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Cocrystal Systems of Pharmaceutical Interest: 2012–2014
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Cocrystal Systems of Pharmaceutical Interest: 2012–2014 Harry G. Brittain Center for Pharmaceutical Physics, Milford, NJ, United States
Contents References
29
Pharmaceutical scientists continue to recognize that one can oftentimes obtain a significant improvement in drug substance properties by simultaneously crystallizing the active ingredient with another substance in a single crystal lattice [1,2]. At present, the field still tends to be dominated by studies of mainly crystallographic interest, although a significant number of these entail work performed on compounds having pharmaceutical interest [3]. Nevertheless, research scientists have begun to take advantage of this structural information in the development of new routes of drug delivery [4]. Given the relatively poor solubility associated with many recently discovered compounds of pharmaceutical interest, it is not surprising that cocrystal systems are receiving ever increasing degrees of attention [5,6]. Developments in the field of pharmaceutical cocrystals have been documented in the form of chronological review articles [7–10]. The continuing rapid growth in the field, and the burgeoning number of compounds that have been cocrystallized, calls for compilations of the studies involved so that future work can continue along new pathways without duplication of the prior art. Accordingly, appropriate publications drawn from the major physical, crystallographic, and pharmaceutical journals are chronicled in the current review of the 2012–2014 literature, being sorted according to the identity of the drug substance involved. This information is contained in Table 1, where the primary sorting has been by compound name and year
Profiles of Drug Substances, Excipients, and Related Methodology ISSN 1871-5125 https://doi.org/10.1016/bs.podrm.2018.11.004
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2019 Elsevier Inc. All rights reserved.
1
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest Compound Year Journal Volume: pages Authors Title
2013 CEC
15: 4816–4822 John R.G. Sander, Dejan-Kresˇimir ‘Masked synthons’ in crystal Bucar, Rodger F. Henry, Brittany engineering: insulated components N. Giangiorgi, Geoff G.Z. Zhang, in acetaminophen cocrystal hydrates and Leonard R. MacGillivray
Acetazolamide
2012 CGD
12: 811–824
Jenniffer I. Arenas-Garcı´a, Dea Herrera-Ruiz, Karina Mondrago´nVa´squez, Hugo Morales-Rojas, and Herbert H€ opfl
Modification of the supramolecular hydrogen-bonding patterns of acetazolamide in the presence of different cocrystal formers: 3:1, 2:1, 1:1, and 1:2 cocrystals from screening with the structural isomers of hydroxybenzoic acids, aminobenzoic acids, hydroxybenzamides, aminobenzamides, nicotinic acids, nicotinamides, and 2,3dihydroxybenzoic acids
Acyclovir
2012 IJP
422: 160–169
Takaaki Masuda, Yasuo Yoshihashi, Etsuo Yonemochi, Kotaro Fujii, Hidehiro Uekusa, and Katsuhide Terada
Cocrystallization and amorphization induced by drug–excipient interaction improves the physical properties of acyclovir
Acyclovir
2013 CEC
15: 6457–6460 Yan Yan, Jia-Mei Chen, and Tong-Bu Lu
Simultaneously enhancing the solubility and permeability of acyclovir by crystal engineering approach
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Acetaminophen
2013 JPS
102: 4079–4086
Giovanna Bruni, Mariarosa Maietta, Lauretta Maggi, Piercarlo Mustarelli, Chiara Ferrara, Vittorio Berbenni, Chiara Milanese, Alessandro Girella, and AmedeoMarini
Adenine
2013 CGD
13: 1464–1472 Laura J. Thompson, Norhanida Elias, Louise Male, and Maryjane Tremayne
Agomelatine
2012 CGD
12: 2226–2233 Yan Yan, Jia-Mei Chen, Na Geng, Improving the solubility of and Tong-Bu Lu agomelatine via cocrystals
Aminosalicylic acid
2013 CGD
13: 360–366
Azelnidipine
2013 CEC
15: 3885–3891 Weiguang Lian, Yulong Lin, Min Crystal engineering approach to Wang, Caiqin Yang, and Jing Wang produce complex of azelnidipine with maleic acid
Baicalein
2012 AC
C68: 262–265 Michal Sowa, Katarzyna Slepokura, A 1:1 cocrystal of baicalein with and Ewa Matczak-Jon nicotinamide
Baicalein
2014 JPS
103: 2330–2337
Pramod Kumar Goswami, Ram Thaimattam, and Arunachalam Ramanan
Yanting Huang, Bowen Zhang, Yuan Gao, Jianjun Zhang, and Limin Shi
Preparation and physicochemical characterization of acyclovir cocrystals with improved dissolution properties Supramolecular behavior of adenine with succinic, fumaric, and maleic acids: tautomerism, cocrystallization, salt formation, and solvation
Multiple crystal forms of p-aminosalicylic acid: salts, salt cocrystal hydrate, cocrystals, and cocrystal polymorphs
Baicalein–nicotinamide cocrystal with enhanced solubility, dissolution, and oral bioavailability Continued
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Acyclovir
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2014 CEC
16: 5765–5768 M. Gryl, T. Seidler, K. Stadnicka, I. The crystal structure and optical Matulkova´, I. Nemec, N. properties of a pharmaceutical Tesarova´c, and P. Nemec cocrystal—the case of the melamine–barbital addition compound
Barbituric acid
2013 CEC
15: 7598–7605 Michele R. Chierotti, Katia Gaglioti, Roberto Gobetto, Dario Braga, Fabrizia Grepioni, and Lucia Maini
From molecular crystals to salt cocrystals of barbituric acid via the carbonate ion and an improvement of the solid state properties
Brivaracetam
2014 CEC
16: 5887–5896 Fabrizia Grepioni, Johan Wouters, Dario Braga, Saverio Nanna, Baptiste Fours, Gerard Coquerel, Geraldine Longfils, Sandrine Rome, Luc Aertse, and Luc Quere
Ionic cocrystals of racetams: solidstate properties enhancement of neutral active pharmaceutical ingredients via addition of Mg2+ and Ca2+ chlorides
Caffeine
2012 CGD
12: 1520–1530 Tom Leyssens, Geraldine Springuel, Importance of solvent selection for Riccardo Montis, Nadine Candoni, stoichiometrically diverse cocrystal and Stephane Veesler systems: caffeine/maleic acid 1:1 and 2:1 cocrystals
Caffeine
2012 CEC
14: 2444–2453 Soumyajit Ghosha and C. Malla Reddy
Cocrystals of caffeine with substituted nitroanilines and nitrobenzoic acids: structure–mechanical property and thermal studies
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Barbital
2012 CEC
14: 2381–2385 Srinivasulu Aitipamula, Pui Shan Chow, and Reginald B.H. Tan
Cocrystals of caffeine and piracetam with 4-hydroxybenzoic acid: unravelling the hidden hydrates of 1:1 cocrystals
Caffeine
2013 CGD
13: 4435–4441 Soumyajit Ghosh, Arobendo Mondal, M.S.R.N. Kiran, U. Ramamurty, and C. Malla Reddy
The role of weak interactions in the phase transition and distinct mechanical behavior of two structurally similar caffeine cocrystal polymorphs studied by nanoindentation
Caffeine
2013 CEC
15: 3705–3710 Sudhir Pagire, Sachin Korde, Rohan Ambardekar, Shivprasad Deshmukh, Radha Charan Dash, Ravindra Dhumal, and Anant Paradkar
Microwave assisted synthesis of caffeine/maleic acid cocrystals: the role of the dielectric and physicochemical properties of the solvent
Caffeine
2013 Chemical 4: 4417–4425 Science
Caffeine
2014 CGD
Dejan-Kresˇimir Bucar, Graeme M. Day, Ivan Halasz, Geoff G.Z. Zhang, John R.G. Sander, David G. Reid, Leonard R. MacGillivray, Melinda J. Duer, and William Jones
The curious case of (caffeine) (benzoic acid): how heteronuclear seeding allowed the formation of an elusive cocrystal
14: 3949–3957 Zai Qun Yu, Pui Shan Chow, and Design space for polymorphic Reginald B.H. Tan co-crystallization: incorporating process model uncertainty and operational variability Continued
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Caffeine
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2014 CEC
16: 8272–8278 Franziska Fischer, Gudrun Scholz, Sigrid Benemann, Klaus Rademannb, and Franziska Emmerling
Evaluation of the formation pathways of cocrystal polymorphs in liquid-assisted syntheses
Caffeine
2014 CEC
16: 9603–9611 T. Leyssens, N. Tumanova, K. Robeyns, N. Candonib, and S. Veesler
Solution cocrystallization, an effective tool to explore the variety of cocrystal systems: caffeine/ dicarboxylic acid cocrystals
Caffeine
2014 AC
B70: 72–80
Nadeesh Madusanka, Mark D. Polymorphs, hydrates and solvates of Eddleston, Mihails Arhangelskis, and a cocrystal of caffeine with William Jones anthranilic acid
Caffeine
2014 JPS
103: 2859–2864
Mark D. Eddleston, Ranjit Thakuria, Barry J. Aldous, and William Jones
An investigation of the causes of cocrystal dissociation at high humidity
Caffeine
2014 JPS
103: 2865–2870
Mark D. Eddleston, Nadeesh Madusanka, and William Jones
Cocrystal dissociation in the presence of water: a general approach for identifying stable cocrystal forms
Carbamazepine
2013 CGD
13: 4162–4167 Sudhir K. Pagire, Sachin A. Korde, Spherical crystallization of Benjamin R. Whiteside, John carbamazepine/saccharin cocrystals: Kendrick, and Anant Paradkar selective agglomeration and purification through surface interactions
ARTICLE IN PRESS
Caffeine
Carbamazepine
2013 CEC
15: 3862–3873 Syarifah Abd Rahim, Robert B. A comparative assessment of the Hammond, Ahmad Y. Sheikh, and influence of different crystallization Kevin J. Roberts screening methodologies on the solid forms of carbamazepine cocrystals
Carbamazepine
2013 IJP
450: 311–322
Carbamazepine
2014 CGD
14: 6508–6513 Amanda R. Buist and Alan R. Kennedy
Carbamazepine
2014 CGD
14: 189–198
Carbamazepine
2014 CEC
16: 3573–3583 Hiren G. Moradiya, Muhammad T. Continuous cocrystallisation of Islam, Sheelagh Halsey, Mohammed carbamazepine and trans-cinnamic Maniruzzaman, Babur Z. acid via melt extrusion processing Chowdhry, Martin J. Snowdena, and D. Douroumis
Carbamazepine
2014 JPS
*****103: 2904–2910
Anti-solvent cocrystallization of carbamazepine and saccharin Ionic cocrystals of pharmaceutical compounds: sodium complexes of carbamazepine
