Effect of position isomerism on the formation and physicochemical properties of pharmaceutical co-crystals

Journal of Pharmaceutical Sciences

Volumn 99, Issue 1, 2010, Pages 246-254

  Liao, Xiangmin ^a   Gautam, Mohan ^b   Grill, Andreas ^a   Zhu, Haijian Jim ^a  

^a FOREST RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

Co crystal; Dihydroxybenzoic acid; Piracetam; Position isomer

Indexed keywords

ACETONITRILE; ALPHA RESORCYLIC ACID; CARBOXYLIC ACID; HYDROXYL GROUP; PIRACETAM;

ARTICLE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG STRUCTURE; FOURIER TRANSFORMATION; HYDROGEN BOND; ISOMERISM; MELTING POINT; PHYSICAL CHEMISTRY; X RAY POWDER DIFFRACTION;

EID: 73949143485     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21824     Document Type: Article

References (16)

1. Vishweshwar P, McMahon JA, Bis JA, Zaworotko MJ. 2006. Pharmaceutical co-crystals. J Pharm Sci 95:499-516.
2. Fleischman SG, Kuduva SS, McMahon JA, Moulton B, Bailey Walsh RD, Rodriguez-Hornedo N, Zaworotko MJ. 2003. Crystal engineering of the composition of pharmaceutical phases: Multiple-component crystalline solids involving carbamazepine. Cryst Growth Des 3:909-919.
3. Remenar JF, Morissette SL, Peterson ML, Moulton B, MacPhee JM, Guzman HR, Almarsson O. 2003. Crystal engineering of novel cocrystals of a triazole drug with 1,4-dicarboxylic acids. J Am Chem Soc 125:8456-8457.
4. Trask AV, Motherwell WDS, Jones W. 2005. Pharmaceutical cocrystallization: Engineering a remedy for caffeine hydration. Cryst Growth Des 5:1013-1021.
5. Trask AV, Motherwell WDS, Jones W. 2006. Physical stability enhancement of theophylline via cocrystallization. Int J Pharm 320:114-123.
6. McNamara DP, Childs SL, Giordano J, Iarriccio A, Cassidy J, Shet MS, Mannion R, O'Donnell E, Park A. 2006. Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API. Pharm Res 23:1888-1897.
7. Sun CC, Hou H. 2008. Improving mechanical properties of caffeine and methyl gallate crystals by cocrystallization. Cryst Growth Des 8:1575-1579.
8. Takata N, Shiraki K, Takano R, Hayashi Y, Terada K. 2008. Cocrystal screening of stanolone and mestanolone using slurry crystallization. Cryst Growth Des 8:3032-3037.
9. Winblad B. 2005. Piracetam: A review of pharmacological properties and clinical uses. CNS Drug Rev 11:169-182.
10. Vishweshwar P, McMahon JA, Peterson ML, Hickey MB, Shattock TR, Zaworotko MJ. 2005. Crystal engineering of pharmaceutical co-crystals from polymorphic active pharmaceutical ingredients. Chem Commun 4601-4603.
11. Abraham MH, Dearden JC, Bresnen GM. 2006. Hydrogen bonding, steric effects and thermodynamics of partitioning. J Phys Org Chem 19:242-248.
12. Dearden JC, BresnenGM. 2005. Thermodynamics of water-octanol and water-cyclohexane partitioning of some aromatic compounds. Int J Mol Sci 6:119-129.
13. Rozenberg M, Shoham G. 2007. FTIR spectra of solid poly-L-lysine in the stretching NH mode range. Biophys Chem 125:166-171.
14. Dalterio R, Huang XS, Yu K-L. 2007. Infrared and nuclear magnetic resonance spectroscopic study of secondary amide hydrogen bonding in benzoyl PABA derivatives (retinoids). Appl Spectrosc 61:603-607.
15. Iogansen AV. 1999. Direct proportionality of the hydrogen bonding energy and the intensification of the stretching n(XH) vibration in infrared spectra. Spectrochim Acta Part A 55A:1585-1612.
16. Simperler A, Watt SW, Bonnet PA, Jones W, Motherwell WDS. 2006. Correlation of melting point of inositols with hydrogen bonding patterns. CrystEngComm 8:589-600.