Correlation between microstructure and bioequivalence in Anti-HIV Drug Efavirenz

Fandaruff, Cinira; Silva, Marcos Antônio Segatto; Bedor, Danilo César Galindo; Santana, Davi Pereira de; Rocha, Helvécio Vinícius Antunes; Rebuffi, Luca; Ricardo, Cristy Leonor Azanza; Scardi, Paolo; Cuffini, Silvia Lucía

doi:10.1016/j.ejpb.2015.01.020

Cited by 22 publications

(16 citation statements)

References 37 publications

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“…Therefore, the LPA capability of determining the characteristics of materials, mostly with 'large' (several hundreds of nanometres) crystalline domains, is strongly affected by the shape and by the stability of the instrumental profile function (IPF). Studies based on such an 'at-the-limits' LPA are given by Malerba et al (2014) and Fandaruff et al (2015). Synchrotron radiation seems the most appropriate choice to collect high-quality diffraction data, thanks to the high beam brilliance, energy selectivity and focusing conditions.…”

Section: The Instrumental Function In Powder Diffractionmentioning

confidence: 99%

Understanding the instrumental profile of synchrotron radiation X-ray powder diffraction beamlines

Rebuffi

Río

Busetto

et al. 2017

J Synchrotron Radiat

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A Monte Carlo algorithm has been developed to calculate the instrumental profile function of a powder diffraction synchrotron beamline. Realistic models of all optical elements are implemented in a ray-tracing software. The proposed approach and the emerging paradigm have been investigated and verified for several existing X-ray powder diffraction beamlines. The results, which can be extended to further facilities, show a new and general way of assessing the contribution of instrumental broadening to synchrotron radiation data, based on ab initio simulations.

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Section: The Instrumental Function In Powder Diffractionmentioning

confidence: 99%

Understanding the instrumental profile of synchrotron radiation X-ray powder diffraction beamlines

Rebuffi

Río

Busetto

et al. 2017

J Synchrotron Radiat

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“…Braga et al achieved a new polymorph of p-methylbenzyl alcohol, which is isomorphous with the crystal of p-chlorobenzyl alcohol, by hetero-seeding with a small quantity of the latter (Romasanta et al, 2017). Although there have been several case studies on isostructurality consisting of single-component forms, only a few examples of multicomponent forms are reported in the literature (Cinčić et al, 2008a;Fandaruff et al, 2015;Clarke et al, 2012;Galcera & Molins, 2009).…”

Section: Introductionmentioning

confidence: 99%

Isomorphism: `molecular similarity to crystal structure similarity' in multicomponent forms of analgesic drugs tolfenamic and mefenamic acid

Ranjan

Devarapalli

Kundu

et al. 2020

IUCrJ

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The non-steroidal anti-inflammatory drugs mefenamic acid (MFA) and tolfenamic acid (TFA) have a close resemblance in their molecular scaffold, whereby a methyl group in MFA is substituted by a chloro group in TFA. The present study demonstrates the isomorphous nature of these compounds in a series of their multicomponent solids. Furthermore, the unique nature of MFA and TFA has been demonstrated while excavating their alternate solid forms in that, by varying the drug (MFA or TFA) to coformer [4-dimethylaminopyridine (DMAP)] stoichiometric ratio, both drugs have produced three different types of multicomponent crystals, viz. salt (1:1; API to coformer ratio), salt hydrate (1:1:1) and cocrystal salt (2:1). Interestingly, as anticipated from the close similarity of TFA and MFA structures, these multicomponent solids have shown an isomorphous relation. A thorough characterization and structural investigation of the new multicomponent forms of MFA and TFA revealed their similarity in terms of space group and structural packing with isomorphic nature among the pairs. Herein, the experimental results are generalized in a broader perspective for predictably identifying any possible new forms of comparable compounds by mapping their crystal structure landscapes. The utility of such an approach is evident from the identification of polymorph VI of TFA from hetero-seeding with isomorphous MFA form I from acetone-methanol (1:1) solution. That aside, a pseudopolymorph of TFA with dimethylformamide (DMF) was obtained, which also has some structural similarity to that of the solvate MFA:DMF. These new isostructural pairs are discussed in the context of solid form screening using structural landscape similarity.

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“…2020, 88, 1 2 of 15 important problem that requires close attention and comprehensive study. As it turns out, various crystal modifications, not only of biologically active substances themselves, but also of excipients, are able to radically change (and not always for the better) the technological, pharmaceutical or pharmacological characteristics of drugs already produced, and, therefore, standardized and thoroughly tested [1][2][3][4][5][6][7]. It is for this reason that in modern conditions polymorphism of pharmaceuticals is taken under strict control by the regulatory authorities in many countries of the world [8].…”

Section: Introductionmentioning

confidence: 99%

Crystal Habits and Biological Properties of N-(4-Trifluoromethylphenyl)-4-Hydroxy-2,2-Dioxo-1H-2λ6,1-Benzothiazine-3-Carboxamide

et al. 2019

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In order to study polymorphic modifications of N-(4-trifluoromethylphenyl)-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamide, which is of interest as a promising analgesic, its three colorless crystal forms with different habitus have been obtained: sticks of ethyl acetate, plates of meta-xylene and blocks of ortho-xylene. However, the X-ray diffraction analysis has shown that all the forms studied have the identical molecular and crystal structure in spite of such significant differences in appearance. Moreover, pharmacological tests have revealed significant differences in the analgesic activity in these samples (a total of five experimental models were used: “acetic-acid-induced writhing”, “hot plate”, “thermal irritation of the tail tip” (tail-flick), “tail electric stimulation” and “neuropathic pain”), acute toxicity and the ability to cause gastric damage. As a result, only the plate crystal form of N-(4-trifluoromethylphenyl)-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamide is recommended for further studies. Thus, it has been proven that the habitus of crystals is an important characteristic of the drug substance and is able to have a noticeable effect on its biological properties. Changes in habitus should be considered as a guide to the mandatory verification of at least the basic pharmacological parameters of the new form regardless of whether the molecular and crystal structure changes.

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Correlation between microstructure and bioequivalence in Anti-HIV Drug Efavirenz

Cited by 22 publications

References 37 publications

Understanding the instrumental profile of synchrotron radiation X-ray powder diffraction beamlines

Understanding the instrumental profile of synchrotron radiation X-ray powder diffraction beamlines

Isomorphism: `molecular similarity to crystal structure similarity' in multicomponent forms of analgesic drugs tolfenamic and mefenamic acid

Crystal Habits and Biological Properties of N-(4-Trifluoromethylphenyl)-4-Hydroxy-2,2-Dioxo-1H-2λ6,1-Benzothiazine-3-Carboxamide

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