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Cocrystals: A Review of Recent Trends in Pharmaceutical and Material

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DOI: 10.13005/msri/140103

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Material Science Research India Vol. 14(1), 09-18 (2017)

Cocrystals: A Review of Recent Trends in Pharmaceutical and

Material Science Applications
Manjunath G. Javoor1, Pradip Kumar Mondal2 and Deepak Chopra2*

Department of Chemistry, NITK, Surathkal, Mangalore 575025.

1

2
Department of Chemistry, Indian Institute of Science
Education and Research Bhopal, Bhauri, Bhopal 462066, India.
Corresponding author Email: dchopra@iiserb.ac.in

http://dx.doi.org/10.13005/msri/140103

(Received: May 29, 2017; Accepted: June 14, 2017)

Abstract

Over the last two decades, the design of multicomponent molecular crystals or cocrystals
has grown out to be an interesting and promising area of research in pharmaceuticals and material
science. Cocrystallization is at the interface of crystal engineering and supramolecular chemistry
and allows us to vary the physicochemical properties of solids according to the need, through
manipulation of various intermolecular interactions. In this short review, we focus on some recent
reports on pharmaceutical cocrystals and emerging subclasses of cocrystals, namely: Charge
transfer cocrystals, Energetic cocrystals, and Ternary cocrystals and discuss about their methods
of characterization and applications of importance in the industry.

Key words: Pharmaceutical cocrystals, Charge transfer cocrystals, Energetic

cocrystals, Ternary cocrystals, Physicochemical properties.

Introduction the framework of multicomponent crystal and

secondary, weaker interactions such as halogen
The advent of crystal engineering has bonds, van der Waals forces act as auxiliary scaffolds
transformed the pace of research in molecular to stabilize the framework12. Initially, cocrystals
solids. Attaining the desired properties in molecular have been exploited in pharmaceutical research
solids by controlled manipulation of intermolecular to alter the physicochemical properties of a drug
interactions holds the key to success in this such as bio availability, solubility, stability, melting
area of research. For that matter, strength and point and shelf life13,15. With this growing success
directionality of weak intermolecular interactions in pharmaceuticals16,17, cocrystallization as a tool
are important features to be taken into account. to alter the properties of solids is spreading into
Crystal engineering, through supramolecular research in material science. It is now being used
synthons, allows us to design cocrystals with desired in the design of organic functional materials and
physicochemical properties3,5. Cocrystallization6,8 energetic materials. Charge transfer cocrystals18,20
and polymorphism9,11 are two important applications have found a place in the design of optoelectronic
of crystal engineering. A cocrystal entails two or devices such as Field effect transistors (FETs),
more neutral molecules to be held together by diodes. Many of the energetic materials are highly
weak intermolecular interactions in a definite ratio. sensitive and possess low power and undesirable
Since intermolecular interactions guide properties detonation properties. Cocrystal formation of an
of molecular solids, cocrystal formation is of great energetic substance with suitable cocrystal former
interest to crystal engineers. Primary non-covalent can greatly alter its sensitivity and density (and
interactions such as strong hydrogen bonds decide hence the power)21,26. More recently, researchers
10 Javoor et al, Mat. Sci. Res. India, Vol. 14(1), 09-18 (2017)