Hiren Moradiya, Muhammad T. Continuous cocrystallization for Islam, Grahame R. Woollam, Ian J. dissolution rate optimization of a Slipper, Sheelagh Halsey, Martin J. poorly water-soluble drug Snowden, and D. Douroumis
Kevin Boksa, Andrew Otte, and Rodolfo Pinal
Matrix-assisted cocrystallization (MAC) simultaneous production and formulation of pharmaceutical cocrystals by hot-melt extrusion Continued
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In-Chun Wang, Min-Jeong Lee, Sang-Jun Sim, Woo-Sik Kim, and Guang J. Choi
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
Carbamazepine
2014 EJPS
62: 251–257
Shashank P. Patil, Sameer R. Modi, Generation of 1:1 carbamazepine: and Arvind K. Bansal nicotinamide cocrystals by spray drying
Carbamazepine
2014 CPB
62: 1125–1130 Yutaka Inoue, Sayuri Sato, Chisa Yamamoto, Mikio Yamasaki, and Ikuo Kanamo
Carprofen
2012 CEC
Celecoxib
2014 CEC
16: 24–27
Celecoxib
2014 CEC
16: Xiaojuan Wang, Qi Zhang, Linglei Isostructurality in six celecoxib 10,959–10,968 Jiang, Yun Xu, and Xuefeng Mei cocrystals introduced by solvent inclusion
Coumaric acid
2014 CGD
14: 1438–1448 Melanie J. Bevill, Petinka I. Vlahova, and Jared P. Smit
Study of complex formation of carbamazepine with thiourea
Geetha Bolla, Sudhir Mittapalli, and Celecoxib cocrystal polymorphs Ashwini Nangi with cyclic amides: synthons of a sulfonamide drug with carboxamide coformers
Polymorphic cocrystals of nutraceutical compound p-coumaric acid with nicotinamide: characterization, relative solid-state stability, and conversion to alternate stoichiometries
ARTICLE IN PRESS
Giovanna Bruni, Mariarosa Maietta, Preparation and characterization of Vittorio Berbenni, Marcella Bini, carprofen cocrystals Stefania Ferrari, Doretta Capsoni, Massimo Boiocchi, Chiara Milanese, and Amedeo Marini
2014 CGD
14: 5079–5089 Shing Fung Chow, Limin Shi, Wai Kinetic entrapment of a hidden Wing Ng, Kari Hoi Yan Leung, curcumin cocrystal with Karthik Nagapudi, Changquan phloroglucinol Calvin Sun, and Albert H. L. Chow
Dapsone
2014 CGD
14: 4562–4573 Linglei Jiang, Ying Huang, Qi Preparation and solid-state Zhang, Hongyan He, Yun Xu, and characterization of dapsone Xuefeng Mei drug–drug co-crystals
Diflunisal
2014 IJP
466: 68–75
Efavirenz
2013 CGD
13: 1558–1569 Ariane Carla Campos de Melo, Isadora Ferreira de Amorim, Marilia de Lima Cirqueira, and Felipe Terra Martins
Ethenzamide
2012 CEC
14: 8515–8524 Srinivasulu Aitipamula, Annie B.H. Pharmaceutical cocrystals of Wong, Pui Shan Chow, and ethenzamide: structural, solubility Reginald B.H. Tan and dissolution studies
Etravirine
2013 CGD
13: 3681–3690 Lalit Rajput, Palash Sanphui, and Gautam R. Desiraju
vora, Ricardo A.E. Anto´nio O.L. E Castro, Teresa M.R. Maria, M. Ramos Silvac, J.H. ter Horst, Joa˜o Canotilho, and M. Ermelinda S. Eusebio
A thermodynamic based approach on the investigation of a diflunisal pharmaceutical cocrystal with improved intrinsic dissolution rate Toward novel solid-state forms of the anti-HIV drug efavirenz: from low screening success to cocrystals engineering strategies and discovery of a new polymorph
New solid forms of the anti-HIV drug etravirine: salts, cocrystals, and solubility Continued
ARTICLE IN PRESS
Curcumin
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2014 CGD
14: 4475–4486 Kumari Sugandha, Santanu Kaity, Samrat Mukherjee, Jinu Isaac, and Animesh Ghosh
Solubility enhancement of ezetimibe by a cocrystal engineering technique
Ezetimibe
2014 CEC
16: 8984–8993 Manishkumar R. Shimpi, Scott L. New cocrystals of ezetimibe with Childs, Dan Bostr€ om, and Sitaram P. L-proline and imidazole Velaga
Febuxostat
2013 CGD
13: 3188–3196 D. Maddileti, S.K. Jayabun, and Ashwini Nangia
Felodipine
2014 CEC
16: 6603–6611 Artem O. Surov, Katarzyna A. Polymorphism of felodipine Solanko, Andrew D. Bond, Annette cocrystals with 4,40 -bipyridine Bauer-Brandl, and German L. Perlovich
Fisetin
2013 CEC
15: 7696–7708 Michal Sowa, Katarzyna Slepokura, Cocrystals of fisetin, luteolin and and Ewa Matczak-Jon genistein with pyridinecarboxamide coformers: crystal structures, analysis of intermolecular interactions, spectral and thermal characterization
Fisetin
2014 CEC
16: Michal Sowa, Katarzyna Slepokura, Improving solubility of fisetin by 10,592–10,601 and Ewa Matczak-Jon cocrystallization
Flufenamic acid
2014 CEC
16: 5793–5801 Srinivasulu Aitipamula, Annie B.H. Cocrystallization with flufenamic Wong, Pui Shan Chow, and acid: comparison of physicochemical Reginald B.H. Tan properties of two pharmaceutical cocrystals
Soluble cocrystals of the xanthine oxidase inhibitor febuxostat
ARTICLE IN PRESS
Ezetimibe
2012 AC
B68: 431–443 Maya Tutughamiarso, Guido Wagner, and Ernst Egert
Cocrystals of 5-fluorocytosine. I. Coformers with fixed hydrogenbonding sites
Fluorocytosine
2012 AC
B68: 444–452 Maya Tutughamiarso and Ernst Egert
Cocrystals of 5-fluorocytosine. I. Coformers with variable hydrogenbonding sites
Fluorocytosine
2014 CGD
14: 4383–4393 Cecı´lia C.P. da Silva, Rebeka de O. Controlled synthesis of new Pepino, Cristiane C. de Melo, Juan 5-fluorocytosine cocrystals based on C. Tenorio, and Javier Ellena the pKa rule
Fluoroquinolone
2014 CGD
14: 3078–3095 Juan M. Martı´nez-Alejo, Jorge G. Domı´nguez-Cha´vez, Jesu´s RiveraIslas, Dea Herrera-Ruiz, Herbert H€ opfl, Hugo Morales-Rojas, and Juan P. Senosiain
Fluorouracil
2013 CEC
15: 73–77
Fluorouracil
2014 CEC
16: 6450–6458 Song Li, Jia-Mei Chen, and Tong- Synthon polymorphs of 1:1 cocrystal Bu Lu of 5-fluorouracil and 4-hydroxybenzoic acid: their relative stability and solvent polarity dependence of grinding outcomes
Furosemide
2012 AC
C68: 488–491 Dmitrijs Stepanovs and Anatoly Mishnev
A twist in cocrystals of salts: changes in packing and chloride coordination lead to opposite trends in the biopharmaceutical performance of fluoroquinolone hydrochloride cocrystals
Amit Delori, Mark D Eddleston, and Cocrystals of 5-fluorouracil William Jones
Multicomponent pharmaceutical cocrystals: furosemide and pentoxifylline Continued
ARTICLE IN PRESS
Fluorocytosine
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2012 JPS
101: 664–680
N. Rajesh Goud, Swarupa Gangavaram, Kuthuru Suresh, Sharmistha Pal, Sulur G. Manjunatha, Sudhir Nambiar, and Ashwini Nangia
Novel furosemide cocrystals and selection of high solubility drug forms
Furosemide
2014 CGD
14: 783–791
Bethany I. Harriss, Liana Vella-Zarb, Furosemide cocrystals: structures, Claire Wilson, and Ivana hydrogen bonding, and implications Radosavljevic Evans for properties
Furosemide
2014 CEC
16: 9979–9982 Vijay K. Srirambhatla, Arno Kraft, Stephen Watt, and Anthony V. Powell
Furosemide
2014 IJP
471: 478–484
Gabapentin lactam
2012 CEC
14: 4801–4811 Chinmay Maheshwari, V^ania Andre, Sreenivas Reddy, Lilly Roy, Teresa Duarte, and Naı´r Rodrı´guezHornedo
A robust two-dimensional hydrogen-bonded network for the predictable assembly of ternary cocrystals of furosemide
Mafalda C. Sarraguc¸a, Paulo R.S. A PAT approach for the on-line Ribeiro, Adenilson O. Santos, Marta monitoring of pharmaceutical C.D. Silva, and Joa˜o A. Lopes cocrystals formation with near infrared spectroscopy Tailoring aqueous solubility of a highly soluble compound via cocrystallization: effect of coformer ionization, pHmax and solute–solvent interactions
ARTICLE IN PRESS
Furosemide
2012 CGD
12: 2744–2747 Ramanpreet Kaur and Tayur N. Guru Row
Polymorphic anhydrous cocrystals of gallic acid and acetamide from methanol: pointers toward a stable cocrystal form
Genistein
2013 CEC
15: 7696–7708 Michal Sowa, Katarzyna Slepokura, Cocrystals of fisetin, luteolin and and Ewa Matczak-Jon genistein with pyridinecarboxamide coformers: crystal structures, analysis of intermolecular interactions, spectral and thermal characterization
Genistein
2013 AC
C69: 1267–1272
Gentisic acid
2012 CGD
12: 5763–5772 Vladimir Stilinovic and Branko Kaitner
Salts and cocrystals of gentisic acid with pyridine derivatives: the effect of proton transfer on the crystal packing
Griseofulvin
2012 CGD
12: 5858–5863 Srinivasulu Aitipamula, Venu R. Vangala, Pui Shan Chow, and Reginald B.H. Tan
Cocrystal hydrate of an antifungal drug, griseofulvin, with promising physicochemical properties
Haloprogin
2014 CEC
16: 5897–5904 Michele Baldrighi, Davide Polymorphs and cocrystals of Bartesaghi, Gabriella Cavallo, haloprogin: an antifungal agent Michele R. Chierotti, Roberto Gobetto, Pierangelo Metrangolo, Tullio Pilati, Giuseppe Resnati, and Giancarlo Terraneo
Michal Sowa, Katarzyna Slepokura, A 1:2 cocrystal of genistein with and Ewa Matczak-Jon isonicotinamide: crystal structure and Hirshfeld surface analysis
Continued
ARTICLE IN PRESS
Gallic acid
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
Hydrochlorothiazide 2014 CEC
16: 6996–7003 Jian-Rong Wang, Chanjuan Ye, and Structural and physicochemical Xuefeng Mei aspects of hydrochlorothiazide cocrystals
Hydrochlorothiazide 2014 AC
B70: 81–90
Ibuprofen
2012 CEC
14: 2386–2388 Kay Huai-Ying Hsi, Keith Separation of impurities from Chadwick, Amanda Fried, Meghan solution by selective cocrystal Kenny, and Allan S. Myerson formation
Ibuprofen
2012 IJP
426: 15–20
Ibuprofen
2013 CGD
13: 1510–1517 Frederico L.F. Soares and Renato L. Green synthesis of Carneiro ibuprofen–nicotinamide cocrystals and in-line evaluation by Raman spectroscopy
Indomethacin
2012 CEC
14: 6665–6674 Hassan Refat H. Ali, Amjad Alhalaweh, N.F.C. Mendes, Paulo Ribeiro-Claro, and Sitaram P. Velaga
Palash Sanphui and Lalit Rajput
Monitoring ibuprofen–nicotinamide cocrystal formation during solvent free continuous cocrystallization (SFCC) using near infrared spectroscopy as a PAT tool
Solid-state vibrational spectroscopic investigation of cocrystals and salt of indomethacin
ARTICLE IN PRESS
A.L. Kelly, T. Gough, R.S. Dhumal, S.A. Halsey, and A. Paradkar
Tuning solubility and stability of hydrochlorothiazide cocrystals
2012 JPBA
66: 162–169
Gang-Chun Zhang, Hong-Liang Lin, and Shan-Yang Lin
