Hydrates and Solid-State Reactivity: A Survey of β-Lactam Antibiotics

Hickey, Magali B.; Peterson, Matthew L.; Manas, Eric S.; Álvarez, Juan Carlos; Hæffner, Fredrik; Almarsson, Ӧrn

doi:10.1002/jps.20919

Cited by 41 publications

(23 citation statements)

References 39 publications

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“…31 Analysis of the Gibbs free energy (DG) at 100 C, at both ambient and at 75% relative humidity, has shown amoxicillin trihydrate to be more stable than the anhydrous form under high temperature and humidity conditions. 32 As expected, the anhydrous form is more stable when it is stored under dry conditions. 32 Amoxicillin trihydrate, which is the form used in solid oral formulations, has a single crystal structure and does not exhibit polymorphism.…”

Section: Hydrates and Polymorphismsupporting

confidence: 66%

Biowaiver Monograph for Immediate-Release Solid Oral Dosage Forms: Amoxicillin Trihydrate

Thambavita

Galappatthy

Mannapperuma

et al. 2017

Journal of Pharmaceutical Sciences

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Literature and experimental data relevant to waiver of in vivo bioequivalence (BE) testing for the approval of immediate-release solid oral dosage forms containing amoxicillin trihydrate are reviewed. Solubility and permeability characteristics according to the Biopharmaceutics Classification System (BCS), therapeutic uses, therapeutic index, excipient interactions, as well as dissolution and BE and bioavailability studies were taken into consideration. Solubility and permeability studies indicate that amoxicillin doses up to 875 mg belong to BCS class I, whereas 1000 mg belongs to BCS class II and doses of more than 1000 mg belong to BCS class IV. Considering all aspects, the biowaiver procedure can be recommended for solid oral products of amoxicillin trihydrate immediate-release preparations containing amoxicillin as the single active pharmaceutical ingredient at dose strengths of 875 mg or less, provided (a) only the excipients listed in this monograph are used, and only in their usual amounts, (b) the biowaiver study is performed according to the World Health Organization-, U.S. Food and Drug Administration-, or European Medicines Agency-recommended method using the innovator as the comparator, and (c) results comply with criteria for "very rapidly dissolving" or "similarly rapidly dissolving." Products containing other excipients and those containing more than 875 mg amoxicillin per unit should be subjected to an in vivo BE study.

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Section: Hydrates and Polymorphismsupporting

confidence: 66%

Biowaiver Monograph for Immediate-Release Solid Oral Dosage Forms: Amoxicillin Trihydrate

Thambavita

Galappatthy

Mannapperuma

et al. 2017

Journal of Pharmaceutical Sciences

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“…Solvent interactions can be critical to the quality and performance of the final product,2,3,4 whether it be through controlling the polymorphic form, formation of solvates, or desolvation. The deliberate formation of solvates can offer significant advantages, such as formation of a highly crystalline drug substance with improved physical and chemical stability as compared with nonsolvated forms 5. The cosolvent of marketed products is normally water and the materials are often stoichiometric hydrates.…”

Section: Introductionmentioning

confidence: 99%

A Multi-Technique Approach to the Study of Structural Stability and Desolvation of Two Unusual Channel Hydrate Solvates of Finasteride

Byard

Abraham

Boulton

et al. 2012

Journal of Pharmaceutical Sciences

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“…Since water is nature's solvent, non-toxic and widespread, the scientific community is interested in understanding water assembles in liquids and solids. In particular, medium-sized and large water clusters are important for biology, since they act as surrounding and solvating solutes for biologically active molecules, fill discrete voids and channels in molecular and supramolecular assemblies including their reactive sites and interpenetrate into the interfacial region of hydrophobic surfaces [270][271][272][273]. Besides, water associates are involved in dynamic processes such as proton transport, material or molecular folding, de/resolvation, and others [274,275], and even affect mechanical properties of single crystals [276].…”

Section: Hydrate/solvate Analysermentioning

confidence: 99%

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Вологжанина

2019

Crystals

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Intermolecular interactions of organic, inorganic, and organometallic compounds are the key to many composition-structure and structure-property networks. In this review, some of these relations and the tools developed by the Cambridge Crystallographic Data Center (CCDC) to analyze them and design solid forms with desired properties are described. The potential of studies supported by the Cambridge Structural Database (CSD)-Materials tools for investigation of dynamic processes in crystals, for analysis of biologically active, high energy, optical, (electro)conductive, and other functional crystalline materials, and for the prediction of novel solid forms (polymorphs, co-crystals, solvates) are discussed. Besides, some unusual applications, the potential for further development and limitations of the CCDC software are reported. Crystals 2019, 9, 478 2 of 40 these fields, the manuscript cites only (i) recent works devoted to the analysis of correlations between intermolecular interactions and properties of a small molecule (for example its inclination to form polymorphs, solvates, and co-crystals), or a corresponding solid (from a well-known requirement for non-linear optical materials to crystallize in acentric space groups, to recent studies devoted to the effect of solvent presence on mechanical properties), and (ii) the corresponding software developed to investigate these correlations and to design novel solid forms with desired physicochemical properties. As the description of structure-property networks describes mainly the papers published in the last 10 years in the field of organic, organometallic, and coordination crystals, then the software under discussion will be limited with those developed by the Cambridge Crystallographic Data Centre (CCDC) for material chemistry and crystallography. Various examples of applications of the CCDC software to functional materials including their combination with other software, and restrictions found, will be given.First, the Cambridge Structural Database (CSD) and components of the CSD-Enterprise will be described in Section 2. Then, some properties related to the appearance of a given supramolecular associate, and the tools to search for an associate in the CSD will be reported in Section 3. The properties of solids dependent on the crystal morphology, the Bravais, Friedel, Donnay, and Harker (BFDH) tool for crystal morphology prediction and its' application to affect crystal morphology, polymorphism, and solvatomorphism will be reported in Section 4. Knowledge-based predictions of H-bonded polymorphism, co-crystal formation, mapping of likely intermolecular interactions, and conformer generation for the synthesis of novel functional materials will be discussed in Section 5, and the analysis of local connectivity and whole architectures of solvent molecules in Section 6. Finally, Section 7 contains information about Python API algorithms compatible with the CSD-Enterprise and about some examples of the successful combination of the CSD-Enterprise tools with exte...

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Hydrates and Solid-State Reactivity: A Survey of β-Lactam Antibiotics

Cited by 41 publications

References 39 publications

Biowaiver Monograph for Immediate-Release Solid Oral Dosage Forms: Amoxicillin Trihydrate

Biowaiver Monograph for Immediate-Release Solid Oral Dosage Forms: Amoxicillin Trihydrate

A Multi-Technique Approach to the Study of Structural Stability and Desolvation of Two Unusual Channel Hydrate Solvates of Finasteride

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

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