have opened up a new class of cocrystals called pH. Recently, new cocrystals of Hydrochlorothiazide
ternary cocrystals, which involves binding of three (HCT) with piperazine (PPZ), tetramethylpyrazine
neutral molecular entities through weak interactions (TMPZ), picolinamide (PCM), malonamide (MAM),
which are interesting as well as challenging. Over isonicotinic acid (INIC), and with a tuberculosis
the years, cocrystallization has been used as a drug isoniazid (INZ) were reported33, among them
tool to vary the properties of a solid and hence this HCT-PPZ showed seven-fold increase in solubility
area has generated a lot of interest and attention. (Figure 1). Permeability is another important
With the help of crystal structure prediction (CSP), property of an API which depends on absorption of
it is now possible to know the crystal structure and the drug on the cell membrane. Both solubility and
motifs involved in the framework of cocrystals27. A permeability were enhanced in the case of HCT-PPZ
crystal engineer can have an idea if the experiments which is essential for bioavailability of the drug. It
involving high-cost drug molecules and other can be clearly seen that cocrystals always need not
compounds will yield fruitful results. Here we present have a higher solubility than the drug (HCT-MAM and
a brief review of pharmaceutical and material science HCT-TMPZ have solubilities lower than HCT).
applications of cocrystals.
The diûusion behavior of the new solid
Pharmaceutical cocrystals forms of HCT was studied using a Franz diûusion
A pharmaceutical cocrystals a cell, the plot of ûux of the drug at the time indicate
homogeneous crystalline entity which contains that HCT”PPZ and HCT”PCM cocrystals exhibit
an active pharmaceutical ingredient (API) and a better diûusion behavior among all the cocrystals
cocrystal former (GRAS molecule) in a stoichiometric (Figure 2). It is suggested that coformers that
ratio, in the same crystal lattice stabilized by non- cause higher solubility in cocrystals lead to higher
covalent interactions such as hydrogen bonds, p- p diffusion.
interactions, ionic interactions, and van der Waals
forces28,30. The majority of the drug molecules in the Our group has reported ten different
market are sold out in their salt forms, and some cocrystals,one polymorph of a cocrystal and a
molecules, though potential drug candidates, cannot salt of an organofluorine drug riluzole with various
form salts due to the absence of ionizable sites in carboxylic acids and pyridine derivatives 12. The
the molecule. Cocrystallization comes in handy in new crystalline phases are stabilized by primary
such cases, which allows us to use them as neutral and secondary intermolecular interactions, with
molecules along with coformers without loss of a melting point range between 90-1400C closely
biological activity. related to MP of original API (118°C). Cocrystals
exhibited enhanced solubility and dissolution rate in
The majority of the drugs are ineffective in comparison to riluzole12. The structure of compounds
their bioactivity due to low solubility and permeability, used in the study and the plot of the cumulative
which limits their clinical applications. Over the amount of cocrystal dissolved against time is given
years, cocrystallization is widely used in the field of in Figure 3a and 3b respectively.
pharmaceuticals for improving the physicochemical
properties of the drug molecules such as solubility, Charge Transfer cocrystals
bioavailability, permeability, stability, melting point Single component organic materials used
and shelf life 31,32. Because of the simple and in designing organic semiconductors have attained
profitable methods involved in designing a cocrystal, limited success. Organic cocrystals involving
and performance, it is now a most viable method for ordered stacking of donors and acceptors offer
improving the physicochemical properties of drugs. It unique physicochemical properties which are
is to be noted that, there is no particular method to desirable for applications in optoelectronic devices
design cocrystals of all the drugs. The strategy which (like Field Effect Transistors and optical diodes)34,35.
works for one may not work for the other; each drug This has led to growing interest in yet another
has to be dealt separately keeping the property to be nascent subclass of cocrystals, namely, charge
varied in mind. The solubility of a drug depends on transfer cocrystals which have greater implications
melting point, dielectric constant, temperature, and for designing optoelectronic devices. The most
 Javoor et al, Mat. Sci. Res. India, Vol. 14(1), 09-18 (2017) 11