Thermal analysis and FTIR spectral curve-fitting investigation of formation mechanism and stability of indomethacin-saccharin cocrystals via solid-state grinding process
Indomethacin
2013 CGD
13: 2067–2074 Min-Jeong Lee, Nan-Hee Chun, Understanding the formation of In-Chun Wang, J. Jay Liu, Myung- indomethacin–saccharin cocrystals Yung Jeong, and Guang J. Choi by anti-solvent crystallization
Indomethacin
2013 CEC
15: 4041–4044 Mridul Majumder, Graham Buckton, Clare F. RawlinsonMalone, Adrian C. Williams, Mark J. Spillman, Elna Pidcock, and Kenneth Shankland
Indomethacin
2014 CGD
14: 643–648
Amjad Alhalaweh, Hassan Refat H. Effects of polymer and surfactant on Ali, and Sitaram P. Velaga the dissolution and transformation profiles of cocrystals in aqueous media
Indomethacin
2014 JPS
103: 2386–2395
Hong-Liang Lin, Gang-Chun Zhang, Yu-Ting Huang, and Shan-Yang Lin
Application of hydrogen-bond propensity calculations to an indomethacin–nicotinamide (1:1) cocrystal
An investigation of indomethacin–nicotinamide cocrystal formation induced by thermal stress in the solid or liquid state Continued
ARTICLE IN PRESS
Indomethacin
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2012 CEC
14: 2465–2478 Andreas Lemmerer
Covalent assistance to supramolecular synthesis: modifying the drug functionality of the antituberculosis API Isoniazid in situ during cocrystallization with GRAS and API compounds
Isoniazid
2013 CGD
13: 1082–1090 Inese Sarcevica, Liana Orola, Mikelis Crystal and molecular structure and V. Veidis, Anton Podjava, and stability of Isoniazid cocrystals with Sergey Belyakov selected carboxylic acids
Isoniazid
2013 CEC
15: 5877–5887 Srinivasulu Aitipamula, Annie B.H. Novel solid forms of the antiWong, Pui Shan Chow, and tuberculosis drug, Isoniazid: ternary Reginald B.H. Tan and polymorphic cocrystals
Isoniazid
2014 CGD
14: 5991–6005 Battini Swapna, D. Maddileti, and Ashwini Nangia
Isoniazid
2014 CGD
14: 423–426
Itraconazole
2012 AAPSPST
13: 1396–1406 Courtney A. Ober and Ram B. Gupt
Cocrystals of the tuberculosis drug Isoniazid: polymorphism, isostructurality, and stability
Ramanpreet Kaur, S.S.R.R. Structural insights into proton Perumal, Aninda J. Bhattacharyya, conduction in gallic acid–Isoniazid S. Yashonath, and T.N. Guru Row cocrystals Formation of itraconazole–succinic acid cocrystals by gas antisolvent cocrystallization
ARTICLE IN PRESS
Isoniazid
2013 CGD
13: 4877–4884 Anna Shevchenko, Inna Miroshnyk, Diversity in itraconazole cocrystals Lars-Olof Pietil€a, Jorma Haarala, with aliphatic dicarboxylic acids of Jukka Salmia, Kai Sinervo, varying chain length Sabiruddin Mirza, Bert van Veen, Erkki Kolehmainen, and Jouko Yliruusi
Itraconazole
2013 CGD
13: 346–351
Ketoconazole
2013 CGD
13: 4295–4304 Flavia A. Martin, Mihaela M. Pop, Ketoconazole salt and cocrystals Gheorghe Borodi, Xenia Filip, and with enhanced aqueous solubility Irina Kacso
Ketoprofen
2012 CEC
Separation of impurities from 14: 2386–2388 Kay Huai-Ying Hsi, Keith Chadwick, Amanda Fried, Meghan solution by selective cocrystal Kenny, and Allan S. Myerson formation
Lamotrigine
2012 CGD
12: 1847–1858 Edislav Leksˇic, Gordana Pavlovic, and Ernest Mesˇtrovic
Cocrystals of lamotrigine based on coformers involving carbonyl group discovered by hot-stage microscopy and DSC screening
Lenalidomide
2014 CGD
14: 3069–3077 Jia-Xi Song, Yan Yan, Jia Yao, Jia-Mei Chen, and Tong-Bu Lu
Improving the solubility of lenalidomide via cocrystals
Levetiracetam
2014 CGD
14: 2880–2892 Fanny George, Nikolay Tumanov, Does chirality influence the Bernadette Norberg, Koen tendency toward cocrystal Robeyns, Yaroslav Filinchuk, Johan formation? Wouters, and Tom Leyssens
Manu Lahtinen, Erkki Kolehmainen, Jorma Haarala, and Anna Shevchenko
Evidence of weak halogen bonding: new insights on itraconazole and its succinic acid cocrystal
Continued
ARTICLE IN PRESS
Itraconazole
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2013 CEC
15: 7696–7708 Michal Sowa, Katarzyna Slepokura, Cocrystals of fisetin, luteolin and and Ewa Matczak-Jon genistein with pyridinecarboxamide coformers: crystal structures, analysis of intermolecular interactions, spectral and thermal characterization
Mebendazole
2012 CEC
14: 6221–6229 Jia-Mei Chen, Zi-Zhou Wang, Chuan-Bin Wu, Song Li, and Tong-Bu Lu
Crystal engineering approach to improve the solubility of mebendazole
Melamine
2013 CEC
15: 5838–5843 Timothy J. Prior, Jennifer A. Armstrong, David M. Benoit, and Kayleigh L. Marshall
The structure of the melamine–cyanuric acid cocrystal
Meloxicam
2012 CEC
14: 305–313
Are meloxicam dimers really the structure-forming units in the ‘meloxicam–carboxylic acid’ cocrystals family? Relation between crystal structures and dissolution behaviour
Mercaptopurine
2012 CGD
12: 6004–6011 Lin-Lin Xu, Jia-Mei Chen, Yan Yan, and Tong-Bu Lu
Myricetin
2014 JMS
1058: 114–121 Michal Sowa, Katarzyna Slepokura, A 1:1 pharmaceutical cocrystal of and Ewa Matczak-Jon myricetin in combination with uncommon piracetam conformer: X-ray single crystal analysis and mechanochemical synthesis
Nikolay A. Tumanov, Svetlana A. Myz, Tatyana P. Shakhtshneider, and Elena V. Boldyreva
Improving the solubility of 6-mercaptopurine via cocrystals and salts
ARTICLE IN PRESS
Luteolin
2012 CGD
12: 4963–4971 Swarupa Gangavaram, S. Raghavender, Palash Sanphui, Sharmistha Pal, Sulur G. Manjunatha, Sudhir Nambiar, and Ashwini Nangia
Polymorphs and cocrystals of nalidixic acid
Nalidixic acid
2014 CGD
14: 1749–1755 Tudor Grecu, Harry Adams, Christopher A. Hunter, James F. McCabe, Anna Portell, and Rafel Prohens
Virtual screening identifies new cocrystals of nalidixic acid
Naproxen
2013 CEC
15: 3341–3350 Anae¨lle Tilborg, Geraldine Springuel, Bernadette Norberg, Johan Wouters, and Tom Leyssens
On the influence of using a zwitterionic coformer for cocrystallization: structural focus on naproxen–proline cocrystals
Naproxen
2014 CEC
16: 8185–8196 Natalia Tumanova, Nikolay Structural insight into Tumanov, Koen Robeyns, Yaroslav cocrystallization with zwitterionic Filinchuk, Johan Wouters, and Tom co-formers: cocrystals of S-naproxen Leyssens
Naproxen
2014 CEC
16: 5811–5819 K. Manoj, Rui Tamura, Hiroki Takahashi, and Hirohito Tsue
Crystal engineering of homochiral molecular organization of naproxen in cocrystals and their thermal phase transformation studies
Nevirapine
2012 CEC
14: 2541–2551 Mino R. Caira, Susan A. Bourne, Halima Samsodien, Emile Engel, Wilna Liebenberg, Nicole Stieger, and Marique Aucamp
Cocrystals of the antiretroviral nevirapine: crystal structures, thermal analysis and dissolution behaviour Continued
ARTICLE IN PRESS
Nalidixic acid
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
Niclosamide
2012 CGD
12: 4588–4599 Palash Sanphui, Sudalai Kumar, and Pharmaceutical cocrystals of Ashwini Nangia niclosamide
Nitazoxanide
2014 CGD
14: 1086–1102 Brenda C. Felix-Sonda, Jesu´s Rivera-Islas, Dea Herrera-Ruiz, Hugo Morales-Rojas, and Herbert H€ opfl
Nitrofurantoin
2012 CGD
12: 5925–5938 Venu R. Vangala, Pui Shan Chow, Cocrystals and cocrystal hydrates of and Reginald B.H. Tan the antibiotic nitrofurantoin: structural studies and physicochemical properties
Nitrofurantoin
2012 CEC
14: 5078–5088 Amjad Alhalaweh, Sumod George, Srinivas Basavoju, Scott L. Childs, Syed A.A. Rizvi, and Sitaram P. Velaga
Pharmaceutical cocrystals of nitrofurantoin: screening, characterization and crystal structure analysis
Oxcarbazepine
2012 CGD
12: 4211–4224 Renu Chadha, Anupam Saini, Dharamvir S. Jain, and P. Venugopalan
Preparation and solid-state characterization of three novel multicomponent solid forms of oxcarbazepine: improvement in solubility through saccharin cocrystal
Oxiracetam
2012 CGD
12: 4562–4566 Zi-Zhou Wang, Jia-Mei Chen, and Enhancing the hygroscopic stability Tong-Bu Lu of S-oxiracetam via pharmaceutical cocrystals
Nitazoxanide cocrystals in combination with succinic, glutaric, and 2,5-dihydroxybenzoic acid
ARTICLE IN PRESS
2014 CEC
16: 7667–7672 Tingting Zhang, Yan Yang, Xiaojun Zhao, Jiangtao Jia, Hongmin Su, Hongming He, Jingkai Gu, and Guangshan Zhu
Dissolution and pharmacokinetic properties of two paliperidone cocrystals with 4-hydroxybenzoic and 4-aminobenzoic acid
Paracetamol
2012 CGD
12: 4870–4879 Vijay K. Srirambhatla, Arno Kraft, Stephen Watt, and Anthony V. Powell
Crystal design approaches for the synthesis of paracetamol cocrystals
Paracetamol
2012 CEC
14: 5005–5014 V^ania Andre, M. Fa´tima M. da Piedade, and M. Teresa Duarte
Revisiting paracetamol in a quest for new cocrystals
Paracetamol
2013 CEC
15: 3799–3807 H.C. Stephen Chan, John Kendrick, Towards ab initio screening of Marcus A. Neumann, and Frank J.J. cocrystal formation through lattice Leusen energy calculations and crystal structure prediction of nicotinamide, isonicotinamide, picolinamide and paracetamol multi-component crystals
Paracetamol
2014 IJP
473: 179–186
Phenazopyridine
2012 CGD
12: 3144–3152 Qian Tao, Jia-Mei Chen, Lei Ma, and Tong-Bu Lu
Yusuke Maeno, Toshiro Fukami, Masatoshi Kawahata, Kentaro Yamaguchi, Tatsuaki Tagami, Tetsuya Ozeki, Toyofumi Suzuki, and KazuoTomono
Novel pharmaceutical cocrystal consisting of paracetamol and trimethylglycine, a new promising cocrystal former Phenazopyridine cocrystal and salts that exhibit enhanced solubility and stability Continued
ARTICLE IN PRESS
Paliperidone
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2012 CEC
14: 2381–2385 Srinivasulu Aitipamula, Pui Shan Chow, and Reginald B.H. Tan
Cocrystals of caffeine and piracetam with 4-hydroxybenzoic acid: unravelling the hidden hydrates of 1:1 cocrystals
Piracetam
2014 JMS
1058: 114–121 Michal Sowa, Katarzyna Slepokura, A 1:1 pharmaceutical cocrystal of and Ewa Matczak-Jon myricetin in combination with uncommon piracetam conformer: X-ray single crystal analysis and mechanochemical synthesis
Piroxicam
2012 CEC
14: 7264–7274 Craig Wales, Lynne H. Thomas, and Tautomerisation and polymorphism Chick C. Wilson in molecular complexes of piroxicam with mono-substituted benzoic acids
