Polymorphism in cocrystals: a review and assessment of its significance

被引:253
作者
Aitipamula, Srinivasulu [1 ]
Chow, Pui Shan [1 ]
Tan, Reginald B. H. [1 ,2 ]
机构
[1] ASTAR, Inst Chem & Engn Sci, Singapore 627833, Singapore
[2] Natl Univ Singapore, Dept Chem & Biomol Engn, Singapore 117576, Singapore
来源
CRYSTENGCOMM | 2014年 / 16卷 / 17期
关键词
DISSOLVING EUTECTIC COMPOSITIONS; CRYSTAL-STRUCTURE PREDICTION; MULTIPLE-COMPONENT CRYSTALS; ACID CO-CRYSTALS; PHARMACEUTICAL COCRYSTALS; CONFORMATIONAL POLYMORPHISM; PHYSICOCHEMICAL PROPERTIES; TAUTOMERIC POLYMORPHISM; CONCOMITANT POLYMORPHS; 4-HYDROXYBENZOIC ACID;
D O I
10.1039/c3ce42008f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cocrystals have gained much interest in recent years owing to their potential to improve the physicochemical properties of the parent compounds. It was once thought that cocrystals could be a means to prevent polymorphism but many recent examples of cocrystal polymorphism have been discovered and reported. Similar to single component crystals, polymorphs of cocrystals can display significantly different properties. In this contribution, we present a survey of polymorphic cocrystals. The different types of polymorphs, namely synthon, conformational, packing, and tautomeric, are identified and discussed with representative examples. In addition, polymorphs of cocrystals that showed distinct physicochemical properties are highlighted.
引用
收藏
页码:3451 / 3465
页数:15
相关论文
共 154 条
[1]   Building co-crystals with molecular sense and supramolecular sensibility [J].
Aakeröy, CB ;
Salmon, DJ .
CRYSTENGCOMM, 2005, 7 :439-448
[2]   Pyrazinamide cocrystals and the search for polymorphs [J].
Abourahma, Heba ;
Cocuzza, Devon S. ;
Melendez, Jesus ;
Urban, Jennifer M. .
CRYSTENGCOMM, 2011, 13 (21) :6442-6450
[3]   Trimorphs of a pharmaceutical cocrystal involving two active pharmaceutical ingredients: potential relevance to combination drugs [J].
Aitipamula, Srinivasulu ;
Chow, Pui Shan ;
Tan, Reginald B. H. .
CRYSTENGCOMM, 2009, 11 (09) :1823-1827
[4]   Novel solid forms of the anti-tuberculosis drug, Isoniazid: ternary and polymorphic cocrystals [J].
Aitipamula, Srinivasulu ;
Wong, Annie B. H. ;
Chow, Pui Shan ;
Tan, Reginald B. H. .
CRYSTENGCOMM, 2013, 15 (29) :5877-5887
[5]   Polymorphism and phase transformations of a cocrystal of nicotinamide and pimelic acid [J].
Aitipamula, Srinivasulu ;
Wong, Annie B. H. ;
Chow, Pui Shan ;
Tan, Reginald B. H. .
CRYSTENGCOMM, 2012, 14 (23) :8193-8198
[6]   Polymorphs, Salts, and Cocrystals: What's in a Name? [J].
Aitipamula, Srinivasulu ;
Banerjee, Rahul ;
Bansal, Arvind K. ;
Biradha, Kumar ;
Cheney, Miranda L. ;
Choudhury, Angshuman Roy ;
Desiraju, Gautam R. ;
Dikundwar, Amol G. ;
Dubey, Ritesh ;
Duggirala, Nagakiran ;
Ghogale, Preetam P. ;
Ghosh, Soumyajit ;
Goswami, Pramod Kumar ;
Goud, N. Rajesh ;
Jetti, Ram R. K. R. ;
Karpinski, Piotr ;
Kaushik, Poonam ;
Kumar, Dinesh ;
Kumar, Vineet ;
Moulton, Brian ;
Mukherjee, Arijit ;
Mukherjee, Gargi ;
Myerson, Allan S. ;
Puri, Vibha ;
Ramanan, Arunachalam ;
Rajamannar, T. ;
Reddy, C. Malla ;
Rodriguez-Hornedo, Nair ;
Rogers, Robin D. ;
Row, T. N. Guru ;
Sanphui, Palash ;
Shan, Ning ;
Shete, Ganesh ;
Singh, Amit ;
Sun, Changquan C. ;
Swift, Jennifer A. ;
Thaimattam, Ram ;
Thakur, Tejender S. ;
Thaper, Rajesh Kumar ;
Thomas, Sajesh P. ;
Tothadi, Srinu ;
Vangala, Venu R. ;
Variankaval, Narayan ;
Vishweshwar, Peddy ;
Weyna, David R. ;
Zaworotko, Michael J. .
CRYSTAL GROWTH & DESIGN, 2012, 12 (05) :2147-2152
[7]   Co-crystals of caffeine and piracetam with 4-hydroxybenzoic acid: Unravelling the hidden hydrates of 1: 1 co-crystals [J].
Aitipamula, Srinivasulu ;
Chow, Pui Shan ;
Tan, Reginald B. H. .
CRYSTENGCOMM, 2012, 14 (07) :2381-2385
[8]   The solvates of sulfamerazine: structural, thermochemical, and desolvation studies [J].
Aitipamula, Srinivasulu ;
Chow, Pui Shan ;
Tan, Reginald B. H. .
CRYSTENGCOMM, 2012, 14 (02) :691-699
[9]   Conformational and enantiotropic polymorphism of a 1: 1 cocrystal involving ethenzamide and ethylmalonic acid [J].
Aitipamula, Srinivasulu ;
Chow, Pui Shan ;
Tan, Reginald B. H. .
CRYSTENGCOMM, 2010, 12 (11) :3691-3697
[10]   Polymorphs and Solvates of a Cocrystal Involving an Analgesic Drug, Ethenzamide, and 3,5-Dinitrobenzoic Acid [J].
Aitipamula, Srinivasulu ;
Chow, Pui Shan ;
Tan, Reginald B. H. .
CRYSTAL GROWTH & DESIGN, 2010, 10 (05) :2229-2238