Pharmaceutical cocrystals of the anti-tuberculosis drug pyrazinamide with dicarboxylic and tricarboxylic acids

Wang, Jian‐Rong; Ye, Chanjuan; Zhu, Bi‐Xue; Zhou, Chuanjiang; Mei, Xuefeng

doi:10.1039/c4ce02044h

Cited by 52 publications

(36 citation statements)

References 23 publications

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“…The anti-tuberculosis pharmaceuticals pyrazinamide (PYR) and ethionamide (ETH) are structurally similar and comprise both hydrogen-bond donor and acceptor sites. The ability of the drugs to form multiple hydrogen bonds [ 65 , 66 ] makes them synthetically and structurally intriguing. The API PYR contains an amide and two aromatic nitrogen atoms as synthon handles ( figure 8 a ), and is frequently used in combination with other drugs, which can pose compatibility and bioavailability issues [ 65 ].…”

Section: Co-crystals Involving Pharmaceutical Compoundsmentioning

confidence: 99%

Functional materials based on molecules with hydrogen-bonding ability: applications to drug co-crystals and polymer complexes

Hutchins¹

2018

R. Soc. open sci.

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The design, synthesis and property characterization of new functional materials has garnered interest in a variety of fields. Materials that are capable of recognizing and binding with small molecules have applications in sensing, sequestration, delivery and property modification. Specifically, recognition of pharmaceutical compounds is of interest in each of the aforementioned application areas. Numerous pharmaceutical compounds comprise functional groups that are capable of engaging in hydrogen-bonding interactions; thus, materials that are able to act as hydrogen-bond receptors are of significant interest for these applications. In this review, we highlight some crystalline and polymeric materials that recognize and engage in hydrogen-bonding interactions with pharmaceuticals or small biomolecules. Moreover, as pharmaceuticals often exhibit multiple hydrogen-bonding sites, many donor/acceptor molecules have been specifically designed to interact with the drug via such multiple-point hydrogen bonds. The formation of multiple hydrogen bonds not only increases the strength of the interaction but also affords unique hydrogen-bonded architectures.

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Section: Co-crystals Involving Pharmaceutical Compoundsmentioning

confidence: 99%

Functional materials based on molecules with hydrogen-bonding ability: applications to drug co-crystals and polymer complexes

Hutchins¹

2018

R. Soc. open sci.

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“…S1-S5 of the supporting information. 2013; Lou et al, 2015;Wang et al, 2014Wang et al, , 2015Abourahma et al, 2011;Luo & Sun, 2013;Eddleston et al, 2016;Aree & Chaichit, 2009;Adalder et al, 2012;Aakerö y et al, 2004;Grobelny et al, 2011;Thakuria et al, 2012;Abourahma et al, 2015;McMahon et al, 2005;Thorat et al, 2015). From the structural analysis of the reported cocrystals it was observed that acid-pyridine (synthon I), acid-acid, amideamide and acid-amide dimers (synthon II, III and IV, respectively) are more common for cocrystals of Pyz containing coformers with acid functionality.…”

Section: Pyzá24dhbamentioning

confidence: 99%

First-line antituberculosis drug, pyrazinamide, its pharmaceutically relevant cocrystals and a salt

Sarmah

Rajbongshi

Bhowmick

et al. 2017

Acta Crystallogr B Struct Sci Cryst Eng Mater

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A few pyrazinamide (Pyz) cocrystals involving hydroxybenzoic/cinnamic acid derivatives [2,4-dihydroxybenzoic acid (24DHBA); 2,6-dihydroxybenzoic acid (26DHBA); 3,5-dihydroxybenzoic acid (35DHBA) and nutraceutical molecule ferulic acid (FRA)] and the first example of a molecular salt with p-toluenesulfonic acid (pTSA) have been prepared and characterized using various solid-state techniques. A high-temperature cocrystal polymorph of Pyz·FRA has been characterized from the endothermic peaks observed using differential scanning calorimetry. The presence of substituent groups carrying hydrogen bond donors or acceptors and their influence on supramolecular synthon formation has been investigated using a Cambridge Structural Database search. Equilibrium solubility of all the binary complexes of Pyz follows the order of their coformer solubility, i.e. Pyz·pTSA > Pyz·35DHBA > Pyz > Pyz·26DHBA > Pyz·24DHBA > Pyz·FRA. A twofold enhancement in solubility of Pyz·pTSA molecular salt compared with the parent drug suggests a potential drug formulation for the treatment of tuberculosis.

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“…Fumaric acid was chosen as a bridge to link isoniazid and pyrazinamide as the carboxylic acid functional groups in fumaric acid can interact effectively with N -heterocycles of isoniazid and pyrazinamide to form stronger heterosynthon [ 261 ]. Moreover, the amide functional group of pyrazinamide and hydrazide functional group in isoniazid has been reported to form hydrogen-bonding motifs with dicarboxylic acids and tricarboxylic acids in several studies [ 275 , 276 ]. The selection of suitable dicarboxylic acid plays an important role in determining the success of this ‘drug-bridge-drug ternary cocrystallization strategy’.…”

Section: Ternary and Quaternary Cocrystalsmentioning

confidence: 99%

Engineering Cocrystals of Poorly Water-Soluble Drugs to Enhance Dissolution in Aqueous Medium

2018

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Biopharmaceutics Classification System (BCS) Class II and IV drugs suffer from poor aqueous solubility and hence low bioavailability. Most of these drugs are hydrophobic and cannot be developed into a pharmaceutical formulation due to their poor aqueous solubility. One of the ways to enhance the aqueous solubility of poorlywater-soluble drugs is to use the principles of crystal engineering to formulate cocrystals of these molecules with water-soluble molecules (which are generally called coformers). Many researchers have shown that the cocrystals significantly enhance the aqueous solubility of poorly water-soluble drugs. In this review, we present a consolidated account of reports available in the literature related to the cocrystallization of poorly water-soluble drugs. The current practice to formulate new drug cocrystals with enhanced solubility involves a lot of empiricism. Therefore, in this work, attempts have been made to understand a general framework involved in successful (and unsuccessful) cocrystallization events which can yield different solid forms such as cocrystals, cocrystal polymorphs, cocrystal hydrates/solvates, salts, coamorphous solids, eutectics and solid solutions. The rationale behind screening suitable coformers for cocrystallization has been explained based on the rules of five i.e., hydrogen bonding, halogen bonding (and in general non-covalent bonding), length of carbon chain, molecular recognition points and coformer aqueous solubility. Different techniques to screen coformers for effective cocrystallization and methods to synthesize cocrystals have been discussed. Recent advances in technologies for continuous and solvent-free production of cocrystals have also been discussed. Furthermore, mechanisms involved in solubilization of these solid forms and the parameters influencing dissolution and stability of specific solid forms have been discussed. Overall, this review provides a consolidated account of the rationale for design of cocrystals, past efforts, recent developments and future perspectives for cocrystallization research which will be extremely useful for researchers working in pharmaceutical formulation development.

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Pharmaceutical cocrystals of the anti-tuberculosis drug pyrazinamide with dicarboxylic and tricarboxylic acids

Cited by 52 publications

References 23 publications

Functional materials based on molecules with hydrogen-bonding ability: applications to drug co-crystals and polymer complexes

Functional materials based on molecules with hydrogen-bonding ability: applications to drug co-crystals and polymer complexes

First-line antituberculosis drug, pyrazinamide, its pharmaceutically relevant cocrystals and a salt

Engineering Cocrystals of Poorly Water-Soluble Drugs to Enhance Dissolution in Aqueous Medium

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