Piroxicam
2014 CGD
14: 3864–3874 Sayantan Chattoraj, Limin Shi, Miles Origin of deteriorated crystal Chen, Amjad Alhalaweh, Sitaram plasticity and compaction properties Velaga, and Changquan Calvin Sun of a 1:1 cocrystal between piroxicam and caccharin
Piroxicam
2014 CEC
16: 5924–5932 Lynne H. Thomas, Anneke R. Klapwijk, Craig Wales, and Chick C. Wilson
Intermolecular hydrogen transfer and solubility tuning in multicomponent molecular crystals of the API piroxicam
ARTICLE IN PRESS
Piracetam
Praziquantel
2013 CGD
13: 169–185
Julio C. Espinosa-Lara, Diana Guzman-Villanueva, Jenniffer I. Arenas-Garcı´a, Dea Herrera-Ruiz, Jesu´s Rivera-Islas, Perla Roma´nBravo, Hugo Morales-Rojas, and Herbert H€ opfl
Cocrystals of active pharmaceutical ingredients—praziquantel in combination with oxalic, malonic, succinic, maleic, fumaric, glutaric, adipic, and pimelic acids
13: 2098–2106 Yang-Hui Luo and Bai-Wang Sun
Pharmaceutical cocrystals of pyrazinecarboxamide with various carboxylic acids: crystallography, Hirshfeld surfaces, and dissolution study
Pyrimethamine
2013 CEC
15: 2916–2928 Amit Delori, Peter T.A. Galek, Elna Knowledge-based hydrogen bond Pidcock, Mohit Patni, and William prediction and the synthesis of salts Jones and cocrystals of the anti-malarial drug pyrimethamine with various drug and GRAS molecules
Quinoline
2012 CEC
14: 1967–1971 Sa´ndor L. Bek€ o, Martin U. Schmidt, An experimental screen for and Andrew D. Bond quinoline/fumaric acid salts and cocrystals
Ribavirin
2014 CGD
14: 6399–6408 Jia-Mei Chen, Song Li, and Tong-Bu Lu
Salicylic acid
2014 CGD
14: 2893–2899 Kyeong-Sill Lee, Kwang-Joo Kim, In situ monitoring of and Joachim Ulrich cocrystallization of salicylic acid– 4,40 -dipyridyl in solution using Raman spectroscopy
Pharmaceutical cocrystals of ribavirin with reduced release rates
Continued
ARTICLE IN PRESS
Pyrazinecarboxamide 2013 CGD
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2014 CEC
16: 5887–5896 Fabrizia Grepioni, Johan Wouters, Dario Braga, Saverio Nanna, Baptiste Fours, Gerard Coquerel, Geraldine Longfils, Sandrine Rome, Luc Aertse, and Luc Quere
Sildenafil
2014 CEC
16: 32–35
Stanozolol
2014 CGD
14: 3408–3422 Anae¨lle Tilborg, Geraldine Springuel, Bernadette Norberg, Johan Wouters, and Tom Leyssens
Sulfacetamide
2014 CEC
16: 5859–5869 N. Rajesh Goud, Ronaq Ali Khan, Modulating the solubility of and Ashwini Nangia sulfacetamide by means of cocrystals
Sulfathiazole
2014 CGD
14: 803–813
Tadalafil
2012 CEC
14: 2377–2380 David R. Weyna, Miranda L. Cheney, Ning Shan, Mazen Hanna, Lukasz Wojtas, and Michael J. Zaworotko
ˇ egarac, Edislav Leksˇic, Miroslav Z Primozˇ Sˇket, Janez Plavec, Maja Devcic Bogdanovic, DejanKresˇimir Bucar, Miljenko Dumic, and Ernest Mesˇtrovic
Ionic cocrystals of racetams: solidstate properties enhancement of neutral active pharmaceutical ingredients via addition of Mg2+ and Ca2+ chlorides A sildenafil cocrystal based on acetylsalicylic acid exhibits an enhanced intrinsic dissolution rate
How cocrystallization affects solidstate tautomerism: stanozolol case study
Yun Hu, Katarzyna Gniado, Andrea Mechanochemical reaction of Erxleben, and Patrick McArdle sulfathiazole with carboxylic acids: formation of a cocrystal, a salt, and coamorphous solids Crystal engineering of multiplecomponent organic solids: pharmaceutical cocrystals of tadalafil with persistent hydrogen bonding motifs
ARTICLE IN PRESS
Seletracetam
2014 CGD
14: 6557–6569 Srinivasulu Aitipamula, Pui Shan Chow, and Reginald B.H. Tan
Crystal engineering of tegafur cocrystals: structural analysis and physicochemical properties
Telmisartan
2014 CEC
16: 8375–8389 Renu Chadha, Swati Bhandari, Jamshed Haneef, Sadhika Khullar, and Sanjay Mandal
Cocrystals of telmisartan: characterization, structure elucidation, in vivo and toxicity studies
Temozolomide
2013 CGD
13: 2208–2219 Palash Sanphui, N. Jagadeesh Babu, Temozolomide cocrystals with and Ashwini Nangia carboxamide coformers
Tenoxicam
2013 CGD
Theophylline
2012 CEC
13: 1988–2003 Geetha Bolla, Palash Sanphui, and Solubility advantage of tenoxicam Ashwini Nangia phenolic cocrystals compared to salts ˚ ke C. Rasmuson The theophylline–oxalic acid 14: 4644–4655 Shuo Zhang and A cocrystal system: solid phases, thermodynamics and crystallisation
Theophylline
2012 CEC
14: 5128–5129 Sebastian Heiden, Lisa Tr€ obs, Klaus-J€ urgen Wenzel, and Franziska Emmerling
Mechanochemical synthesis and structural characterisation of a theophylline-benzoic acid cocrystal (1:1)
Theophylline
2012 CEC
14: 6163–6169 Heba Abourahma, Jennifer M. Urban, Nicole Morozowich, and Benny Chan
Examining the robustness of a theophylline cocrystal during grinding with additives Continued
ARTICLE IN PRESS
Tegafur
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2013 CGD
˚ ke C. Rasmuson Thermodynamics and crystallization 13: 1153–1161 Shuo Zhang and A of the theophylline–glutaric acid cocrystal
Theophylline
2013 AAPSPST
14: 265–276
Theophylline
2014 CGD
14: 5318–5328 Dejan-Kresˇimir Bucar, Rodger F. Henry, Geoff G.Z. Zhang, and Leonard R. MacGillivray
Synthon hierarchies in crystal forms composed of theophylline and hydroxybenzoic acids: cocrystal screening via solution-mediated phase transformation
Theophylline
2014 CEC
16: 3141–3147 Ping Li, Yueying Chu, Lin Wang, Robert M. Wenslow, Jr., Kaichao Yu, Hailu Zhang, and Zongwu Deng
Structure determination of the theophylline–nicotinamide cocrystal: a combined powder XRD, 1D solid-state NMR, and theoretical calculation study
Theophylline
2014 JPS
103: 2859–2864
An investigation of the causes of cocrystal dissociation at high humidity
Amjad Alhalaweh, Waseem Kaialy, Theophylline cocrystals prepared by Graham Buckton, and Hardyal Gill spray drying: physicochemical properties and aerosolization performance
Mark D. Eddleston, Ranjit Thakuria, Barry J. Aldous, and William Jones
ARTICLE IN PRESS
Theophylline
2014 JPBA
100: 322–328
Edyta Pindelska, Agnieszka Sokal, Solid-state NMR studies of Lukasz Szeleszczuk, Dariusz Maciej theophylline cocrystals with Pisklak, and Waclaw Kolodziejski dicarboxylic acids
Tolfenamic acid
2014 CEC
16: 8252–8262 K. Gaglioti, M.R. Chierotti, F. Improvement of the water solubility Grifasi, R. Gobetto, U.J. of tolfenamic acid by new multipleGriesser, D. Hasa, and D. Voinovich component crystals produced by mechanochemical methods
Tranilast
2013 CGD
13: 3546–3553 Na Geng, Jia-Mei Chen, Zi-Jian Li, Approach of cocrystallization to Long Jiang, and Tong-Bu Lu improve the solubility and photostability of tranilast
Trithiocyanuric acid 2014 CGD
14: 4803–4810 V. Nagarajan and Venkateswara Rao Preparation of multiple cocrystals of Pedireddi trithiocyanuric acid with some N-donor compounds
Trospium chloride
2014 CGD
14: 2931–2936 Veronika Sla´dkova´, Jana Cibulkova´, Application and comparison of Va´clav Eigner, Antonı´n Sˇturc, cocrystallization techniques on Bohumil Kratochvı´l, and Jan trospium chloride cocrystals Rohlı´cek
Voriconazole
2014 CEC
16: 4722–4731 S. Sudalai Kumar, Ranjit Thakuria, Pharmaceutical cocrystals and a and Ashwini Nangia nitrate salt of voriconazole
Vorinostat
2012 CEC
14: 362–365
Cristina Puigjaner, Rafael Barbas, A cocrystal is the key intermediates Anna Portell, Ismael Valverde, for the production of a new Xavier Vila, Xavier Alcobe, Merce` polymorph of Vorinostat Font-Bardia, and Rafel Prohens Continued
ARTICLE IN PRESS
Theophylline
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d
Journal abbreviations AAPS PharmSciTech
AC
Acta Crystallographica
CEC
CrystEngComm
CGD
Crystal Growth & Design
CPB
Chemical Pharmaceutical Bulletin
CS
Chemical Science
EJPS
European Journal of Pharmaceutical Sciences
IJP
International Journal of Pharmaceutics
JMS
Journal of Molecular Structure
JPBA
Journal of Pharmaceutical and Biomedical Analysis
JPS
Journal of Pharmaceutical Sciences
ARTICLE IN PRESS
AAPS-PST
ARTICLE IN PRESS Cocrystal Systems of Pharmaceutical Interest: 2012–2014
29
of publication. For each entry, the table also contains the bibliographic citation to the paper, a complete list of the authors, and the title of the paper. Although every attempt has been to do so, the coverage described herein cannot be represented as being encyclopedic or comprehensive. Apologies are rendered in advance to any scientist in the field whose works have been inadvertently omitted.
References [1] H.G. Brittain, Pharmaceutical cocrystals: the coming wave of new drug substances, J. Pharm. Sci. 102 (2013) 311–317. [2] O. Almarsson, M.L. Peterson, M. Zaworotko, The A to Z of pharmaceutical cocrystals: a decade of fast-moving new science and patents, Pharm. Pat. Anal. 1 (3) (2012) 313–327. [3] N. Blagden, S.J. Coles, D.J. Berry, Pharmaceutical cocrystals—are we there yet? CrstEngComm 16 (2014) 5753–5761. [4] C.B. Aaker€ oy, S. Forbes, J. Desper, Altering physical properties of pharmaceutical cocrystals in a systematic manner, CrstEngComm 16 (2014) 5870–5877. [5] D.P. Elder, R. Holm, H. Lopez de Diego, Use of pharmaceutical salts and cocrystals to address the issue of poor solubility, Int. J. Pharm. 453 (2013) 88–100. [6] R. Thakuria, A. Deloria, W. Jones, M.P. Lipert, L. Roy, N. Rodrı´guez-Hornedo, Pharmaceutical cocrystals and poorly soluble drugs, Int. J. Pharm. 453 (2013) 101–125. [7] H.G. Brittain, Cocrystal systems of pharmaceutical interest: 2007–2008, in: H.G. Brittain (Ed.), Chapter 9: Profiles of Drug Substances, Excipients, and Related Methodology, vol. 35, Elsevier Academic Press, Amsterdam, 2010, pp. 373–390. [8] H.G. Brittain, Cocrystal systems of pharmaceutical interest: 2009, in: H.G. Brittain (Ed.), Chapter 10: Profiles of Drug Substances, Excipients, and Related Methodology, vol. 35, Elsevier Academic Press, Amsterdam, 2011, pp. 361–381. [9] H.G. Brittain, Cocrystal systems of pharmaceutical interest: 2010, Cryst. Growth Des. 12 (2012) 1046–1054. [10] H.G. Brittain, Cocrystal systems of pharmaceutical interest: 2011, Cryst. Growth Des. 12 (2012) 5823–5832.
