Cocrystal dissociation in the presence of water: A general approach for identifying stable cocrystal forms

Journal of Pharmaceutical Sciences

Volumn 103, Issue 9, 2014, Pages 2865-2870

  Eddleston, Mark D ^a   Madusanka, Nadeesh ^a   Jones, William ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

cocrystals; hydrates solvates; physical stability; powder X ray diffraction; solid state; solubility

Indexed keywords

CAFFEINE; CARBAMAZEPINE; OXALIC ACID; PIROXICAM; THEOPHYLLINE; WATER; DRUG;

ARTICLE; CRYSTAL STRUCTURE; DISSOCIATION; DRUG IDENTIFICATION; DRUG SCREENING; DRUG STABILITY; HUMIDITY; THERMODYNAMICS; X RAY POWDER DIFFRACTION; CHEMISTRY; CRYSTALLIZATION; MEDICINAL CHEMISTRY; PROCEDURES;

CAFFEINE; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; DRUG STABILITY; HUMIDITY; OXALIC ACID; PHARMACEUTICAL PREPARATIONS; THEOPHYLLINE; THERMODYNAMICS; WATER;

EID: 84906217832     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.24003     Document Type: Article

References (34)

1. Caira MR,. 1992. Molecular complexes of sulfonamides. 2. 1:1 Complexes between drug molecules: Sulfadimidine-acetylsalicylic acid and sulfadimidine-4-aminosalicylic acid. J Crystallogr Spectrosc Res 22 (2): 193-200.
2. Bailey Walsh RD, Bradner MW, Fleischman S, Morales LA, Moulton B, Rodriguez-Hornedo N, Zaworotko MJ,. 2003. Crystal engineering of the composition of pharmaceutical phases. Chem Commun (2): 186-187.
3. Friščic̈ T, Jones W,. 2010. Benefits of cocrystallization in pharmaceutical materials science: An update. J Pharm Pharmacol 62 (11): 1547-1559.
4. Schultheiss N, Newman A,. 2009. Pharmaceutical cocrystals and their physicochemical properties. Cryst Growth Des 9 (6): 2950-2967.
5. Eddleston MD, Thakuria R, Aldous BJ, Jones W,. 2014. An investigation of the causes of cocrystal dissociation at high humidity. J Pharm Sci. (Epub ahead of print). DOI: 10.1002/jps.23865
6. Trask AV, Motherwell WDS, Jones W,. 2005. Pharmaceutical cocrystallization: Engineering a remedy for caffeine hydration. Cryst Growth Des 5 (3): 1013-1021.
7. Trask AV, Motherwell WDS, Jones W,. 2006. Physical stability enhancement of theophylline via cocrystallization. Int J Pharm 320 (1-2): 114-123.
8. Suzuki E, Shirotani K, Tsuda Y, Sekiguchi K,. 1985. Studies on methods of particle size reduction of medicinal compounds. XXIII. Water content and dehydration behavior of crystalline caffeine hydrate. Chem Pharm Bull 33 (11): 5028-5035.
9. Vora KL, Buckton G, Clapham D,. 2004. The use of dynamic vapour sorption and near infra-red spectroscopy (DVS-NIR) to study the crystal transitions of theophylline and the report of a new solid-state transition. Eur J Pharm Sci 22 (2-3): 97-105.
10. Edwards HGM, Lawson E, de Matas M, Shields L, York P,. 1997. Metamorphosis of caffeine hydrate and anhydrous caffeine. J Chem Soc, Perkin Trans 2 (10): 1985-1990.
11. Griesser UJ, Burger A,. 1995. The effect of water vapor pressure on desolvation kinetics of caffeine 4/5-hydrate. Int J Pharm 120 (1): 83-93.
12. Seddon KR, Zaworotko M,. 1999. Crystal engineering: Design and application of functional solids. Dordrecht, The Netherlands: Kluwer Academic Publishers.
13. Brychczynska M, Davey RJ, Pidcock E,. 2008. A study of methanol solvates using the Cambridge structural database. New J Chem 32 (10): 1754-1760.
