A comprehensive approach toward concomitant triclabendazole polymorphism in pharmaceutical products

Salazar-Rojas, Duvernis; Kaufman, Teodoro S.; Maggio, Rubén M.

doi:10.1016/j.jddst.2021.102386

Cited by 5 publications

(5 citation statements)

References 34 publications

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“…In order to execute the regression, the solvents’ densities are taken from ref ; and the melting enthalpy (Δ fus H = 36.69 kJ mol –1 ) and the melting temperature ( T m = 450.45 K) of triclabendazole are acquired from ref . The parameters’ values of A , B , and C in the semi-empirical Apelblat equation, λ and h in the semi-empirical λ h equation, and a ij and b ij in the Wilson and NRTL models are organized in Tables and , together with the RAD and rmsd magnitude.…”

Section: Resultsmentioning

confidence: 99%

“…By careful analysis of the IR spectra obtained, one can observe that the solids equilibrated with various neat solvents present identical characteristic absorption peaks as the raw material of triclabendazole as well as those presented in the previous documents. 38,39 As a result, no appearance of solvation or polymorph transformation took place for the solute of triclabendazole in all the experimental processes. A careful comparison of the IR absorption spectra determined in this work with that reported by Salazar-Rojas 38 and Tothadi, 39 the raw material of triclabendazole used in this research belongs to form (I).…”

mentioning

confidence: 95%

“…38,39 As a result, no appearance of solvation or polymorph transformation took place for the solute of triclabendazole in all the experimental processes. A careful comparison of the IR absorption spectra determined in this work with that reported by Salazar-Rojas 38 and Tothadi, 39 the raw material of triclabendazole used in this research belongs to form (I).…”

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confidence: 95%

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Solubility and Mixing Thermodynamic Properties of Triclabendazole in 14 Neat Solvents at Elevated Temperatures from 278.15 to 318.15 K

Chen

Zhu

et al. 2021

J. Chem. Eng. Data

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The triclabendazole solubility in 14 pure solvents including methanol, 1,2-dichloroethane (1,2-DCE), ethanol, n-butyl acetate, n-propanol, ethyl formate, isopropanol, n-butanol, isobutanol, ethyl acetate, acetonitrile, ethylene glycol (EG), n-propyl acetate, and n-pentyl acetate was experimentally obtained in the current research by means of the shake-flask equilibration technique at elevated temperatures from 278.15 to 318.15 K and pressure p = 101.2 kPa. With increasing temperatures, the values of the mole fraction solubility of drug triclabendazole presented a monotonic increase in tendency, and the following decreasing trend in the 14 solvents: (n-butanol, n-pentyl acetate) > n-butyl acetate > n-propyl acetate > ethyl acetate > n-propanol > ethanol > ethyl formate > isobutanol > methanol > isopropanol > 1,2-DCE > acetonitrile > EG. Two semi-empirical equations (Apelblat equation and λh equation) and two activity coefficient models (Wilson model and NRTL model) were utilized to associate the determined solubility data. The obtained maximum root-mean-square deviation and relative average deviation were, respectively, 2.31 × 10–4 and 1.41 × 10–2. In general, the Apelblat equation presented lower deviations compared with the other relationships for a specific pure solvent. Also, the mixing thermodynamic functions, reduced excess enthalpy, and infinite dilution activity coefficient were obtained from the Wilson model.

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 95%

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Solubility and Mixing Thermodynamic Properties of Triclabendazole in 14 Neat Solvents at Elevated Temperatures from 278.15 to 318.15 K

Chen

Zhu

et al. 2021

J. Chem. Eng. Data

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“…This combinatorial technique is particularly popular among traditional medicine manufacturers [52,56,[58][59][60][61]. Not only to ensure the compositions among the formulations remain the same, a combination of spectroscopy and chemometric could be used to differentiate polymorphism in drugs such as triclabendazole [62]. HPLC, GC-MS, XPRD, 1 H NMR, NIR PCA, HCA Omeprazole Discrimination of omeprazole and omeprazole magnesium based on manufacturing source AMSQFM, average method of systematic quantified fingerprint method; ATR-FTIR, attenuated total reflection fourier transformed infrared; BP-NN, back propagation neural network; CCA, canonical correlation analysis; DR, decision tree; FTIR, Fourier transform-infrared; FT-NIR, Fourier transform nearinfrared; GC-MS, gas chromatography-mass spectrometry; HCA, hierarchical cluster analysis; HPLC, highperformance liquid chromatography; HPLC-UV-ELSD; high-performance liquid chromatographyultraviolet detector-evaporative light scattering detector; KNN, K-nearest neighbor; LDA, linear discriminant analysis; MIR, mid-infrared; NIR, near-infrared; QAMS, quantitative analysis of multicomponents by single marker; QC, quality control; UHPLC-Q-Exactive Orbitrap/MS, ultraperformance liquid chromatography Quadrupole-Exactive Orbitrap tandem mass spectrometry; XPRD, X-ray powder diffractometry…”