important factor as far as charge transfer cocrystals derivatives (Figure 6). Fluorine derivatives have
are concerned is ionicity or degree of charge transfer strong acceptor abilities than TCNQ, leading to
between a donor (D) and an acceptor (A). Ionicity greater ionicity of CT interactions formed.
or degree of CT is directly related to conducting
ability36,37 and lattice instability38 of cocrystals. As of Very recently, Prof A. J. Matzger and co-
now, there exists no particular method for confirming workers have demonstrated the role of hydrogen
the degree of charge transfer, and its elusive nature bonding and halogen bonding on the packing and
requires further research in this area. Hu et al, have ionicity of CT- cocrystals [44]. They have synthesized
reported a novel, 2-D light emitting charge transfer CT cocrystals using 1, 5-diaminonaphthalene (DAN)
(1:1) cocrystal of a 1,2-di(4-pyridyl)ethylene (Bpe) as the donor and halogen substituted benzoquinones
and 1,2,4,5-tetracyanobenzene (TCNB) molecules (XA, X= F, Cl, Br, I) as acceptors (Figure 7a). A
(Figure 4)39. comparison of the HOMO and LUMO energies of
DAN (donor) and XA (acceptor) molecules is given
They have noted that “To the best of our in Figure 7b.
knowledge, the CT nature of crystals of Donor-
Acceptor complexes is difficult to verify accurately.” In this work, the dependence of the degree
Both spectroscopic and theoretical methods were of ionization of cocrystal on electronegativity of the
used to confirm the charge transfer nature in BPe- halogen substituent was demonstrated experimentally
TCNB cocrystals. Xu et al18 have demonstrated by using Raman spectroscopy. For this study, anion
the role of solvents in controlling the molar ratio radicals of CA and BA were synthesized and were
subjected to Raman spectroscopy along with CA,
and different charge transfer interaction modes
BA, DAN”CA cocrystal and DAN”BA cocrystal. The
by studying 1-phenyl-3-(pyren-1yl) prop-2-en-1-
corresponding carbonyl peak in each spectrum (CA
one (PPPO) as electron donor (D) and 7,7,8,8- = 1689.7 cm”1, CA•” = 1588.2 cm”1 and DAN”CA =
tetracyanoquinodimethane (TCNQ) as electron 1663.3 cm”1; BA = 1681.3 cm”1, BA•” = 1582.3 cm”1
acceptor (A) to form CT complexes (Figure 5)18. and DAN”BA = 1657.7 cm”1 (Figure 8a and 8b) was
used to estimate ñ(ionicity) for both cocrystals. The
In recent years, the design of charge transfer more electronegative chlorine (3.0) substituted
cocrystals involving the use of conjugated aromatic DAN”CA has an ionicity value of 0.27 e, and the less
hydrocarbons as electron donors and halogenated electronegative bromine (2.8) substituted DAN”BA
acceptors finds applications in electronics and has an ionicity value of 0.23 e, showing the direct
photonics40,42. Due to its excellent eûciency and relation between ionicity and electronegativity of
halogen substituent.
stability of assembling cocrystals with electron
donors, TCNQ is one of the most widely used
Energetic cocrystals
acceptors in the field of CT complexes. Recently,
Energetic materials, a class of materials
E. D. Como and coworkers43 have synthesized CT
which includes explosives, propellants and
cocrystals of perylene with TCNQ and its fluorine
pyrotechnics suffer from undesirable properties such

Fig. 1: a) Structure of HCT and coformers. b) Comparison of solubility of HCT and cocrystals.
Asterisk mark denotes solubility after 4h(Reproduced with permission from reference 33.
Copyright 2017 American Chemical Society).
12 Javoor et al, Mat. Sci. Res. India, Vol. 14(1), 09-18 (2017)

as poor stability, high sensitivity and low density(

hence, low explosive power) which have limited
their applications. Traditionally, the development
and optimisation of properties of energetic materials
was dependent on synthetic methods. In recent
years, crystal engineering through cocrystallization
has paved new ways to alter the physicochemical
properties of energetic materials very efficiently.
Cocrystallization offers a robust method for attaining
desired sensitivity, stability, and high power energetic
materials without requiring synthesis of new
Fig. 2: Plot of Flux/permeability of cocrystals compounds.
of HCT vs. time(Reproduced with permission
from reference 33. Copyright 2017 American A particular class of energetic materials,
Chemical Society) azoles are of great interest from the point of crystal

Fig. 3: a) Structure of the drug riluzole and coformers used in the study. b) The intrinsic
dissolution rateMeasurements of riluzole cocrystals and salt in pH 7 buffer medium(Reproduced
with permission from reference 12. Copyright 2017 American Chemical Society).

