Bromine K-Edge X-Ray Absorption Near-Edge Structure Analysis on Hydrobromide-Salt Crystals and the Solid Dispersion of Active Pharmaceutical Ingredients

Suzuki, Hironori; Tomita, Asumi; Ito, Masataka; Noguchi, Shuji

doi:10.1248/cpb.c21-00912

Cited by 7 publications

(3 citation statements)

References 15 publications

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“…3a), considering the high reproducibility of this method. 9,11,16) Each spectrum had four peaks in this region. The peak heights of forms A and I were comparable, while the heights of the first and second peaks of form II were higher than those of forms A and I.…”

Section: Resultsmentioning

confidence: 99%

Characterization of Ambroxol and Its Hydrochloride Salt Crystals by Bromine K-Edge X-Ray Absorption Near-Edge Structure Spectroscopy and X-Ray Crystal Structure Analysis

Huang,

Suzuki,

Ito

et al. 2023

CHEMICAL & PHARMACEUTICAL BULLETIN

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Polymorphic crystals of ambroxol, forms I and II, and form A ambroxol hydrochloride crystals were characterized with bromine K-edge X-ray absorption near-edge structure (XANES) spectroscopy and singlecrystal X-ray structure analysis. The XANES spectra had unique shapes depending on the crystal forms. Refined single-crystal structures revealed different interatomic interactions around bromine atoms, such as C-H…Br and N-H…Br hydrogen bonds, Br…O halogen bonds, and N-H…π interactions. Differences in these weak interactions could affect the electronic states of the bromines, resulting in differences in the XANES spectra. The results demonstrated that weak non-conventional interatomic interactions could alter the shape of XANES spectra. Hence, the spectra could be used for evaluating polymorphs of active pharmaceutical ingredients.

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Section: Resultsmentioning

confidence: 99%

Characterization of Ambroxol and Its Hydrochloride Salt Crystals by Bromine K-Edge X-Ray Absorption Near-Edge Structure Spectroscopy and X-Ray Crystal Structure Analysis

Huang,

Suzuki,

Ito

et al. 2023

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…XANES spectroscopy is the method with a high element specificity and is suitable for detecting specifically the interatomic interactions at the X-ray absorbing atoms. The typical target elements of XANES spectroscopy in pharmaceutical research are chlorine, [9][10][11] bromine 12,13) and phosphorus, 14) although XANES may be applied, in principle, to all elements.…”

Section: Introductionmentioning

confidence: 99%

C–H▪▪▪S Hydrogen Bonds in Ampicillin and Amoxicillin Crystals Investigated by Sulfur K-Edge X-Ray Absorption Near-Edge Structure Spectroscopy and Single-Crystal X-Ray Structure Analysis

Suzuki

Matsubara

Nakata

et al. 2022

CHEMICAL & PHARMACEUTICAL BULLETIN

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Sulfur K-edge X-ray absorption near-edge structure (XANES) spectroscopy was evaluated for its ability to detect non-conventional C-H▪▪▪S hydrogen bonds in crystals of the sulfur-containing penam antibiotics ampicillin and amoxicillin. The XANES spectra of the nearly isomorphous crystals of ampicillin trihydrate and amoxicillin trihydrate were very similar, whereas that of ampicillin anhydrate displayed unique features. Single-crystal X-ray structure analyses revealed that the C-H▪▪▪S hydrogen bond geometries and the chemical types of the hydrogen donors differed between the isomorphous trihydrate crystals and ampicillin anhydrate crystal. These observations demonstrate that the shapes of the sulfur K-edge XANES spectra are dependent on the nature of the C-H▪▪▪S hydrogen bonds. Sulfur K-edge XANES spectroscopy shows promise for use in the detection and analysis of non-covalent interactions, including hydrogen bonds to sulfur atoms, within active pharmaceutical ingredients.

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“…However, there are only a few studies on the method used for the evaluation of APIs. Two studies have used the XAFS method to investigate the chemical environment of Cl ion in clarithromycin hydrochloride hydrate salt form A and Br ion in eletriptan hydrobromide salt, respectively. , Other studies applied the method to mosapride salt and solvate crystals, indomethacin polymorphs and amorphous solid dispersions (ASDs), and disodium etidronate polymorphs and its amorphous form. − All these studies showed that the shape of the XANES spectrum is changed by the weak noncovalent interatomic interactions such as hydrogen bond and halogen bond. Therefore, this method could be used to discriminate the crystal polymorphs of APIs.…”

Section: Introductionmentioning

confidence: 99%

Analysis of Cimetidine Crystal Polymorphs by X-ray Absorption Near-Edge Spectroscopy

et al. 2022

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Sulfur K-edge X-ray absorption near-edge spectroscopy (XANES) measurements were performed to characterize the crystal polymorphs of the active pharmaceutical ingredients (APIs) containing sulfur atoms. Cimetidine (CIM) was used as a model API. Each crystal form of CIM has its own XANES spectrum, so we can discriminate the crystal form by its spectrum. The analysis of the crystal structure of CIM revealed that the difference in the shape of XANES spectra was ascribable to the difference in the C−S−C bond angle of CIM molecules and the intermolecular hydrogen bonds, such as C−H•••S and N−H•••S, and S−S interaction. It was found that the peak shape of the XANES spectrum is gentle when the C−S−C bond angle is large, while the peak shape can be steep when the C−S−C bond angle is small. Furthermore, it was found that the peak energy values varied depending on the hydrogen bonds and S−S interaction. By linear combination fitting using XANES spectra, it was possible to quantify the ratio of CIM form A crystal in mixed powders of form A and monohydrate crystals. These results indicate that XANES measurements can be a useful technique to evaluate the crystal polymorphism of APIs containing S atom in pharmaceutical formulation.

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Bromine K-Edge X-Ray Absorption Near-Edge Structure Analysis on Hydrobromide-Salt Crystals and the Solid Dispersion of Active Pharmaceutical Ingredients

Cited by 7 publications

References 15 publications

Characterization of Ambroxol and Its Hydrochloride Salt Crystals by Bromine K-Edge X-Ray Absorption Near-Edge Structure Spectroscopy and X-Ray Crystal Structure Analysis

Characterization of Ambroxol and Its Hydrochloride Salt Crystals by Bromine K-Edge X-Ray Absorption Near-Edge Structure Spectroscopy and X-Ray Crystal Structure Analysis

C–H▪▪▪S Hydrogen Bonds in Ampicillin and Amoxicillin Crystals Investigated by Sulfur K-Edge X-Ray Absorption Near-Edge Structure Spectroscopy and Single-Crystal X-Ray Structure Analysis

Analysis of Cimetidine Crystal Polymorphs by X-ray Absorption Near-Edge Spectroscopy

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