Cocrystal Systems of Pharmaceutical Interest: 2012–2014 Harry G. Brittain Center for Pharmaceutical Physics, Milford, NJ, United States
Contents References
29
Pharmaceutical scientists continue to recognize that one can oftentimes obtain a significant improvement in drug substance properties by simultaneously crystallizing the active ingredient with another substance in a single crystal lattice [1,2]. At present, the field still tends to be dominated by studies of mainly crystallographic interest, although a significant number of these entail work performed on compounds having pharmaceutical interest [3]. Nevertheless, research scientists have begun to take advantage of this structural information in the development of new routes of drug delivery [4]. Given the relatively poor solubility associated with many recently discovered compounds of pharmaceutical interest, it is not surprising that cocrystal systems are receiving ever increasing degrees of attention [5,6]. Developments in the field of pharmaceutical cocrystals have been documented in the form of chronological review articles [7–10]. The continuing rapid growth in the field, and the burgeoning number of compounds that have been cocrystallized, calls for compilations of the studies involved so that future work can continue along new pathways without duplication of the prior art. Accordingly, appropriate publications drawn from the major physical, crystallographic, and pharmaceutical journals are chronicled in the current review of the 2012–2014 literature, being sorted according to the identity of the drug substance involved. This information is contained in Table 1, where the primary sorting has been by compound name and year
Profiles of Drug Substances, Excipients, and Related Methodology ISSN 1871-5125 https://doi.org/10.1016/bs.podrm.2018.11.004
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2019 Elsevier Inc. All rights reserved.
1
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest Compound Year Journal Volume: pages Authors Title
2013 CEC
15: 4816–4822 John R.G. Sander, Dejan-Kresˇimir ‘Masked synthons’ in crystal Bucar, Rodger F. Henry, Brittany engineering: insulated components N. Giangiorgi, Geoff G.Z. Zhang, in acetaminophen cocrystal hydrates and Leonard R. MacGillivray
Acetazolamide
2012 CGD
12: 811–824
Jenniffer I. Arenas-Garcı´a, Dea Herrera-Ruiz, Karina Mondrago´nVa´squez, Hugo Morales-Rojas, and Herbert H€ opfl
Modification of the supramolecular hydrogen-bonding patterns of acetazolamide in the presence of different cocrystal formers: 3:1, 2:1, 1:1, and 1:2 cocrystals from screening with the structural isomers of hydroxybenzoic acids, aminobenzoic acids, hydroxybenzamides, aminobenzamides, nicotinic acids, nicotinamides, and 2,3dihydroxybenzoic acids
Acyclovir
2012 IJP
422: 160–169
Takaaki Masuda, Yasuo Yoshihashi, Etsuo Yonemochi, Kotaro Fujii, Hidehiro Uekusa, and Katsuhide Terada
Cocrystallization and amorphization induced by drug–excipient interaction improves the physical properties of acyclovir
Acyclovir
2013 CEC
15: 6457–6460 Yan Yan, Jia-Mei Chen, and Tong-Bu Lu
Simultaneously enhancing the solubility and permeability of acyclovir by crystal engineering approach
ARTICLE IN PRESS
Acetaminophen
2013 JPS
102: 4079–4086
Giovanna Bruni, Mariarosa Maietta, Lauretta Maggi, Piercarlo Mustarelli, Chiara Ferrara, Vittorio Berbenni, Chiara Milanese, Alessandro Girella, and AmedeoMarini
Adenine
2013 CGD
13: 1464–1472 Laura J. Thompson, Norhanida Elias, Louise Male, and Maryjane Tremayne
Agomelatine
2012 CGD
12: 2226–2233 Yan Yan, Jia-Mei Chen, Na Geng, Improving the solubility of and Tong-Bu Lu agomelatine via cocrystals
Aminosalicylic acid
2013 CGD
13: 360–366
Azelnidipine
2013 CEC
15: 3885–3891 Weiguang Lian, Yulong Lin, Min Crystal engineering approach to Wang, Caiqin Yang, and Jing Wang produce complex of azelnidipine with maleic acid
Baicalein
2012 AC
C68: 262–265 Michal Sowa, Katarzyna Slepokura, A 1:1 cocrystal of baicalein with and Ewa Matczak-Jon nicotinamide
Baicalein
2014 JPS
103: 2330–2337
Pramod Kumar Goswami, Ram Thaimattam, and Arunachalam Ramanan
Yanting Huang, Bowen Zhang, Yuan Gao, Jianjun Zhang, and Limin Shi
Preparation and physicochemical characterization of acyclovir cocrystals with improved dissolution properties Supramolecular behavior of adenine with succinic, fumaric, and maleic acids: tautomerism, cocrystallization, salt formation, and solvation
Multiple crystal forms of p-aminosalicylic acid: salts, salt cocrystal hydrate, cocrystals, and cocrystal polymorphs
Baicalein–nicotinamide cocrystal with enhanced solubility, dissolution, and oral bioavailability Continued
ARTICLE IN PRESS
Acyclovir
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2014 CEC
16: 5765–5768 M. Gryl, T. Seidler, K. Stadnicka, I. The crystal structure and optical Matulkova´, I. Nemec, N. properties of a pharmaceutical Tesarova´c, and P. Nemec cocrystal—the case of the melamine–barbital addition compound
Barbituric acid
2013 CEC
15: 7598–7605 Michele R. Chierotti, Katia Gaglioti, Roberto Gobetto, Dario Braga, Fabrizia Grepioni, and Lucia Maini
From molecular crystals to salt cocrystals of barbituric acid via the carbonate ion and an improvement of the solid state properties
Brivaracetam
2014 CEC
16: 5887–5896 Fabrizia Grepioni, Johan Wouters, Dario Braga, Saverio Nanna, Baptiste Fours, Gerard Coquerel, Geraldine Longfils, Sandrine Rome, Luc Aertse, and Luc Quere
Ionic cocrystals of racetams: solidstate properties enhancement of neutral active pharmaceutical ingredients via addition of Mg2+ and Ca2+ chlorides
Caffeine
2012 CGD
12: 1520–1530 Tom Leyssens, Geraldine Springuel, Importance of solvent selection for Riccardo Montis, Nadine Candoni, stoichiometrically diverse cocrystal and Stephane Veesler systems: caffeine/maleic acid 1:1 and 2:1 cocrystals
Caffeine
2012 CEC
14: 2444–2453 Soumyajit Ghosha and C. Malla Reddy
Cocrystals of caffeine with substituted nitroanilines and nitrobenzoic acids: structure–mechanical property and thermal studies
ARTICLE IN PRESS
Barbital
2012 CEC
14: 2381–2385 Srinivasulu Aitipamula, Pui Shan Chow, and Reginald B.H. Tan
Cocrystals of caffeine and piracetam with 4-hydroxybenzoic acid: unravelling the hidden hydrates of 1:1 cocrystals
Caffeine
2013 CGD
13: 4435–4441 Soumyajit Ghosh, Arobendo Mondal, M.S.R.N. Kiran, U. Ramamurty, and C. Malla Reddy
The role of weak interactions in the phase transition and distinct mechanical behavior of two structurally similar caffeine cocrystal polymorphs studied by nanoindentation
Caffeine
2013 CEC
15: 3705–3710 Sudhir Pagire, Sachin Korde, Rohan Ambardekar, Shivprasad Deshmukh, Radha Charan Dash, Ravindra Dhumal, and Anant Paradkar
Microwave assisted synthesis of caffeine/maleic acid cocrystals: the role of the dielectric and physicochemical properties of the solvent
Caffeine
2013 Chemical 4: 4417–4425 Science
Caffeine
2014 CGD
Dejan-Kresˇimir Bucar, Graeme M. Day, Ivan Halasz, Geoff G.Z. Zhang, John R.G. Sander, David G. Reid, Leonard R. MacGillivray, Melinda J. Duer, and William Jones
The curious case of (caffeine) (benzoic acid): how heteronuclear seeding allowed the formation of an elusive cocrystal
14: 3949–3957 Zai Qun Yu, Pui Shan Chow, and Design space for polymorphic Reginald B.H. Tan co-crystallization: incorporating process model uncertainty and operational variability Continued
ARTICLE IN PRESS
Caffeine
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2014 CEC
16: 8272–8278 Franziska Fischer, Gudrun Scholz, Sigrid Benemann, Klaus Rademannb, and Franziska Emmerling
Evaluation of the formation pathways of cocrystal polymorphs in liquid-assisted syntheses
Caffeine
2014 CEC
16: 9603–9611 T. Leyssens, N. Tumanova, K. Robeyns, N. Candonib, and S. Veesler
Solution cocrystallization, an effective tool to explore the variety of cocrystal systems: caffeine/ dicarboxylic acid cocrystals
Caffeine
2014 AC
B70: 72–80
Nadeesh Madusanka, Mark D. Polymorphs, hydrates and solvates of Eddleston, Mihails Arhangelskis, and a cocrystal of caffeine with William Jones anthranilic acid
Caffeine
2014 JPS
103: 2859–2864
Mark D. Eddleston, Ranjit Thakuria, Barry J. Aldous, and William Jones
An investigation of the causes of cocrystal dissociation at high humidity
Caffeine
2014 JPS
103: 2865–2870
Mark D. Eddleston, Nadeesh Madusanka, and William Jones
Cocrystal dissociation in the presence of water: a general approach for identifying stable cocrystal forms
Carbamazepine
2013 CGD
13: 4162–4167 Sudhir K. Pagire, Sachin A. Korde, Spherical crystallization of Benjamin R. Whiteside, John carbamazepine/saccharin cocrystals: Kendrick, and Anant Paradkar selective agglomeration and purification through surface interactions
ARTICLE IN PRESS
Caffeine
Carbamazepine
2013 CEC
15: 3862–3873 Syarifah Abd Rahim, Robert B. A comparative assessment of the Hammond, Ahmad Y. Sheikh, and influence of different crystallization Kevin J. Roberts screening methodologies on the solid forms of carbamazepine cocrystals
Carbamazepine
2013 IJP
450: 311–322
Carbamazepine
2014 CGD
14: 6508–6513 Amanda R. Buist and Alan R. Kennedy
Carbamazepine
2014 CGD
14: 189–198
Carbamazepine
2014 CEC
16: 3573–3583 Hiren G. Moradiya, Muhammad T. Continuous cocrystallisation of Islam, Sheelagh Halsey, Mohammed carbamazepine and trans-cinnamic Maniruzzaman, Babur Z. acid via melt extrusion processing Chowdhry, Martin J. Snowdena, and D. Douroumis
Carbamazepine
2014 JPS
*****103: 2904–2910
Anti-solvent cocrystallization of carbamazepine and saccharin Ionic cocrystals of pharmaceutical compounds: sodium complexes of carbamazepine
Hiren Moradiya, Muhammad T. Continuous cocrystallization for Islam, Grahame R. Woollam, Ian J. dissolution rate optimization of a Slipper, Sheelagh Halsey, Martin J. poorly water-soluble drug Snowden, and D. Douroumis
Kevin Boksa, Andrew Otte, and Rodolfo Pinal