Section: Quality Control Of Drug Manufacturingmentioning

confidence: 99%

Chemometric-empowered spectroscopic techniques in pharmaceutical fields: A bibliometric analysis and updated review

Zulkifli,

Fakri,

Odigie

et al. 2023

Narra X

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Undeniable increase in pharmaceutical demand has encouraged researchers to develop analytical techniques to analyze drugs and monitor their effects. Chemometrics enabled simple spectroscopic approaches (such as infrared or UV spectroscopy) to analyze complex samples, including drug formulations, excreted fluids and tissues of living organisms. The aim of this study was to evaluate the research trend of this combinatorial technique utilized for pharmaceutical-related sample analysis using a bibliometric analysis. Bibliometric data of published literature from the Scopus database on March 14, 2023 were retrieved using the keyword combinations of "multivariate", "chemometrics", "pattern recognition", "drug", "pharmaceutical" and "spectroscopy". Network visualization analysis was performed using VOSviewer on the co-occurring keywords and authorships, presenting data such as top cited papers (n=10). The literature review was performed based on the research trend revealed by the clusters that emerged in the network visualization. The analysis revealed that the first paper was published in 1973 (n=1) and a total of 3544 records have been published as of March 14, 2023, comprising original research articles (n=3144, 88.71%) and review articles (n=232, 6.55%). The keyword “chemometrics” with Total Link Strength (TLS) of 826 emerged as the most abundant, followed by “metabolomics” (TLS=388), “Raman spectroscopy” (TLS=280), “metabonomics” (TLS=272), “nuclear magnetic resonance” or “NMR” (TLS=271), and “multivariate analysis” (TLS=254). Network visualization revealed that the research falls into two general categories: (1) drug toxicity and efficacy monitoring and (2) quality control of drug manufacturing. The top cited paper (n=3269) was a review article published in 1999 describing the utility of nuclear magnetic resonance combined with multivariate statistics for metabolite profiling of biological samples. The chemometric-empowered spectroscopy techniques were expected to provide objective measurement during clinical studies and monitoring of therapeutic effects.

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“…The polymorphic phenomenon is well known for organic compounds [ 1 , 2 , 3 , 4 ]. It is of particular interest to the pharmaceutical industry, since polymorphs might differ in solubility, dissolution rate, bioavailability, stability, hardness, melting point, etc.…”

Section: Introductionmentioning

confidence: 99%

Polymorphism of Butyl Ester of Oleanolic Acid—The Dominance of Dispersive Interactions over Electrostatic

Langer

Wicher

Dutkiewicz

et al. 2023

IJMS

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Oleanolic (OA) and glycyrrhetinic acids (GE), as well as their derivatives, show a variety of pharmacological properties. Their crystal structures provide valuable information related to the assembly modes of these biologically active compounds. In the known-to-date crystals of OA esters, their 11-oxo derivatives, and GE ester crystals, triterpenes associate, forming different types of ribbons and layers whose construction is based mainly on van der Waals forces and weak C-H···O interactions. New crystal structures of 11-oxo OA methyl ester and the polymorph of OA butyl ester reveal an alternative aggregation mode. Supramolecular architectures consist of helical chains which are stabilized by hydrogen bonds of O-H···O type. It was found that two polymorphic forms of butyl OA ester (layered and helical) are related monotropically. In a structure of metastable form, O-H···O hydrogen bonds occur, while the thermodynamically preferred phase is governed mainly by van der Waals interactions. The intermolecular interaction energies calculated using CrystalExplorer, PIXEL, and Psi4 programs showed that even in motifs formed through O-H···O hydrogen bonds, the dispersive forces have a significant impact.

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A comprehensive approach toward concomitant triclabendazole polymorphism in pharmaceutical products

Cited by 5 publications

References 34 publications

Solubility and Mixing Thermodynamic Properties of Triclabendazole in 14 Neat Solvents at Elevated Temperatures from 278.15 to 318.15 K

Solubility and Mixing Thermodynamic Properties of Triclabendazole in 14 Neat Solvents at Elevated Temperatures from 278.15 to 318.15 K

Chemometric-empowered spectroscopic techniques in pharmaceutical fields: A bibliometric analysis and updated review

Polymorphism of Butyl Ester of Oleanolic Acid—The Dominance of Dispersive Interactions over Electrostatic

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