Nitrofurantoin– p ‐aminobenzoic acid cocrystal: Hydration stability and dissolution rate studies

Cherukuvada, Suryanarayan; Babu, N. Jagadeesh; Nangia, Ashwini

doi:10.1002/jps.22546

Cited by 110 publications

(88 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The absorption spectra of grinding cocrystal distinguish at frequencies 1.05 and 1.40 THz, with pretty broader bands comparing with that of physical mixture. It is well-known that the cocrystallization occurs as the result of intermolecular hydrogen bonding, nonionic or other nonconvalent interactions between two or more molecules of the different components [14][15][16]. So the experimental results indicate that the vibrational modes observed in these spectra are mostly intermolecular character between 4ABA and NF molecules during the cocrystal formation process.…”

Section: Thz Spectral Characterization Of Nf 4aba and Its Correspondmentioning

confidence: 99%

“…These characteristics would significantly impact the therapeutic activity of NF drug. Multi-component crystals or also named cocrystals of NF with various CCFs based on the molecular attributes present have been reported recently [11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

“…Two cocrystals NF-4-aminobenzoic acid and NF-urea come under the category of pharmaceutical cocrystals [12][13][14][15] because of the generally recognized as safe status of the coformers. , and the green shadow shows the intermolecular interaction due to hydrogen-bond effect between NF and 4ABA molecules.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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

Cai

Xue

et al. 2016

Preprint

View full text Add to dashboard Cite

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.

show abstract

Section: Thz Spectral Characterization Of Nf 4aba and Its Correspondmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

Cai

Xue

et al. 2016

Preprint

View full text Add to dashboard Cite

show abstract

“…These are mainly studies of intrinsic dissolution rates measured in simple buffers or in biorelevant media and estimated on the basis of their individual molar extinction coefficients in the respective medium, with the use of simple set ups or compendial apparatus (i.e. USP Apparatus 2) (15)(16)(17)(18).…”

Section: Introductionmentioning

confidence: 99%

Small-Scale Assays for Studying Dissolution of Pharmaceutical Cocrystals for Oral Administration

et al. 2015

View full text Add to dashboard Cite

Abstract. The purpose of this study was to better understand the dissolution properties and precipitation behavior of pharmaceutical cocrystals of poorly soluble drugs for the potential for oral administration based on a small-scale dissolution assay. Carbamazepine and indomethacin cocrystals with saccharin and nicotinamide as coformers were prepared with the sonic slurry method. Dissolution of the poorly soluble drugs indomethacin and carbamazepine and their cocrystals was studied with a small-scale dissolution assay installed on a SiriusT3 instrument. Two methodologies were used: (i) surface dissolution of pressed tablet (3 mm) in 20 mL running for fixed times at four pH stages (pH 1.8, pH 3.9, pH 5.4, pH 7.3) and (ii) powder dissolution (2.6 mg) in 2 mL at a constant pH (pH 2). Improved dissolution and useful insights into precipitation kinetics of poorly soluble compounds from the cocrystal form can be revealed by the smallscale dissolution assay. A clear difference in dissolution/precipitation behaviour can be observed based on the characteristics of the coformer used.

show abstract

“…The cocrystal TMZ:succinic acid (1:1) can even be stable for up to 1 year under laboratory conditions with no sign of discoloration. In other cases, pharmaceutical cocrystals of caffeine [133] and nitrofurantoin [134] can also be engineered to improve the stability to moisture.…”

Section: Crystal Engineering Of Pharmaceutical Cocrystalsmentioning

confidence: 98%

Hydrogen Bonding in Supramolecular Crystal Engineering

Wang

Zheng

2015

Lecture Notes in Chemistry

View full text Add to dashboard Cite

This chapter emphases the important role of hydrogen bonding in crystal engineering for preparing fascinating architectures and engineering desired properties. The relatively high directionality and strength of hydrogen bonds make the prediction and control of molecular orientation in organic solids practical and reliable. Especially, strong hydrogen bonds like O-H···O, O-H···N, and N-H···O interactions are more useful. The introduction of supramolecular synthons and retrosynthesis theory has helped crystal chemists a lot in understanding and designing more complex structures. A large number of crystal structures reported in Cambridge Structure Database (CSD) provided a helpful tool for searching and analyzing specific interaction modes. Up to now, with the development of basic concepts and principles and the wide applications, the subject of crystal engineering has matured. Various intriguing structures and complicated entanglements have been constructed based on hydrogen bonds, such as nanocapsules, nanotubes, and n-Borromean arrayed topologies. The crystal engineering strategy has lent chemists the ability to control solid state reactions regio-and stereo-specifically and improve the physicochemical properties of drugs using pharmaceutical cocrystals. In addition, it will be seen that hydrogen bonding can also be used to prepare robust porous materials for gas adsorption and separation.

show abstract

Nitrofurantoin– p ‐aminobenzoic acid cocrystal: Hydration stability and dissolution rate studies

Cited by 110 publications

References 21 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

Small-Scale Assays for Studying Dissolution of Pharmaceutical Cocrystals for Oral Administration

Hydrogen Bonding in Supramolecular Crystal Engineering

Contact Info

Product

Resources

About