Solid-state Acetylation of Codeine Phosphate by Aspirin

Galante, Robert N.; Visalli, Anthony J.; Patel, Dahyabhai M.

doi:10.1002/jps.2600681208

Cited by 17 publications

(6 citation statements)

References 18 publications

(2 reference statements)

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“…The latter possibility, in fact, amounts to the prediction of reactivity of molecular crystals. Reactions in the solid state also have implications for the stability of APIs and drug formulations . The present manuscript describes the correlation of the acyl transfer reactivity with crystal structure and inherent noncovalent interactions of several molecular crystals.…”

Section: Introductionmentioning

confidence: 99%

Correlation of Intermolecular Acyl Transfer Reactivity with Noncovalent Lattice Interactions in Molecular Crystals: Toward Prediction of Reactivity of Organic Molecules in the Solid State

Shashidhar

2018

J. Org. Chem.

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Intermolecular acyl transfer reactivity in several molecular crystals was studied, and the outcome of the reactivity was analyzed in the light of structural information obtained from the crystals of the reactants. Minor changes in the molecular structure resulted in significant variations in the noncovalent interactions and packing of molecules in the crystal lattice, which drastically affected the facility of the intermolecular acyl transfer reactivity in these crystals. Analysis of the reactivity vs crystal structure data revealed dependence of the reactivity on electrophile···nucleophile interactions and C-H···π interactions between the reacting molecules. The presence of these noncovalent interactions augmented the acyl transfer reactivity, while their absence hindered the reactivity of the molecules in the crystal. The validity of these correlations allows the prediction of intermolecular acyl transfer reactivity in crystals and co-crystals of unknown reactivity. This crystal structure-reactivity correlation parallels the molecular structure-reactivity correlation in solution-state reactions, widely accepted as organic functional group transformations, and sets the stage for the development of a similar approach for reactions in the solid state.

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Section: Introductionmentioning

confidence: 99%

Correlation of Intermolecular Acyl Transfer Reactivity with Noncovalent Lattice Interactions in Molecular Crystals: Toward Prediction of Reactivity of Organic Molecules in the Solid State

Shashidhar

2018

J. Org. Chem.

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“…1 Solid-solid reactions, although uncommon, may have a profound influence on the performance of the finished dosage form. 2 Kinetic studies of solid-solid reactions will not only aid in developing a fundamental understanding of these reactions, but may ultimately permit the prediction of the performance of formulations. Therefore, development of analytical methods that can be used to monitor solid-solid reaction kinetics will be of great practical utility.…”

Section: Introductionmentioning

confidence: 99%

A Novel X-ray Powder Diffractometric Method for Studying the Reaction between Pseudoephedrine Enantiomers

Duddu

Khin-Khin

Grant

et al. 1997

Journal of Pharmaceutical Sciences

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The opposite enantiomers of pseudoephedrine were observed to react in the solid state to form the racemic compound. A novel powder X-ray diffractometric method was developed for studying the kinetics and mechanism of this reaction. The powder X-ray diffraction patterns of the enantiomers were identical, but the racemic compound exhibited a different pattern because of its different crystal structure. The powder patterns of the enantiomers and the racemic compound revealed that the 4.62 and 4.25 A lines were unique to the enantiomers and the racemic compound, respectively. Teflon holders were filled with equimolar mixtures of the two enantiomers, and the integrated intensities of the 4.62 and 4.25 A lines were measured at 30-min intervals over a period of 8 h. Thus, the disappearance of the crystalline enantiomers and the appearance of the crystalline racemic compound were quantified simultaneously. The rate of disappearance of the crystalline enantiomers followed a diffusion-controlled reaction model originally proposed by Jander in 1927. During the kinetic experiment, the sum of the weight fractions of the enantiomers and the racemic compound progressively decreased from an initial value of unity suggesting the existence of an intermediate noncrystalline phase. The presence of the noncrystalline phase was confirmed by a steady increase in the background of the X-ray patterns. Thus, the unique ability of the X-ray method to quantify only the crystalline phases has demonstrated the existence of a non-crystalline amorphous intermediate in this solid-solid reaction.

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“…The solid-state acetylation of codeine phosphate [28,29], phenylephrine hydrochloride [30], acetaminophen [31] and homatropine [32] by aspirin have been reported. Codeine phosphate in the solid state has also been reported to be esterified by the acid component (citric or tartaric acid) in an effervescent tablet formulation [33].…”

Section: Resultsmentioning

confidence: 98%

Degradation of vitamin D3 in a stressed formulation: The identification of esters of vitamin D3 formed by a transesterification with triglycerides

Ballard

Zhu

Nelson

et al. 2007

Journal of Pharmaceutical and Biomedical Analysis

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Solid-state Acetylation of Codeine Phosphate by Aspirin

Cited by 17 publications

References 18 publications

Correlation of Intermolecular Acyl Transfer Reactivity with Noncovalent Lattice Interactions in Molecular Crystals: Toward Prediction of Reactivity of Organic Molecules in the Solid State

Correlation of Intermolecular Acyl Transfer Reactivity with Noncovalent Lattice Interactions in Molecular Crystals: Toward Prediction of Reactivity of Organic Molecules in the Solid State

A Novel X-ray Powder Diffractometric Method for Studying the Reaction between Pseudoephedrine Enantiomers

Degradation of vitamin D3 in a stressed formulation: The identification of esters of vitamin D3 formed by a transesterification with triglycerides

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