Pharmaceutical Salts of Piroxicam and Meloxicam with Organic Counterions

Huang, Shan; Venables, Dean S.; Lawrence, Simon E.

doi:10.1021/acs.cgd.2c00722

Cited by 7 publications

(4 citation statements)

References 103 publications

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“…All other hydrogen atoms were placed in geometrically calculated positions using the riding model, with C–H = 0.93–0.97 Å and N–H = 0.86–0.89 Å, and Uiso (H) (in the range of 1.2–1.5 times Ueq of the parent atom). DIAMOND was used for creating figures, and PLATON was used for the analysis of potential hydrogen bonds and short ring interactions. , Crystallographic parameters are provided in Table .…”

Section: Methodsmentioning

confidence: 99%

“…An average of four scans was taken for each spectrum obtained with a resolution of 4 cm −1 . PXRD data were collected using a STOE STADI MP diffractometer with Cu Kα radiation using a linear position-sensitive detector over the 2θ range of 3.5−45.5°with an increment of 0.05°at a rate of 2°T 32 and PLATON was used for the analysis of potential hydrogen bonds and short ring interactions. 33,34 Crystallographic parameters are provided in Table 1.…”

Section: ■ Introductionmentioning

confidence: 99%

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Exploring the Crystal Structure Landscape of Sulfasalazine through Various Multicomponent Crystals

Huang

Cheemarla

Tiana

et al. 2023

Crystal Growth & Design

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Sulfasalazine is used as an anti-inflammatory drug to treat large intestine diseases and atrophic arthritis. In the solid state, two tautomers are known: an amide tautomer (triclinic polymorph) and an imide tautomer (monoclinic polymorph). Crystallization of six new multicomponent solids of sulfasalazine with three cocrystal formers and three salt formers has been achieved by slurry, liquid-assisted grinding and slow evaporation methods. All of the solid forms are characterized by X-ray diffraction techniques, thermal analysis, and Fourier transform infrared spectroscopy. The crystal structural analysis reveals that two sulfasalazine molecules or anions arrange in a head-to-head fashion involving their pyridyl, amide, and sulfonyl groups in an R 2 2(7):R 2 2(8):R 2 2(7) motif. This is the key structural unit appearing in both sulfasalazine imide polymorph and all six multicomponent crystals. In addition, sulfasalazine exists in the amide form in all unsolvated multicomponent crystals obtained in this work and adopts the imide tautomer in the solvated cocrystals and salt. Hirshfeld surface analysis and the associated two-dimensional (2D) fingerprint plots demonstrate that sulfasalazine has significant hydrogen bond donor capability when cocrystallized and is a significant hydrogen bond acceptor in the salts. The frontier molecular orbital analysis indicates that sulfasalazine cocrystals are chemically more stable than the salts.

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Section: Methodsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Exploring the Crystal Structure Landscape of Sulfasalazine through Various Multicomponent Crystals

Huang

Cheemarla

Tiana

et al. 2023

Crystal Growth & Design

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“…Moving from a moderate to a strong -N-H • • • H-bond implies that the ether oxygen atom from the Pluronic segment has been replaced by a carbonyl or sulfone oxygen from MX. The addition of MX into the PU matrix would lead to the breaking of some intramolecular C-H • • • O and S-O • • • H-C H-bonds in MX [45], and it would build intermolecular links with donor or acceptor groups from the PU matrix, such as C=O • • • O-S and C=O • • • H-N (MX). The other carbonyl bands observed around 1740 cm −1 (ester carbonyl from the lateral chain of the LDI segment and/or free urethane groups) and 1660 cm −1 ("ordered", strongly H-bonded urethane C=O • • • H-N-) have a similar intensity to the native PU.…”

Section: Ftir Spectramentioning

confidence: 99%

Thermosensitive Polyurethane-Based Hydrogels as Potential Vehicles for Meloxicam Delivery

Plugariu,

Gradinaru,

Avadanei

et al. 2023

Pharmaceuticals

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Meloxicam (MX) is a nonsteroidal anti-inflammatory drug (NSAID) used mainly to reduce pain, inflammation, and fever. In the present study, thermosensitive polyurethane (PU)-based hydrogels with various excipients (PEG, PVP, HPC, and essential oil) were prepared and loaded with MX. Rheological investigations were carried out on the PU-based formulations in various shear regimes, and their viscoelastic characteristics were determined. The average size of the PU micelles was 35.8 nm at 37 °C and slightly increased at 37 nm in the presence of MX. The zeta potential values of the hydrogels were between −10 mV and −11.5 mV. At pH = 6 and temperature of 37 °C, the formulated PU-based hydrogels loaded with MX could deliver significant amounts of the active substance, between 60% and 80% over 24–48 h and more than 90% within 2 weeks. It was found that anomalous transport phenomena dominated MX’s release mechanism from the PU-based networks. The results are encouraging for further studies aiming to design alternative carriers to commercial dosage forms of nonsteroidal anti-inflammatory drugs.

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“…cocrystals, salts, hydrates/solvates). , In particular, cocrystals offer many possibilities when it comes to crystal engineering since there are various coformers which can be assembled with target compounds by noncovalent interactions, such as hydrogen-bonding interactions, π–π interactions, halogen bonds, etc . These interactions can manipulate the molecular arrangement in crystal structures, resulting in the modification of the physicochemical properties, such as solubility, luminescence, stability, etc. − …”

Section: Introductionmentioning

confidence: 99%

Experimental and Theoretical Investigation of Hydrogen-Bonding Interactions in Cocrystals of Sulfaguanidine

Huang

Cheemarla

Tiana

et al. 2023

Crystal Growth & Design

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Pharmaceutical cocrystals, a type of multicomponent crystalline material incorporating two or more molecular and/or ionic compounds connected by noncovalent interactions (such as hydrogen bonds, π–π interactions, and halogen bonds), are attracting increasing attention in crystal engineering. Sulfaguanidine (SGD), one of the most frequently used sulfonamide compounds, was chosen as a model compound in this work to further investigate the hydrogen bond interactions in cocrystals, since it possesses various hydrogen bond donor and acceptor sites. Five cocrystals of SGD, synthesized successfully by slurry and slow evaporation methods, were fully characterized by thermal analysis, X-ray techniques, and Fourier transform infrared spectroscopy. To gain insight into the nature of hydrogen-bonding interactions, theoretical calculations including the analysis of Hirshfeld surface, MEPS (molecular electrostatic potential surface), and QTAIM (quantum theory of atoms in molecules) were conducted. The results are a part of a systematic study of cocrystals of sulfonamides that aims to establish synthon hierarchies in cocrystals containing molecules with multiple hydrogen-bonding functional groups.

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Pharmaceutical Salts of Piroxicam and Meloxicam with Organic Counterions

Cited by 7 publications

References 103 publications

Exploring the Crystal Structure Landscape of Sulfasalazine through Various Multicomponent Crystals

Exploring the Crystal Structure Landscape of Sulfasalazine through Various Multicomponent Crystals

Thermosensitive Polyurethane-Based Hydrogels as Potential Vehicles for Meloxicam Delivery

Experimental and Theoretical Investigation of Hydrogen-Bonding Interactions in Cocrystals of Sulfaguanidine

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