Fig. 4: a) Structure of trans-Bpe, TCNB, and

the molecular structure Bpe-TCNB complex
obtained. b) The self-assembly intermolecular Fig. 5: The intermolecular π•••π and C-H•••π
interactions involved (π•••π, D•••A, and interactions involved in CT complexes I and
C-H•••N)(Reproduced with permission from II(Reproduced with permission from reference
reference 39. Copyright 2015John Wiley and 18. Copyright 2015 American Chemical
Sons). Society).
 Javoor et al, Mat. Sci. Res. India, Vol. 14(1), 09-18 (2017) 13

Fig. 6: Structural motifs of (a) perylene:TCNQ (1:1), (b) perylene:TCNQ(3:1), (c) perylene: TCNQ-
F2 (1:1), (d) perylene:TCNQ-F2 (3:2), (e) perylene:TCNQ-F4 (1:1), and (f) perylene:TCNQ-F4 (3:2)
(Reproduced with permission from reference 43. Copyright 2016 American Chemical Society).

Fig. 7: a) Structures of donor and acceptors used in CT cocrystal synthesis. b) A Comparison

Fig. 8: (a) Raman spectra (Stacked) of the pure component CA, CA radical anion, and cocrystal
(CA-DAN). The carbonyl peak used to estimate ionicity is marked by the red ring. (b) Raman
spectra of the BA pure component, BA radical anion, and DAN−BA cocrystal. The carbonyl peak
used to estimate ionicity is marked by the red ring(Reproduced with permission from reference
44. Copyright 2017 American Chemical Society).
14 Javoor et al, Mat. Sci. Res. India, Vol. 14(1), 09-18 (2017)

engineering as they possess hydrogen bond the cocrystals prepared have the power of pure
donors (primary and secondary amines in aromatic components with decreased impact sensitivity
systems). Matzger and coworkers have reported a which can be attributed to the hydrogen bonding
series of three cocrystals of 5,52 -Dinitro2H,2H2 interactions in the cocrystals.
-3,32 -bi-1,2,4-triazole (DNBT), which is a high-
density azole explosive, which has limited military Another area of concer n regarding
applications23. The structures of DNBT and three energetic materials is their sensitivity towards
coformers: 5-amino-3-nitro-1H-1,2,4-triazole external stimuli which hampers storage and handling.
(ANTA), 1H,4H-3,6-dinitropyrazolo[4,3-c]pyrazole Currently, there are two methods available for loading
(DNPP), and 3,4-dinitropyrazole (3,4-DNP), and the the energetic materials into munitions: a) melting and
hydrogen bond motifs utilized in cocrystal formation casting, b) hydraulic pressing26. The former method
are given below in Figure 9. is more advantageous than the latter in terms of
reduction of void space and greater processing
Further, packing coefficient (Ck) which is a efficiency.
measure of the density of an energetic material, is
estimated (Figure 10a), and the detonation velocities Matzger et al have designed an energetic
of all the three cocrystals were determined using cocrystal of 3, 4-diaminofurazan (DAF) and
Cheetah 6.0 software at 298K (Figure 10b)23. All 4-amino-3,5-dinitropyrazole(ADNP) is melt castable,

Fig. 9: Structures of DNBT and coformers and crystal structure of hydrogen bond motifs involved
(numbers 1, 2, and 3 represent cocrystals of DNBT with ANTA, DNPP, and 3,4-DNP respectively)
(Reproduced with permission from reference 23. Copyright 2015 American Chemical Society).

Fig. 10: a) Packing coefficients/ densities (Ck) of all the pure components and DNBT cocrystal 1−3
are calculated from the room-temperature (298 K) crystal lattices of each material. b) Detonation
velocities of each pure component and DNBT cocrystal 1−3.(Reproduced with permission from
reference 23. Copyright 2015 American Chemical Society)
15 Javoor et al, Mat. Sci. Res. India, Vol. 14(1), 09-18 (2017)

a proper ty which is not possessed by pure pressure) using Cheetah 7.0 software indicates the
components25. The structure of compounds used high performance of ADNP/DAF cocrystal, which is
and hydrogen bonding interactions is given (Figure intermediate in comparison to the pure components
11a and 11b respectively). It is known that a good (Figure 11d).
melt castable material must possess, a low melting
point, large range between the melting point and the There is limited literature available on
start of decomposition, and high loading density26. cocrystallization of energetic materials as this is a
As observed from DSC curves of 1, ADNP and DAF new area yet to be ventured into. Cocrystallization
(Figure 11c), the cocrystal 1 has a melting point as a tool to vary the properties of energetic materials
around 172ÚC, which is lower than both ADNP has gained attention in recent years. We hope to see
and DAF. Further, there is a large difference in more reports in this area in the coming years.
melting point and starting of decomposition, which
is absent in ADNP. Thus, it qualifies to be a melt Ternary cocrystals
castable energetic material. In addition, theoretical So far, we discussed about cocrystals
estimation of detonation parameters (velocity and involving two components and their importance.