Matrix-assisted cocrystallization (MAC) simultaneous production and formulation of pharmaceutical cocrystals by hot-melt extrusion Continued
ARTICLE IN PRESS
In-Chun Wang, Min-Jeong Lee, Sang-Jun Sim, Woo-Sik Kim, and Guang J. Choi
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
Carbamazepine
2014 EJPS
62: 251–257
Shashank P. Patil, Sameer R. Modi, Generation of 1:1 carbamazepine: and Arvind K. Bansal nicotinamide cocrystals by spray drying
Carbamazepine
2014 CPB
62: 1125–1130 Yutaka Inoue, Sayuri Sato, Chisa Yamamoto, Mikio Yamasaki, and Ikuo Kanamo
Carprofen
2012 CEC
Celecoxib
2014 CEC
16: 24–27
Celecoxib
2014 CEC
16: Xiaojuan Wang, Qi Zhang, Linglei Isostructurality in six celecoxib 10,959–10,968 Jiang, Yun Xu, and Xuefeng Mei cocrystals introduced by solvent inclusion
Coumaric acid
2014 CGD
14: 1438–1448 Melanie J. Bevill, Petinka I. Vlahova, and Jared P. Smit
Study of complex formation of carbamazepine with thiourea
Geetha Bolla, Sudhir Mittapalli, and Celecoxib cocrystal polymorphs Ashwini Nangi with cyclic amides: synthons of a sulfonamide drug with carboxamide coformers
Polymorphic cocrystals of nutraceutical compound p-coumaric acid with nicotinamide: characterization, relative solid-state stability, and conversion to alternate stoichiometries
ARTICLE IN PRESS
Giovanna Bruni, Mariarosa Maietta, Preparation and characterization of Vittorio Berbenni, Marcella Bini, carprofen cocrystals Stefania Ferrari, Doretta Capsoni, Massimo Boiocchi, Chiara Milanese, and Amedeo Marini
2014 CGD
14: 5079–5089 Shing Fung Chow, Limin Shi, Wai Kinetic entrapment of a hidden Wing Ng, Kari Hoi Yan Leung, curcumin cocrystal with Karthik Nagapudi, Changquan phloroglucinol Calvin Sun, and Albert H. L. Chow
Dapsone
2014 CGD
14: 4562–4573 Linglei Jiang, Ying Huang, Qi Preparation and solid-state Zhang, Hongyan He, Yun Xu, and characterization of dapsone Xuefeng Mei drug–drug co-crystals
Diflunisal
2014 IJP
466: 68–75
Efavirenz
2013 CGD
13: 1558–1569 Ariane Carla Campos de Melo, Isadora Ferreira de Amorim, Marilia de Lima Cirqueira, and Felipe Terra Martins
Ethenzamide
2012 CEC
14: 8515–8524 Srinivasulu Aitipamula, Annie B.H. Pharmaceutical cocrystals of Wong, Pui Shan Chow, and ethenzamide: structural, solubility Reginald B.H. Tan and dissolution studies
Etravirine
2013 CGD
13: 3681–3690 Lalit Rajput, Palash Sanphui, and Gautam R. Desiraju
vora, Ricardo A.E. Anto´nio O.L. E Castro, Teresa M.R. Maria, M. Ramos Silvac, J.H. ter Horst, Joa˜o Canotilho, and M. Ermelinda S. Eusebio
A thermodynamic based approach on the investigation of a diflunisal pharmaceutical cocrystal with improved intrinsic dissolution rate Toward novel solid-state forms of the anti-HIV drug efavirenz: from low screening success to cocrystals engineering strategies and discovery of a new polymorph
New solid forms of the anti-HIV drug etravirine: salts, cocrystals, and solubility Continued
ARTICLE IN PRESS
Curcumin
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2014 CGD
14: 4475–4486 Kumari Sugandha, Santanu Kaity, Samrat Mukherjee, Jinu Isaac, and Animesh Ghosh
Solubility enhancement of ezetimibe by a cocrystal engineering technique
Ezetimibe
2014 CEC
16: 8984–8993 Manishkumar R. Shimpi, Scott L. New cocrystals of ezetimibe with Childs, Dan Bostr€ om, and Sitaram P. L-proline and imidazole Velaga
Febuxostat
2013 CGD
13: 3188–3196 D. Maddileti, S.K. Jayabun, and Ashwini Nangia
Felodipine
2014 CEC
16: 6603–6611 Artem O. Surov, Katarzyna A. Polymorphism of felodipine Solanko, Andrew D. Bond, Annette cocrystals with 4,40 -bipyridine Bauer-Brandl, and German L. Perlovich
Fisetin
2013 CEC
15: 7696–7708 Michal Sowa, Katarzyna Slepokura, Cocrystals of fisetin, luteolin and and Ewa Matczak-Jon genistein with pyridinecarboxamide coformers: crystal structures, analysis of intermolecular interactions, spectral and thermal characterization
Fisetin
2014 CEC
16: Michal Sowa, Katarzyna Slepokura, Improving solubility of fisetin by 10,592–10,601 and Ewa Matczak-Jon cocrystallization
Flufenamic acid
2014 CEC
16: 5793–5801 Srinivasulu Aitipamula, Annie B.H. Cocrystallization with flufenamic Wong, Pui Shan Chow, and acid: comparison of physicochemical Reginald B.H. Tan properties of two pharmaceutical cocrystals
Soluble cocrystals of the xanthine oxidase inhibitor febuxostat
ARTICLE IN PRESS
Ezetimibe
2012 AC
B68: 431–443 Maya Tutughamiarso, Guido Wagner, and Ernst Egert
Cocrystals of 5-fluorocytosine. I. Coformers with fixed hydrogenbonding sites
Fluorocytosine
2012 AC
B68: 444–452 Maya Tutughamiarso and Ernst Egert
Cocrystals of 5-fluorocytosine. I. Coformers with variable hydrogenbonding sites
Fluorocytosine
2014 CGD
14: 4383–4393 Cecı´lia C.P. da Silva, Rebeka de O. Controlled synthesis of new Pepino, Cristiane C. de Melo, Juan 5-fluorocytosine cocrystals based on C. Tenorio, and Javier Ellena the pKa rule
Fluoroquinolone
2014 CGD
14: 3078–3095 Juan M. Martı´nez-Alejo, Jorge G. Domı´nguez-Cha´vez, Jesu´s RiveraIslas, Dea Herrera-Ruiz, Herbert H€ opfl, Hugo Morales-Rojas, and Juan P. Senosiain
Fluorouracil
2013 CEC
15: 73–77
Fluorouracil
2014 CEC
16: 6450–6458 Song Li, Jia-Mei Chen, and Tong- Synthon polymorphs of 1:1 cocrystal Bu Lu of 5-fluorouracil and 4-hydroxybenzoic acid: their relative stability and solvent polarity dependence of grinding outcomes
Furosemide
2012 AC
C68: 488–491 Dmitrijs Stepanovs and Anatoly Mishnev
A twist in cocrystals of salts: changes in packing and chloride coordination lead to opposite trends in the biopharmaceutical performance of fluoroquinolone hydrochloride cocrystals
Amit Delori, Mark D Eddleston, and Cocrystals of 5-fluorouracil William Jones
Multicomponent pharmaceutical cocrystals: furosemide and pentoxifylline Continued
ARTICLE IN PRESS
Fluorocytosine
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2012 JPS
101: 664–680
N. Rajesh Goud, Swarupa Gangavaram, Kuthuru Suresh, Sharmistha Pal, Sulur G. Manjunatha, Sudhir Nambiar, and Ashwini Nangia
Novel furosemide cocrystals and selection of high solubility drug forms
Furosemide
2014 CGD
14: 783–791
Bethany I. Harriss, Liana Vella-Zarb, Furosemide cocrystals: structures, Claire Wilson, and Ivana hydrogen bonding, and implications Radosavljevic Evans for properties
Furosemide
2014 CEC
16: 9979–9982 Vijay K. Srirambhatla, Arno Kraft, Stephen Watt, and Anthony V. Powell
Furosemide
2014 IJP
471: 478–484
Gabapentin lactam
2012 CEC
14: 4801–4811 Chinmay Maheshwari, V^ania Andre, Sreenivas Reddy, Lilly Roy, Teresa Duarte, and Naı´r Rodrı´guezHornedo
A robust two-dimensional hydrogen-bonded network for the predictable assembly of ternary cocrystals of furosemide
Mafalda C. Sarraguc¸a, Paulo R.S. A PAT approach for the on-line Ribeiro, Adenilson O. Santos, Marta monitoring of pharmaceutical C.D. Silva, and Joa˜o A. Lopes cocrystals formation with near infrared spectroscopy Tailoring aqueous solubility of a highly soluble compound via cocrystallization: effect of coformer ionization, pHmax and solute–solvent interactions
ARTICLE IN PRESS
Furosemide
2012 CGD
12: 2744–2747 Ramanpreet Kaur and Tayur N. Guru Row
Polymorphic anhydrous cocrystals of gallic acid and acetamide from methanol: pointers toward a stable cocrystal form
Genistein
2013 CEC
15: 7696–7708 Michal Sowa, Katarzyna Slepokura, Cocrystals of fisetin, luteolin and and Ewa Matczak-Jon genistein with pyridinecarboxamide coformers: crystal structures, analysis of intermolecular interactions, spectral and thermal characterization
Genistein
2013 AC
C69: 1267–1272
Gentisic acid
2012 CGD
12: 5763–5772 Vladimir Stilinovic and Branko Kaitner
Salts and cocrystals of gentisic acid with pyridine derivatives: the effect of proton transfer on the crystal packing
Griseofulvin
2012 CGD
12: 5858–5863 Srinivasulu Aitipamula, Venu R. Vangala, Pui Shan Chow, and Reginald B.H. Tan
Cocrystal hydrate of an antifungal drug, griseofulvin, with promising physicochemical properties
Haloprogin
2014 CEC
16: 5897–5904 Michele Baldrighi, Davide Polymorphs and cocrystals of Bartesaghi, Gabriella Cavallo, haloprogin: an antifungal agent Michele R. Chierotti, Roberto Gobetto, Pierangelo Metrangolo, Tullio Pilati, Giuseppe Resnati, and Giancarlo Terraneo
Michal Sowa, Katarzyna Slepokura, A 1:2 cocrystal of genistein with and Ewa Matczak-Jon isonicotinamide: crystal structure and Hirshfeld surface analysis
Continued
ARTICLE IN PRESS
Gallic acid
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
Hydrochlorothiazide 2014 CEC
16: 6996–7003 Jian-Rong Wang, Chanjuan Ye, and Structural and physicochemical Xuefeng Mei aspects of hydrochlorothiazide cocrystals
Hydrochlorothiazide 2014 AC
B70: 81–90
Ibuprofen
2012 CEC
14: 2386–2388 Kay Huai-Ying Hsi, Keith Separation of impurities from Chadwick, Amanda Fried, Meghan solution by selective cocrystal Kenny, and Allan S. Myerson formation
Ibuprofen
2012 IJP
426: 15–20
Ibuprofen
2013 CGD
13: 1510–1517 Frederico L.F. Soares and Renato L. Green synthesis of Carneiro ibuprofen–nicotinamide cocrystals and in-line evaluation by Raman spectroscopy
Indomethacin
2012 CEC
14: 6665–6674 Hassan Refat H. Ali, Amjad Alhalaweh, N.F.C. Mendes, Paulo Ribeiro-Claro, and Sitaram P. Velaga
Palash Sanphui and Lalit Rajput
Monitoring ibuprofen–nicotinamide cocrystal formation during solvent free continuous cocrystallization (SFCC) using near infrared spectroscopy as a PAT tool
Solid-state vibrational spectroscopic investigation of cocrystals and salt of indomethacin
ARTICLE IN PRESS
A.L. Kelly, T. Gough, R.S. Dhumal, S.A. Halsey, and A. Paradkar
Tuning solubility and stability of hydrochlorothiazide cocrystals
2012 JPBA
66: 162–169
Gang-Chun Zhang, Hong-Liang Lin, and Shan-Yang Lin
Thermal analysis and FTIR spectral curve-fitting investigation of formation mechanism and stability of indomethacin-saccharin cocrystals via solid-state grinding process
Indomethacin
2013 CGD
