Direct detection of the crystal form of an active pharmaceutical ingredient in tablets by X-ray absorption fine structure spectroscopy

Huang, Zhenni; Suzuki, Hironori; Ito, Masataka; Noguchi, Shuji

doi:10.1016/j.ijpharm.2022.122057

Cited by 12 publications

(12 citation statements)

References 39 publications

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“…Radiation damages were presumed to be negligible, because the coloring of the samples after the measurements were unrecognizable by the visual inspection and because the damages of the APIs at this synchrotron facility were shown to be little by the facts that the repeated measurements on same samples gave same XANES spectra. 10,13,14) ATHENA 16) was used to process the XANES spectra; the background was subtracted and the spectra were normalized so that the sharp increase at the edge was 1.…”

Section: Methodsmentioning

confidence: 99%

“…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%

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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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Section: Methodsmentioning

confidence: 99%

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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“…If at least one of the coformers is an active pharmaceutical ingredients (APIs) and the other is pharmaceutically acceptable in cocrystals, then it is recognized as a pharmaceutical cocrystal. [4][5][6] Pharmaceutical cocrystals have taken the limelight of interest because they can improve the physicochemical properties of APIs such as solubility, stability, bioavailability without changing the chemical integrity of the drugs. [7,8] Studies have been reported improvements in dissolution rate by Rodríguez-Hornedo et al [9], stability by Liu et al [10] and bioavailability by Nangia et al [11] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structure characterization of three pharmaceutical compounds based on tinidazole compounds

Chen

Zhang

et al. 2023

Preprint

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Tinidazole (TNZ), a 5-nitroimidazole derivative, has received increasing attention due to its pharmacological activities in treatment for amebic and parasitic infections. However, this pharmaceutical shows poor stability. In order to improve the stability of TNZ, we synthesized three novel drug supramolecular compounds successfully. The three compounds discussed in our work were constructed by TNZ and 2,6-dihydroxybenzoic acid (2,6-DHBA), 4-methylsalicylic acid (4-MAC) and 5-chloro-2-hydroxybenzoic acid (5-C-2-HBA). The N-H···O, O-H···O hydrogen bonds and weak C-H···O hydrogen bonds are the primary intermolecular force in the construction of the three compounds. Crystal structure analysis revealed that all the cocrystals exhibit three-dimensional supramolecular architectures. Furthermore, six primary synthons Ⅰ R22 (8), Ⅱ R21 (6), Ⅲ R22(12), Ⅳ R33(9), Ⅴ R22(12), Ⅵ R33(9) forming through various hydrogen bonds are founded in the three compounds. What’s more, resulting pharmaceutical supramolecular compounds showed improved stability. Single-crystal X-ray diffraction analysis, infrared spectroscopy (IR) and thermogravimetric analysis (TGA) are reported.

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“…16 Recently, we have shown that XAFS spectroscopy can be used to discriminate crystal polymorphs of bromhexine hydrochloride and also identified the polymorphs in tablets nondestructively. 18 The additives in the tablets have little influence on the shapes of XAFS spectra. This means that the method can be applied to determine the crystalline form of APIs in actual pharmaceutical formulations containing additive.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Furthermore, in the case of indomethacin ASDs, the crystallization tendency of the API in the ASD had been quantitatively assessed . Recently, we have shown that XAFS spectroscopy can be used to discriminate crystal polymorphs of bromhexine hydrochloride and also identified the polymorphs in tablets nondestructively . The additives in the tablets have little influence on the shapes of XAFS spectra.…”

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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Direct detection of the crystal form of an active pharmaceutical ingredient in tablets by X-ray absorption fine structure spectroscopy

Cited by 12 publications

References 39 publications

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

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

Synthesis and structure characterization of three pharmaceutical compounds based on tinidazole compounds

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

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