Fig. 11: a) Structures of componds used in the study. b) Hydrogen bonding between DAF
and ADNP. c) DSC traces of 1:1 cocrystal DAF/ADNP (1), pure components ADNP and DAF.
d) Detonation parameters (velocity and pressure) of DAF, ADNP, 1 and TNT(Reproduced with
permission from reference 25. Copyright 2017Royal Society of Chemistry).

Fig. 12: (a) Hydrogen bonded motifs in SMBA–

NAM–2HP (1:1:1) and (b) SMBA–NAM–MeHP Fig. 13: The crystal packing in ternary
(1:1:1) involving the amide–amide heterodimer cocrystals of 4-nitrobenzene: oxalic acid:
and acid-pyridine synthons(Reproduced with 1,4-diiodo-benzene (2:1:1). Color code: acid-
permission from reference 46. Copyright amide (green); I•••O2N (pink). (Reproduced
2015Royal Society of Chemistry) with permission from reference 45. Copyright
2013Royal Society of Chemistry)
16 Javoor et al, Mat. Sci. Res. India, Vol. 14(1), 09-18 (2017)

A large volume of literature is available on binary functional groups46. Two of which are shown in Figure
cocrystals. Two component molecular crystals 12.
are comparatively easy to synthesize and are In their work on designing ternary cocrystals
established in terms of design and assembly45,46. using hydrogen and halogen bonds, G.R. Desiraju
Ternary cocrystals is a recent advancement in crystal and coworkers have carefully noted: “a balance
engineering and are yet to be established, hence
of interactions and solubilities is needed to get
there is lot of room for optimization of strategies for
a ternary cocrystal” 45. 2:1:1 Ternary cocrystals
designing ternary cocrystals. A ternary cocrystal is
an assembly of three neutral solid compounds in a of 4-nitrobenzamide: diacid: 1, 4-dihalogenated
single crystal structure through hydrogen bonding benzene was designed by graded selection of
and other weak interactions46. On moving from hydrogen and halogen bonds (Figure 13).
binary to a ternary system, there are a number of
ways in which three components can assemble Conclusions
themselves in a single crystal lattice. This makes
the process of design extremely difficult and In conclusion, cocrystallization has become
challenging. Added to this, availability of specific a very useful tool for a crystal engineer to modulate
and universal interactions may lead to the formation the properties of solid state materials. Recent
of polymorphs47,50 of individual molecules, binary developments in this area such as CT cocrystals,
cocrystals, solvatomorphs, etc. This renders energetic cocrystals, and ternary cocrystals are
design of ternary cocrystals more challenging. yet to be established. As of now, the results of
Desiraju and coworkers have carefully noted: applications of cocrystallization in pharmaceuticals
‘‘Making a stoichiometric ternary cocrystal from are fruitful only at microscopic level. Strategies to
three substances that are all solids under ambient produce cocrystals in larger scales are yet to be
conditions is far more diûcult and demands a good ventured into, in order to yield fruitful results of
knowledge of the interaction preferences’’ 45. A whatever has been achieved at microscopic level.
proper balance between intermolecular interactions Needless to say, in the coming year’s research in
and crystallization is necessary to obtain a ternary this area would be more focused on scaling up
cocrystal. Ternary cocrystals provide a viable processes.
alternative to vary the physicochemical properties
where binary cocrystals fail to do so. Acknowledgements

In 2015, A. Nangia and coworkers reported MGJ thanks NITK Surathkal. PKM thanks
five novel ternary cocrystals of p-sulfonamide CSIR for the senior research fellowship. DC
benzoic acid (SMBA) with pyridine amides and thanks, DST-SERB Scheme for funding. We are
lactam coformers by exploiting supramolecular thankful to IISER Bhopal for research facilities and
synthons of the carboxylic acid and sulfonamide
infrastructure.

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