13: 2067–2074 Min-Jeong Lee, Nan-Hee Chun, Understanding the formation of In-Chun Wang, J. Jay Liu, Myung- indomethacin–saccharin cocrystals Yung Jeong, and Guang J. Choi by anti-solvent crystallization
Indomethacin
2013 CEC
15: 4041–4044 Mridul Majumder, Graham Buckton, Clare F. RawlinsonMalone, Adrian C. Williams, Mark J. Spillman, Elna Pidcock, and Kenneth Shankland
Indomethacin
2014 CGD
14: 643–648
Amjad Alhalaweh, Hassan Refat H. Effects of polymer and surfactant on Ali, and Sitaram P. Velaga the dissolution and transformation profiles of cocrystals in aqueous media
Indomethacin
2014 JPS
103: 2386–2395
Hong-Liang Lin, Gang-Chun Zhang, Yu-Ting Huang, and Shan-Yang Lin
Application of hydrogen-bond propensity calculations to an indomethacin–nicotinamide (1:1) cocrystal
An investigation of indomethacin–nicotinamide cocrystal formation induced by thermal stress in the solid or liquid state Continued
ARTICLE IN PRESS
Indomethacin
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2012 CEC
14: 2465–2478 Andreas Lemmerer
Covalent assistance to supramolecular synthesis: modifying the drug functionality of the antituberculosis API Isoniazid in situ during cocrystallization with GRAS and API compounds
Isoniazid
2013 CGD
13: 1082–1090 Inese Sarcevica, Liana Orola, Mikelis Crystal and molecular structure and V. Veidis, Anton Podjava, and stability of Isoniazid cocrystals with Sergey Belyakov selected carboxylic acids
Isoniazid
2013 CEC
15: 5877–5887 Srinivasulu Aitipamula, Annie B.H. Novel solid forms of the antiWong, Pui Shan Chow, and tuberculosis drug, Isoniazid: ternary Reginald B.H. Tan and polymorphic cocrystals
Isoniazid
2014 CGD
14: 5991–6005 Battini Swapna, D. Maddileti, and Ashwini Nangia
Isoniazid
2014 CGD
14: 423–426
Itraconazole
2012 AAPSPST
13: 1396–1406 Courtney A. Ober and Ram B. Gupt
Cocrystals of the tuberculosis drug Isoniazid: polymorphism, isostructurality, and stability
Ramanpreet Kaur, S.S.R.R. Structural insights into proton Perumal, Aninda J. Bhattacharyya, conduction in gallic acid–Isoniazid S. Yashonath, and T.N. Guru Row cocrystals Formation of itraconazole–succinic acid cocrystals by gas antisolvent cocrystallization
ARTICLE IN PRESS
Isoniazid
2013 CGD
13: 4877–4884 Anna Shevchenko, Inna Miroshnyk, Diversity in itraconazole cocrystals Lars-Olof Pietil€a, Jorma Haarala, with aliphatic dicarboxylic acids of Jukka Salmia, Kai Sinervo, varying chain length Sabiruddin Mirza, Bert van Veen, Erkki Kolehmainen, and Jouko Yliruusi
Itraconazole
2013 CGD
13: 346–351
Ketoconazole
2013 CGD
13: 4295–4304 Flavia A. Martin, Mihaela M. Pop, Ketoconazole salt and cocrystals Gheorghe Borodi, Xenia Filip, and with enhanced aqueous solubility Irina Kacso
Ketoprofen
2012 CEC
Separation of impurities from 14: 2386–2388 Kay Huai-Ying Hsi, Keith Chadwick, Amanda Fried, Meghan solution by selective cocrystal Kenny, and Allan S. Myerson formation
Lamotrigine
2012 CGD
12: 1847–1858 Edislav Leksˇic, Gordana Pavlovic, and Ernest Mesˇtrovic
Cocrystals of lamotrigine based on coformers involving carbonyl group discovered by hot-stage microscopy and DSC screening
Lenalidomide
2014 CGD
14: 3069–3077 Jia-Xi Song, Yan Yan, Jia Yao, Jia-Mei Chen, and Tong-Bu Lu
Improving the solubility of lenalidomide via cocrystals
Levetiracetam
2014 CGD
14: 2880–2892 Fanny George, Nikolay Tumanov, Does chirality influence the Bernadette Norberg, Koen tendency toward cocrystal Robeyns, Yaroslav Filinchuk, Johan formation? Wouters, and Tom Leyssens
Manu Lahtinen, Erkki Kolehmainen, Jorma Haarala, and Anna Shevchenko
Evidence of weak halogen bonding: new insights on itraconazole and its succinic acid cocrystal
Continued
ARTICLE IN PRESS
Itraconazole
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2013 CEC
15: 7696–7708 Michal Sowa, Katarzyna Slepokura, Cocrystals of fisetin, luteolin and and Ewa Matczak-Jon genistein with pyridinecarboxamide coformers: crystal structures, analysis of intermolecular interactions, spectral and thermal characterization
Mebendazole
2012 CEC
14: 6221–6229 Jia-Mei Chen, Zi-Zhou Wang, Chuan-Bin Wu, Song Li, and Tong-Bu Lu
Crystal engineering approach to improve the solubility of mebendazole
Melamine
2013 CEC
15: 5838–5843 Timothy J. Prior, Jennifer A. Armstrong, David M. Benoit, and Kayleigh L. Marshall
The structure of the melamine–cyanuric acid cocrystal
Meloxicam
2012 CEC
14: 305–313
Are meloxicam dimers really the structure-forming units in the ‘meloxicam–carboxylic acid’ cocrystals family? Relation between crystal structures and dissolution behaviour
Mercaptopurine
2012 CGD
12: 6004–6011 Lin-Lin Xu, Jia-Mei Chen, Yan Yan, and Tong-Bu Lu
Myricetin
2014 JMS
1058: 114–121 Michal Sowa, Katarzyna Slepokura, A 1:1 pharmaceutical cocrystal of and Ewa Matczak-Jon myricetin in combination with uncommon piracetam conformer: X-ray single crystal analysis and mechanochemical synthesis
Nikolay A. Tumanov, Svetlana A. Myz, Tatyana P. Shakhtshneider, and Elena V. Boldyreva
Improving the solubility of 6-mercaptopurine via cocrystals and salts
ARTICLE IN PRESS
Luteolin
2012 CGD
12: 4963–4971 Swarupa Gangavaram, S. Raghavender, Palash Sanphui, Sharmistha Pal, Sulur G. Manjunatha, Sudhir Nambiar, and Ashwini Nangia
Polymorphs and cocrystals of nalidixic acid
Nalidixic acid
2014 CGD
14: 1749–1755 Tudor Grecu, Harry Adams, Christopher A. Hunter, James F. McCabe, Anna Portell, and Rafel Prohens
Virtual screening identifies new cocrystals of nalidixic acid
Naproxen
2013 CEC
15: 3341–3350 Anae¨lle Tilborg, Geraldine Springuel, Bernadette Norberg, Johan Wouters, and Tom Leyssens
On the influence of using a zwitterionic coformer for cocrystallization: structural focus on naproxen–proline cocrystals
Naproxen
2014 CEC
16: 8185–8196 Natalia Tumanova, Nikolay Structural insight into Tumanov, Koen Robeyns, Yaroslav cocrystallization with zwitterionic Filinchuk, Johan Wouters, and Tom co-formers: cocrystals of S-naproxen Leyssens
Naproxen
2014 CEC
16: 5811–5819 K. Manoj, Rui Tamura, Hiroki Takahashi, and Hirohito Tsue
Crystal engineering of homochiral molecular organization of naproxen in cocrystals and their thermal phase transformation studies
Nevirapine
2012 CEC
14: 2541–2551 Mino R. Caira, Susan A. Bourne, Halima Samsodien, Emile Engel, Wilna Liebenberg, Nicole Stieger, and Marique Aucamp
Cocrystals of the antiretroviral nevirapine: crystal structures, thermal analysis and dissolution behaviour Continued
ARTICLE IN PRESS
Nalidixic acid
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
Niclosamide
2012 CGD
12: 4588–4599 Palash Sanphui, Sudalai Kumar, and Pharmaceutical cocrystals of Ashwini Nangia niclosamide
Nitazoxanide
2014 CGD
14: 1086–1102 Brenda C. Felix-Sonda, Jesu´s Rivera-Islas, Dea Herrera-Ruiz, Hugo Morales-Rojas, and Herbert H€ opfl
Nitrofurantoin
2012 CGD
12: 5925–5938 Venu R. Vangala, Pui Shan Chow, Cocrystals and cocrystal hydrates of and Reginald B.H. Tan the antibiotic nitrofurantoin: structural studies and physicochemical properties
Nitrofurantoin
2012 CEC
14: 5078–5088 Amjad Alhalaweh, Sumod George, Srinivas Basavoju, Scott L. Childs, Syed A.A. Rizvi, and Sitaram P. Velaga
Pharmaceutical cocrystals of nitrofurantoin: screening, characterization and crystal structure analysis
Oxcarbazepine
2012 CGD
12: 4211–4224 Renu Chadha, Anupam Saini, Dharamvir S. Jain, and P. Venugopalan
Preparation and solid-state characterization of three novel multicomponent solid forms of oxcarbazepine: improvement in solubility through saccharin cocrystal
Oxiracetam
2012 CGD
12: 4562–4566 Zi-Zhou Wang, Jia-Mei Chen, and Enhancing the hygroscopic stability Tong-Bu Lu of S-oxiracetam via pharmaceutical cocrystals
Nitazoxanide cocrystals in combination with succinic, glutaric, and 2,5-dihydroxybenzoic acid
ARTICLE IN PRESS
2014 CEC
16: 7667–7672 Tingting Zhang, Yan Yang, Xiaojun Zhao, Jiangtao Jia, Hongmin Su, Hongming He, Jingkai Gu, and Guangshan Zhu
Dissolution and pharmacokinetic properties of two paliperidone cocrystals with 4-hydroxybenzoic and 4-aminobenzoic acid
Paracetamol
2012 CGD
12: 4870–4879 Vijay K. Srirambhatla, Arno Kraft, Stephen Watt, and Anthony V. Powell
Crystal design approaches for the synthesis of paracetamol cocrystals
Paracetamol
2012 CEC
14: 5005–5014 V^ania Andre, M. Fa´tima M. da Piedade, and M. Teresa Duarte
Revisiting paracetamol in a quest for new cocrystals
Paracetamol
2013 CEC
15: 3799–3807 H.C. Stephen Chan, John Kendrick, Towards ab initio screening of Marcus A. Neumann, and Frank J.J. cocrystal formation through lattice Leusen energy calculations and crystal structure prediction of nicotinamide, isonicotinamide, picolinamide and paracetamol multi-component crystals
Paracetamol
2014 IJP
473: 179–186
Phenazopyridine
2012 CGD
12: 3144–3152 Qian Tao, Jia-Mei Chen, Lei Ma, and Tong-Bu Lu
Yusuke Maeno, Toshiro Fukami, Masatoshi Kawahata, Kentaro Yamaguchi, Tatsuaki Tagami, Tetsuya Ozeki, Toyofumi Suzuki, and KazuoTomono
Novel pharmaceutical cocrystal consisting of paracetamol and trimethylglycine, a new promising cocrystal former Phenazopyridine cocrystal and salts that exhibit enhanced solubility and stability Continued
ARTICLE IN PRESS
Paliperidone
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2012 CEC
14: 2381–2385 Srinivasulu Aitipamula, Pui Shan Chow, and Reginald B.H. Tan
Cocrystals of caffeine and piracetam with 4-hydroxybenzoic acid: unravelling the hidden hydrates of 1:1 cocrystals
Piracetam
2014 JMS
1058: 114–121 Michal Sowa, Katarzyna Slepokura, A 1:1 pharmaceutical cocrystal of and Ewa Matczak-Jon myricetin in combination with uncommon piracetam conformer: X-ray single crystal analysis and mechanochemical synthesis
Piroxicam
2012 CEC
14: 7264–7274 Craig Wales, Lynne H. Thomas, and Tautomerisation and polymorphism Chick C. Wilson in molecular complexes of piroxicam with mono-substituted benzoic acids
Piroxicam
2014 CGD
14: 3864–3874 Sayantan Chattoraj, Limin Shi, Miles Origin of deteriorated crystal Chen, Amjad Alhalaweh, Sitaram plasticity and compaction properties Velaga, and Changquan Calvin Sun of a 1:1 cocrystal between piroxicam and caccharin
