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

Liao, Xiangmin; Gautam, Mohan; Grill, Andreas; Zhu, Haijian

doi:10.1002/jps.21824

Cited by 40 publications

(38 citation statements)

References 16 publications

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“…Cocrystallization has recently gained great attention as an attractive method to obtain new forms of active pharmaceutical ingredients (APIs) with improved physical and physicochemical properties of drugs [1][2][3][4][5][6]. Cocrystal design for a specific API is based on evaluating possible synthons with reliable hydrogen bonding motifs (intermolecular interactions) sustaining crystal structures or other non-covalent and nonionic interactions within APIs and cocrystal formers (CCFs).…”

Section: Introductionmentioning

confidence: 99%

“…The presence of functional groups acting as hydrogen bond donors and acceptors in the molecules of APIs and CCFs may lead to the formation of cocrystallized substances. Cocrystallization is particularly important in the pharmaceutical field as a result of its impact on drug candidate performance, such as solubility, physical and chemical stability, melting point, and bioavailability of APIs, whereas the pharmacological activity of the APIs is generally not influenced [4,5].…”

Section: Introductionmentioning

confidence: 99%

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Raman and Terahertz Spectroscopic Investigation of Cocrystal Formation Involving Antibiotic Nitrofurantoin Drug and Coformer 4-aminobenzoic Acid

Cai

Xue

et al. 2016

Crystals

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Cocrystallization could improve most physicochemical properties of specific active pharmaceutical ingredients, which has great potential in pharmaceutical development. In this study, the cocrystal of nitrofurantoin and 4-aminobenzoic acid was prepared with solid-state (solvent-free or green-chemistry) grinding approach, and the above cocrystal has been characterized by Raman and terahertz vibrational spectroscopic techniques. Spectral results show that the vibrational modes of the cocrystal within the whole spectral region are different from those of the corresponding parent materials. The dynamic process of such pharmaceutical cocrystal formation has also been monitored directly with Raman spectra. These results offer us unique means for characterizing the cocrystal conformation from the molecule-level, and provides us with rich information about the reaction dynamic of cocrystal formation within pharmaceutical fields.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Raman and Terahertz Spectroscopic Investigation of Cocrystal Formation Involving Antibiotic Nitrofurantoin Drug and Coformer 4-aminobenzoic Acid

Cai

Xue

et al. 2016

Crystals

View full text Add to dashboard Cite

show abstract

“…Cocrystallizaiton has recently gained great attention as an attractive method to obtain new forms of active pharmaceutical ingredients (APIs) with improved physical and physicochemical properties of drugs [1][2][3][4][5][6]. Cocrystal design for a specific API is based on evaluating possible synthons with reliable hydrogen bonding motifs (intermolecular interactions) sustaining crystal structures or other non-covalent and nonionic interactions within APIs and cocrystal formers (CCFs).…”

Section: Introductionmentioning

confidence: 99%

“…The presence of functional groups acting as hydrogen bonds donors and acceptors in the molecules of APIs and CCFs may lead to the formation of cocrystallized substances. Cocrystallizaiton is particularly important in the pharmaceutical fields as a result of its impact on drug candidate performance, such as solubility, physical and chemical stability, melting point, as well as bioavilability of APIs, whereas the pharmacologic activity of the APIs is generally not influenced [4,5].…”

Section: Introductionmentioning

confidence: 99%

“…Traditional techniques that could be employed include powder X-ray diffractormetry (PXRD) [5,[16][17][18]22], thermal analysis such as differential scanning calorimetry (DSC), and also solid-state nuclear magnetic resonance spectroscopy (ss-NMR) [19][20][21][22]. These established techniques are sometimes time consuming or lack in specific structural information about the crystalline and/or molecules, especially the effect from the intra-molecular and weak inter-molecular interactions.…”

Section: Introductionmentioning

confidence: 99%

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Raman and Terahertz Spectroscopic Investigation of Cocrystal Formation Involving Antibiotic Nitrofurantoin Drug and Coformer 4-aminobenzoic Acid

Cai

Xue

et al. 2016

Preprint

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Cocrystallizaiton could improve most physicochemical properties of specific active pharmaceutical ingredients, which has great potential in pharmaceutical development. In this study, the cocrystal of nitrofurantoin and 4-aminobenzoic acid was prepared with solid-state (solvent-free or green-chemistry) grinding approach, and the above cocrystal has been characterized by Raman and terahertz vibrational spectroscopic techniques. Spectral results show that the vibrational modes of the cocrystal within the whole spectral region are different from those of the corresponding parent materials. The dynamic process of such pharmaceutical cocrystal formation has also been monitored directly with Raman spectra. These results offer us unique means for characterizing the cocrystal conformation from molecule-level and also provide us rich information about the reaction dynamic of cocrystal formation within pharmaceutical fields.

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Novel Glutaric Acid Cocrystal Formation via Cogrinding and Solution Crystallization

et al. 2013

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An efficient and reliable approach to discover new pharmaceutical cocrystals in the early development stage is proposed and used to develop cocrystals of piracetam with some aliphatic diacids. A 1:1 cocrystal of piracetam and glutaric acid was screened by a mechanochemical method and identified by powder X‐ray diffraction and differential scanning calorimetry. Followed by solution crystallization, this cocrystal was reproduced. To better understand the mechanism of cocrystal formation in solution crystallization, process analytical technologies including focused beam reflectance measurement, attenuated total reflectance‐Fourier transform infrared, and particle vision measurement were applied to investigate the cocrystallization process of piracetam with glutaric acid. The mechanism of cocrystal formation during solution‐mediated phase transformation is discussed in detail.

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

Cited by 40 publications

References 16 publications

Raman and Terahertz Spectroscopic Investigation of Cocrystal Formation Involving Antibiotic Nitrofurantoin Drug and Coformer 4-aminobenzoic Acid

Raman and Terahertz Spectroscopic Investigation of Cocrystal Formation Involving Antibiotic Nitrofurantoin Drug and Coformer 4-aminobenzoic Acid

Raman and Terahertz Spectroscopic Investigation of Cocrystal Formation Involving Antibiotic Nitrofurantoin Drug and Coformer 4-aminobenzoic Acid

Novel Glutaric Acid Cocrystal Formation via Cogrinding and Solution Crystallization

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