; Vetter, A.; Guzmán, H.; Remenar, J.F.; Zhang, Z.; Tawa, M.D.; Haley, S.; Zaworotko, M.J.; Almarsson, Ö. Performance comparison of a co-crystal of carbamazepine with marketed product. Eur. J. Pharm. Biopharm. 2007, 67, 112-119.
8. Blagden, N.; Berry, D.J.; Parkin, A.; Javed, H.; Ibrahim, A.; Gavan, P.T.; De Matos, L.L.; Seaton, C.C. Current directions in co-crystal growth. New J. Chem. 2008, 32, 1659-1672.
9. Fabbiani, F.P.A.; Allan, D.R.; David, W.I.F.; Davidson, A.J.; Lennie, A.R.; Parsons, S.; Pulham, C.R.; Warren, J.E. High-pressure studies of pharmaceuticals: an exploration of the behavior of piracetam. Cryst. Growth Des. 2007, 7, 1115-1124.
10. Fabbiani, F.P.A.; Allan, D.R.; Parsons, S.; Pulham, C.R. An exploration of the polymorphism of piracetam using high pressure. CrystEngComm 2005, 7, 179-186.
11. Kuhnert-Brandstätter, M.; Burger, A.; Völlenklee, R. Stability behavior of piracetam polymorphs. Sci. Pharm. 1994, 62, 307-316.
12. Aakeröy, C.B. Crystal engineering: strategies and architectures. Acta Crystallogr. B 1997, 53, 569-586.
13. Vishweshwar, P.; McMahon, J.A.; Peterson, M.L.; Hickey, M.B.; Shattock, T.R.; Zaworotko, M.J. Crystal engineering of pharmaceutical co-crystals from polymorphic active pharmaceutical ingredients. Chem. Commun. 2005, 4601-4603.
14. Liao, X.; Gautam, M.; Grill, A.; Zhu, H.J. Effect of position isomerism on the formation and physicochemical properties of pharmaceutical co-crystals. J. Pharm. Sci. 2010, 99, 246-254.
15. Chieng, N.; Hubert, M.; Saville, D.; Rades, T.; Aaltonen, J. Formation kinetics and stability of carbamazepine-nicotinamide cocrystals prepared by mechanical activation. Cryst. Growth Des. 2009, 9, 2377-2386.
16. Friščić, T.; Jones, W. Recent advances in understanding the mechanism of cocrystal formation via grinding. Cryst. Growth Des. 2009, 9, 1621-1637.
17. Jayasankar, A.; Somwangthanaroj, A.; Shao, Z.J.; Rodríguez-Hornedo, N. Cocrystal formation during cogrinding and storage is mediated by amorphous phase. Pharm. Res. 2006, 23, 2381-2392.
18. Shan, N.; Toda, F.; Jones, W. Mechanochemistry and co-crystal formation: effect of solvent on reaction kinetics. Chem. Comm. 2002, 2372-2373.
19. Friščić, T.; Childs, S.L.; Rizvi, S.A.A.; Jones, W. The role of solvent in mechanochemical and sonochemical cocrystal formation: a solubility-based approach for predicting cocrystallization outcome. CrystEngComm 2009, 11, 418-426.
20. Allesø, M.; Velaga, S.; Alhalaweh, A.; Cornett, C.; Rasmussen, M.A.; van den Berg, F.; Lopez de Diego, H.; Rantanen, J. Near-infrared spectroscopy for cocrystal screening. A comparative study with Raman spectroscopy. Anal. Chem. 2008, 80, 7755-7764.
21. Shattock, T.R.; Arora, K.K.; Vishweshwar, P.; Zaworotko, M.J. Hierarchy of supramolecular synthons: persistent carboxylic acid pyridine hydrogen bonds in cocrystals that also contain a hydroxyl moiety. Cryst. Growth Des. 2008, 8, 4533-4545.
22. Allen, F.H. The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Cryst. 2002, 58, 380-388.
23. Bruno, I.J.; Cole, J.C.; Edgington, P.R.; Kessler, M.; Macrae, C.F.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P.A. New software for searching the Cambridge Structural Database and visualising crystal structures. Acta Cryst. 2002, 58, 389-397.
24. Macrae, C.F.; Bruno, I.J.; Chisholm, J.A.; Edgington, P.R.; McCabe, P.; Pidcock, E.; Rodriguez- Monge, L.; Taylor, R.; van de Streek, J.; Wood, P.A. Mercury CSD 2.0-New features for the visualization and investigation of crystal structures. J. Appl. Cryst. 2008, 41, 466-470.
25. Maher, A.; Croker, D.; Rasmuson, A.C.; Hodnett, B.K. Solubility of form III piracetam in a range of solvents. J. Chem. Eng. Data 2010, 55, 5314-5318.
26. Crowley, K.J.; Zografi, G. Cryogenic grinding of indomethacin polymorphs and solvates: assessment of amorphous phase formation and amorphous phase physical stability. J. Pharm. Sci. 2002, 91, 492-507.