Piroxicam
2014 CEC
16: 5924–5932 Lynne H. Thomas, Anneke R. Klapwijk, Craig Wales, and Chick C. Wilson
Intermolecular hydrogen transfer and solubility tuning in multicomponent molecular crystals of the API piroxicam
ARTICLE IN PRESS
Piracetam
Praziquantel
2013 CGD
13: 169–185
Julio C. Espinosa-Lara, Diana Guzman-Villanueva, Jenniffer I. Arenas-Garcı´a, Dea Herrera-Ruiz, Jesu´s Rivera-Islas, Perla Roma´nBravo, Hugo Morales-Rojas, and Herbert H€ opfl
Cocrystals of active pharmaceutical ingredients—praziquantel in combination with oxalic, malonic, succinic, maleic, fumaric, glutaric, adipic, and pimelic acids
13: 2098–2106 Yang-Hui Luo and Bai-Wang Sun
Pharmaceutical cocrystals of pyrazinecarboxamide with various carboxylic acids: crystallography, Hirshfeld surfaces, and dissolution study
Pyrimethamine
2013 CEC
15: 2916–2928 Amit Delori, Peter T.A. Galek, Elna Knowledge-based hydrogen bond Pidcock, Mohit Patni, and William prediction and the synthesis of salts Jones and cocrystals of the anti-malarial drug pyrimethamine with various drug and GRAS molecules
Quinoline
2012 CEC
14: 1967–1971 Sa´ndor L. Bek€ o, Martin U. Schmidt, An experimental screen for and Andrew D. Bond quinoline/fumaric acid salts and cocrystals
Ribavirin
2014 CGD
14: 6399–6408 Jia-Mei Chen, Song Li, and Tong-Bu Lu
Salicylic acid
2014 CGD
14: 2893–2899 Kyeong-Sill Lee, Kwang-Joo Kim, In situ monitoring of and Joachim Ulrich cocrystallization of salicylic acid– 4,40 -dipyridyl in solution using Raman spectroscopy
Pharmaceutical cocrystals of ribavirin with reduced release rates
Continued
ARTICLE IN PRESS
Pyrazinecarboxamide 2013 CGD
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2014 CEC
16: 5887–5896 Fabrizia Grepioni, Johan Wouters, Dario Braga, Saverio Nanna, Baptiste Fours, Gerard Coquerel, Geraldine Longfils, Sandrine Rome, Luc Aertse, and Luc Quere
Sildenafil
2014 CEC
16: 32–35
Stanozolol
2014 CGD
14: 3408–3422 Anae¨lle Tilborg, Geraldine Springuel, Bernadette Norberg, Johan Wouters, and Tom Leyssens
Sulfacetamide
2014 CEC
16: 5859–5869 N. Rajesh Goud, Ronaq Ali Khan, Modulating the solubility of and Ashwini Nangia sulfacetamide by means of cocrystals
Sulfathiazole
2014 CGD
14: 803–813
Tadalafil
2012 CEC
14: 2377–2380 David R. Weyna, Miranda L. Cheney, Ning Shan, Mazen Hanna, Lukasz Wojtas, and Michael J. Zaworotko
ˇ egarac, Edislav Leksˇic, Miroslav Z Primozˇ Sˇket, Janez Plavec, Maja Devcic Bogdanovic, DejanKresˇimir Bucar, Miljenko Dumic, and Ernest Mesˇtrovic
Ionic cocrystals of racetams: solidstate properties enhancement of neutral active pharmaceutical ingredients via addition of Mg2+ and Ca2+ chlorides A sildenafil cocrystal based on acetylsalicylic acid exhibits an enhanced intrinsic dissolution rate
How cocrystallization affects solidstate tautomerism: stanozolol case study
Yun Hu, Katarzyna Gniado, Andrea Mechanochemical reaction of Erxleben, and Patrick McArdle sulfathiazole with carboxylic acids: formation of a cocrystal, a salt, and coamorphous solids Crystal engineering of multiplecomponent organic solids: pharmaceutical cocrystals of tadalafil with persistent hydrogen bonding motifs
ARTICLE IN PRESS
Seletracetam
2014 CGD
14: 6557–6569 Srinivasulu Aitipamula, Pui Shan Chow, and Reginald B.H. Tan
Crystal engineering of tegafur cocrystals: structural analysis and physicochemical properties
Telmisartan
2014 CEC
16: 8375–8389 Renu Chadha, Swati Bhandari, Jamshed Haneef, Sadhika Khullar, and Sanjay Mandal
Cocrystals of telmisartan: characterization, structure elucidation, in vivo and toxicity studies
Temozolomide
2013 CGD
13: 2208–2219 Palash Sanphui, N. Jagadeesh Babu, Temozolomide cocrystals with and Ashwini Nangia carboxamide coformers
Tenoxicam
2013 CGD
Theophylline
2012 CEC
13: 1988–2003 Geetha Bolla, Palash Sanphui, and Solubility advantage of tenoxicam Ashwini Nangia phenolic cocrystals compared to salts ˚ ke C. Rasmuson The theophylline–oxalic acid 14: 4644–4655 Shuo Zhang and A cocrystal system: solid phases, thermodynamics and crystallisation
Theophylline
2012 CEC
14: 5128–5129 Sebastian Heiden, Lisa Tr€ obs, Klaus-J€ urgen Wenzel, and Franziska Emmerling
Mechanochemical synthesis and structural characterisation of a theophylline-benzoic acid cocrystal (1:1)
Theophylline
2012 CEC
14: 6163–6169 Heba Abourahma, Jennifer M. Urban, Nicole Morozowich, and Benny Chan
Examining the robustness of a theophylline cocrystal during grinding with additives Continued
ARTICLE IN PRESS
Tegafur
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d Compound Year Journal Volume: pages Authors Title
2013 CGD
˚ ke C. Rasmuson Thermodynamics and crystallization 13: 1153–1161 Shuo Zhang and A of the theophylline–glutaric acid cocrystal
Theophylline
2013 AAPSPST
14: 265–276
Theophylline
2014 CGD
14: 5318–5328 Dejan-Kresˇimir Bucar, Rodger F. Henry, Geoff G.Z. Zhang, and Leonard R. MacGillivray
Synthon hierarchies in crystal forms composed of theophylline and hydroxybenzoic acids: cocrystal screening via solution-mediated phase transformation
Theophylline
2014 CEC
16: 3141–3147 Ping Li, Yueying Chu, Lin Wang, Robert M. Wenslow, Jr., Kaichao Yu, Hailu Zhang, and Zongwu Deng
Structure determination of the theophylline–nicotinamide cocrystal: a combined powder XRD, 1D solid-state NMR, and theoretical calculation study
Theophylline
2014 JPS
103: 2859–2864
An investigation of the causes of cocrystal dissociation at high humidity
Amjad Alhalaweh, Waseem Kaialy, Theophylline cocrystals prepared by Graham Buckton, and Hardyal Gill spray drying: physicochemical properties and aerosolization performance
Mark D. Eddleston, Ranjit Thakuria, Barry J. Aldous, and William Jones
ARTICLE IN PRESS
Theophylline
2014 JPBA
100: 322–328
Edyta Pindelska, Agnieszka Sokal, Solid-state NMR studies of Lukasz Szeleszczuk, Dariusz Maciej theophylline cocrystals with Pisklak, and Waclaw Kolodziejski dicarboxylic acids
Tolfenamic acid
2014 CEC
16: 8252–8262 K. Gaglioti, M.R. Chierotti, F. Improvement of the water solubility Grifasi, R. Gobetto, U.J. of tolfenamic acid by new multipleGriesser, D. Hasa, and D. Voinovich component crystals produced by mechanochemical methods
Tranilast
2013 CGD
13: 3546–3553 Na Geng, Jia-Mei Chen, Zi-Jian Li, Approach of cocrystallization to Long Jiang, and Tong-Bu Lu improve the solubility and photostability of tranilast
Trithiocyanuric acid 2014 CGD
14: 4803–4810 V. Nagarajan and Venkateswara Rao Preparation of multiple cocrystals of Pedireddi trithiocyanuric acid with some N-donor compounds
Trospium chloride
2014 CGD
14: 2931–2936 Veronika Sla´dkova´, Jana Cibulkova´, Application and comparison of Va´clav Eigner, Antonı´n Sˇturc, cocrystallization techniques on Bohumil Kratochvı´l, and Jan trospium chloride cocrystals Rohlı´cek
Voriconazole
2014 CEC
16: 4722–4731 S. Sudalai Kumar, Ranjit Thakuria, Pharmaceutical cocrystals and a and Ashwini Nangia nitrate salt of voriconazole
Vorinostat
2012 CEC
14: 362–365
Cristina Puigjaner, Rafael Barbas, A cocrystal is the key intermediates Anna Portell, Ismael Valverde, for the production of a new Xavier Vila, Xavier Alcobe, Merce` polymorph of Vorinostat Font-Bardia, and Rafel Prohens Continued
ARTICLE IN PRESS
Theophylline
Table 1 Compilation of papers published during 2012–2014 whose subject matter comprises cocrystal systems of pharmaceutical interest— cont’d
Journal abbreviations AAPS PharmSciTech
AC
Acta Crystallographica
CEC
CrystEngComm
CGD
Crystal Growth & Design
CPB
Chemical Pharmaceutical Bulletin
CS
Chemical Science
EJPS
European Journal of Pharmaceutical Sciences
IJP
International Journal of Pharmaceutics
JMS
Journal of Molecular Structure
JPBA
Journal of Pharmaceutical and Biomedical Analysis
JPS
Journal of Pharmaceutical Sciences
ARTICLE IN PRESS
AAPS-PST
ARTICLE IN PRESS Cocrystal Systems of Pharmaceutical Interest: 2012–2014
29
of publication. For each entry, the table also contains the bibliographic citation to the paper, a complete list of the authors, and the title of the paper. Although every attempt has been to do so, the coverage described herein cannot be represented as being encyclopedic or comprehensive. Apologies are rendered in advance to any scientist in the field whose works have been inadvertently omitted.
References [1] H.G. Brittain, Pharmaceutical cocrystals: the coming wave of new drug substances, J. Pharm. Sci. 102 (2013) 311–317. [2] O. Almarsson, M.L. Peterson, M. Zaworotko, The A to Z of pharmaceutical cocrystals: a decade of fast-moving new science and patents, Pharm. Pat. Anal. 1 (3) (2012) 313–327. [3] N. Blagden, S.J. Coles, D.J. Berry, Pharmaceutical cocrystals—are we there yet? CrstEngComm 16 (2014) 5753–5761. [4] C.B. Aaker€ oy, S. Forbes, J. Desper, Altering physical properties of pharmaceutical cocrystals in a systematic manner, CrstEngComm 16 (2014) 5870–5877. [5] D.P. Elder, R. Holm, H. Lopez de Diego, Use of pharmaceutical salts and cocrystals to address the issue of poor solubility, Int. J. Pharm. 453 (2013) 88–100. [6] R. Thakuria, A. Deloria, W. Jones, M.P. Lipert, L. Roy, N. Rodrı´guez-Hornedo, Pharmaceutical cocrystals and poorly soluble drugs, Int. J. Pharm. 453 (2013) 101–125. [7] H.G. Brittain, Cocrystal systems of pharmaceutical interest: 2007–2008, in: H.G. Brittain (Ed.), Chapter 9: Profiles of Drug Substances, Excipients, and Related Methodology, vol. 35, Elsevier Academic Press, Amsterdam, 2010, pp. 373–390. [8] H.G. Brittain, Cocrystal systems of pharmaceutical interest: 2009, in: H.G. Brittain (Ed.), Chapter 10: Profiles of Drug Substances, Excipients, and Related Methodology, vol. 35, Elsevier Academic Press, Amsterdam, 2011, pp. 361–381. [9] H.G. Brittain, Cocrystal systems of pharmaceutical interest: 2010, Cryst. Growth Des. 12 (2012) 1046–1054. [10] H.G. Brittain, Cocrystal systems of pharmaceutical interest: 2011, Cryst. Growth Des. 12 (2012) 5823–5832.