Three new hydrochlorothiazide cocrystals: Structural analyses and solubility studies

Ranjan, Subham; Devarapalli, Ramesh; Kundu, Soumya; Vangala, Venu R.; Ghosh, Animesh; Reddy, C. Malla

doi:10.1016/j.molstruc.2016.12.019

Cited by 49 publications

(32 citation statements)

References 48 publications

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“…40,41 It reveals that PXRD and simulated patterns match well at low 2q values than at high 2q values because of temperature difference for data collection of PXRD (298 K) and simulated patterns (200 K), and such observations were reported elsewhere for other compounds. 49 In comparison to slow crystallization method, there is relatively less probability of transformation of metastable to stable form during rotary evaporation as the solvent is removed rapidly from the mother liquor.…”

Section: Physical Characterizationmentioning

confidence: 99%

Thermodynamic Investigation of Carbamazepine-Saccharin Co-Crystal Polymorphs

Pagire

Jadav

Vangala

et al. 2017

Journal of Pharmaceutical Sciences

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Polymorphism in active pharmaceutical ingredients can be regarded as critical for the potential that crystal form can have on the quality, efficacy, and safety of the final drug product. The current contribution aims to characterize thermodynamic interrelationship of a dimorphic co-crystal, FI and FII, involving carbamazepine (CBZ) and saccharin (SAC) molecules. Supramolecular synthesis of CBZ-SAC FI and FII has been performed using thermokinetic methods and systematically characterized by differential scanning calorimetry, powder X-ray diffraction, solubility, and slurry measurements. According to the heat of fusion rule by Burger and Ramberger, FI (ΔH = 121.1 J/g; melting point, 172.5°C) and FII (ΔH = 110.3 J/g; melting point, 164.7°C) are monotropically related. The solubility and van't Hoff plot results suggest FI stable and FII metastable forms. This study reveals that CBZ-SAC co-crystal phases, FI or FII, could be stable to heat-induced stresses; however, FII converts to FI during solution-mediated transformation.

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Section: Physical Characterizationmentioning

confidence: 99%

Thermodynamic Investigation of Carbamazepine-Saccharin Co-Crystal Polymorphs

Pagire

Jadav

Vangala

et al. 2017

Journal of Pharmaceutical Sciences

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“…The instrument was equipped with a fine focus X-ray tube and each sample was placed on to goniometer head that was motorized to permit the spinning of the sample during data acquisition. The sample was scanned at 6 deg/min and voltage 40 Kv [15,16].…”

Section: X-ray Diffraction (Xrd)mentioning

confidence: 99%

Design, Formulation, and Characterization of Apremilast-Saccharin Cocrystals Loaded With Topical Gel

Mane¹,

Mohite²

2020

Asian J Pharm Clin Res

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Objective: Most of the drugs are relevant to BSC class II and class IV having solubility problems. Cocrystallization of drug with conformer is an immense approach used to explore the physicochemical properties of drug. The objective of the present work was to design formulate and evaluate the drug cocrystals of poorly soluble drug apremilast (APR) with saccharin. Methods: Cocrystals of APR were prepared using the solvent evaporation technique. The saturated solubility study and in vitro dissolution study of cocrystals were carried out. The prepared cocrystals were characterized by differential scanning calorimetry (DSC), X-ray diffraction (XRD), and Fourier-transform infrared (FTIR) spectroscopy. The topical gel of APR cocrystals was formulated optimized and evaluated using three-level factorial design. Results: The cocrystals of APR were prepared in 1:1 molar ratio with saccharin. APR cocrystals showed the improvement in solubility and dissolution as compared to pure APR. The formation of cocrystals was confirmed from change in endothermic peak of DSC and from shifting of FTIR spectra of cocrystals. Crystallinity of cocrystal was confirmed from XRD pattern and noteworthy change in 2θ values of the intense peak. The topical gel of APR cocrystals was formulated and optimized using three-level factorial design using Carbapol-940 and hydroxypropyl methylcellulose (HPMC) as a gelling agent. Conclusion: The cocrystals with altered physicochemical properties of APR were prepared with saccharin and formulated as a topical gel to overcome the problems related to oral administration.

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“…However, in both cases, the authors have not explored the concept of isomorphism. The present work reports the structural studies of new multicomponent solids of TFA or MFA with 4-dimethylaminopyridine (DMAP), which is known to form cocrystals/salts with APIs (Vangala et al, 2013;Ranjan et al, 2017a) in varying stoichiometric ratios. The concepts of solid-form screening, isostructurality, polymorphism and similarity in structural landscapes of related compounds are discussed.…”

Section: Introductionmentioning

confidence: 99%

Isomorphism: `molecular similarity to crystal structure similarity' in multicomponent forms of analgesic drugs tolfenamic and mefenamic acid

Ranjan

Devarapalli

Kundu

et al. 2020

IUCrJ

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The non-steroidal anti-inflammatory drugs mefenamic acid (MFA) and tolfenamic acid (TFA) have a close resemblance in their molecular scaffold, whereby a methyl group in MFA is substituted by a chloro group in TFA. The present study demonstrates the isomorphous nature of these compounds in a series of their multicomponent solids. Furthermore, the unique nature of MFA and TFA has been demonstrated while excavating their alternate solid forms in that, by varying the drug (MFA or TFA) to coformer [4-dimethylaminopyridine (DMAP)] stoichiometric ratio, both drugs have produced three different types of multicomponent crystals, viz. salt (1:1; API to coformer ratio), salt hydrate (1:1:1) and cocrystal salt (2:1). Interestingly, as anticipated from the close similarity of TFA and MFA structures, these multicomponent solids have shown an isomorphous relation. A thorough characterization and structural investigation of the new multicomponent forms of MFA and TFA revealed their similarity in terms of space group and structural packing with isomorphic nature among the pairs. Herein, the experimental results are generalized in a broader perspective for predictably identifying any possible new forms of comparable compounds by mapping their crystal structure landscapes. The utility of such an approach is evident from the identification of polymorph VI of TFA from hetero-seeding with isomorphous MFA form I from acetone-methanol (1:1) solution. That aside, a pseudopolymorph of TFA with dimethylformamide (DMF) was obtained, which also has some structural similarity to that of the solvate MFA:DMF. These new isostructural pairs are discussed in the context of solid form screening using structural landscape similarity.

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Three new hydrochlorothiazide cocrystals: Structural analyses and solubility studies

Cited by 49 publications

References 48 publications

Thermodynamic Investigation of Carbamazepine-Saccharin Co-Crystal Polymorphs

Thermodynamic Investigation of Carbamazepine-Saccharin Co-Crystal Polymorphs

Design, Formulation, and Characterization of Apremilast-Saccharin Cocrystals Loaded With Topical Gel

Isomorphism: `molecular similarity to crystal structure similarity' in multicomponent forms of analgesic drugs tolfenamic and mefenamic acid

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