14. van de Streek J, Motherwell S,. 2007. New software for searching the Cambridge Structural Database for solvated and unsolvated crystal structures applied to hydrates. CrystEngComm 9 (1): 55-64.
15. Desiraju GR,. 1991. Hydration in organic crystals: Prediction from molecular structure. J Chem Soc, Chem Commun (6): 426-428.
16. Khankari RK, Grant DJW,. 1995. Pharmaceutical hydrates. Thermochim Acta 248: 61-79.
17. Pudipeddi M, Serajuddin ATM,. 2005. Trends in solubility of polymorphs. J Pharm Sci 94 (5): 929-939.
18. Byrn S, Pfeiffer R, Ganey M, Hoiberg C, Poochikian G,. 1995. Pharmaceutical solids: A strategic approach to regulatory considerations. Pharm Res 12 (7): 945-954.
19. Vippagunta SR, Brittain HG, Grant DJ,. 2001. Crystalline solids. Adv Drug Deliv Rev 48 (1): 3-26.
20. Morris KR,. 1999. Structural aspects of hydrates and solvates. Drugs and the pharmaceutical sciences. New York: Dekker, pp 125-181.
21. Vogt FG, Dell'Orco PC, Diederich AM, Su Q, Wood JL, Zuber GE, Katrincic LM, Mueller RL, Busby DJ, DeBrosse CW,. 2006. A study of variable hydration states in topotecan hydrochloride. J Pharm Biomed Anal 40 (5): 1080-1088.
22. Childs SL, Rodriguez-Hornedo N, Reddy LS, Jayasankar A, Maheshwari C, McCausland L, Shipplett R, Stahly BC,. 2008. Screening strategies based on solubility and solution composition generate pharmaceutically acceptable cocrystals of carbamazepine. CrystEngComm 10 (7): 856-864.
23. Eddleston MD, Patel B, Day GM, Jones W,. 2013. Cocrystallization by freeze-drying: Preparation of novel multicomponent crystal forms. Cryst Growth Des 13 (10): 4599-4606.
24. Madusanka N, Eddleston MD, Arhangelskis M, Jones W,. 2014. Polymorphs, hydrates and solvates of a co-crystal of caffeine with anthranilic acid. Acta Crystallogr B 70 (1): 72-80.
25. Childs SL, Stahly GP, Park A,. 2007. The salt-cocrystal continuum: The influence of crystal structure on ionization state. Mol Pharm 4 (3): 323-338.
26. Schultheiss N, Roe M, Boerrigter SXM,. 2011. Cocrystals of nutraceutical p-coumaric acid with caffeine and theophylline: Polymorphism and solid-state stability explored in detail using their crystal graphs. CrystEngComm 13 (2): 611-619.
27. Vishweshwar P, McMahon JA, Oliveira M, Peterson ML, Zaworotko MJ,. 2005. The predictably elusive Form II of aspirin. J Am Chem Soc 127 (48): 16802-16803.
28. Eddleston MD, Lloyd GO, Jones W,. 2012. Cocrystal dissociation and molecular demixing in the solid state. Chem Commun 48 (65): 8075-8077.
29. Chiarella RA, Davey RJ, Peterson ML,. 2007. Making co-crystals-The utility of ternary phase diagrams. Cryst Growth Des 7 (7): 1223-1226.
30. Jayasankar A, Reddy LS, Bethune SJ, Rodriguez-Hornedo N,. 2009. Role of cocrystal and solution chemistry on the formation and stability of cocrystals with different stoichiometry. Cryst Growth Des 9 (2): 889-897.
31. Yalkowsky SH, He Y,. 2003. Handbook of aqueous solubility data. Boca Raton, Florida: CRC Press LLC, pp 1512.
32. Zhu H, Yuen C, Grant DJW,. 1996. Influence of water activity in organic solvent + water mixtures on the nature of the crystallizing drug phase. 1. Theophylline. Int J Pharm 135 (1-2): 151-160.
33. Variankaval N, Lee C, Xu J, Calabria R, Tsou N, Ball R,. 2007. Water activity-mediated control of crystalline phases of an active pharmaceutical ingredient. Org Process Res Dev 11 (2): 229-236.
34. Qiu Y, Chen Y, Zhang GGZ,. 2009. Developing solid oral dosage forms: Pharmaceutical theory and practise.: Academic Press, Burlington, MA pp 943.