A novel class of phenol–pyridine co-crystals for second harmonic generation

Huang, Kin-Shan; Britton, Doyle; Etter, the late Margaret C.; Byrn, Stephen R.

doi:10.1039/a604311j

Cited by 137 publications

(78 citation statements)

References 14 publications

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“…Therefore, it would be fair to summarize co-crystals as being long known but little studied. However, interest in co-crystals is increasing with potential applications in nonlinear optics (NLO), 34 solventfree organic synthesis, 35,36 host-guest chemistry, [37][38][39] and photographic film formulation. The concept of crystal engineering was introduced by Pepinsky 41 in 1955 and implemented by Schmidt in the context of organic solid-state photochemical reactions.…”

Section: Introductionmentioning

confidence: 99%

Pharmaceutical Co-Crystals

Vishweshwar

McMahon

Bis

et al. 2006

Journal of Pharmaceutical Sciences

883

634

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Section: Introductionmentioning

confidence: 99%

Pharmaceutical Co-Crystals

Vishweshwar

McMahon

Bis

et al. 2006

Journal of Pharmaceutical Sciences

883

634

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“…Examples are cocrystals of peptides, 118 cocrystals containing the sunscreen para-aminobenzoic acid, 119 cocrystals containing nucleotide bases, 120 and cocrystals showing promise as nonlinear optical materials. 121 Figure 6. Diagrams from single-crystal structure analyses of aminophylline crystals.…”

Section: Examples Of Cocrystals From the Literaturementioning

confidence: 99%

Diversity in Single- and Multiple-Component Crystals. The Search for and Prevalence of Polymorphs and Cocrystals

Stahly

2007

Crystal Growth & Design

480

342

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A detailed description of polymorph screening procedures is presented. On the basis of the results of 245 polymorph screens, organic compounds were found to exist in multiple solid forms quite frequently. About 90% exhibited multiple crystalline and noncrystalline forms; about 50% exhibited polymorphism. Cocrystals are defined, and cocrystal screening is discussed. Data from 64 cocrystal screens show that cocrystals were found in 61% of the cases, and the total number of cocrystals found was 192.

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“…38 Given that the pK a values of the polymers vary from 5 to 6.0, 24-26,39 the pK a difference between the secondary amine of the drug and carboxylic acid of the polymers falls within the limits of salt formation of ≥ 2-3 in each case. 40 Therefore, these formulations could be considered as amorphous polymeric drug salts. Amorphous drug-polymer salts have also been produced by 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 20 Weuts et al, 41 Song et al 42 and Maniruzzaman et al 43 In each case an ionic interaction between the COOH groups of the polymers and amino groups of the drugs was detected.…”

Section: Solid State Characterization Of Amorphous Solid Dispersionsmentioning

confidence: 99%

Amorphous Polymeric Drug Salts as Ionic Solid Dispersion Forms of Ciprofloxacin

et al. 2017

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Ciprofloxacin (CIP) is a poorly soluble drug that also displays poor permeability. Attempts to improve the solubility of this drug to date have largely focused on the formation of crystalline salts and metal complexes. The aim of this study was to prepare amorphous solid dispersions (ASDs) by ball milling CIP with various polymers. Following examination of their solid state characteristics and physical stability, the solubility advantage of these ASDs was studied, and their permeability was investigated via parallel artificial membrane permeability assay (PAMPA). Finally, the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of the ASDs were compared to those of CIP. It was discovered that acidic polymers, such as Eudragit L100, Eudragit L100C==, Carbopol and HPMCAS, were necessary for the amorphization of CIP. In each case, the positively charged secondary amine of CIP was found to interact with carboxylate groups in the polymers, forming amorphous polymeric drug salts. Although the ASDs began to crystallize within days under accelerated stability conditions, they remained fully XCray amorphous following exposure to 90% RH at 25 oC, and demonstrated higher than predicted glass transition temperatures. The solubility of CIP in water and simulated intestinal fluid was also increased by all of the ASDs studied. Unlike a number of other solubility enhancing formulations, the ASDs did not decrease the permeability of the drug.Similarly, no decrease in antibiotic efficacy was observed, and significant improvements in the MIC and MBC of CIP were obtained with ASDs containing HPMCASC") and HPMCASCMG. Therefore, ASDs may be a viable alternative for formulating CIP with improved solubility, bioavailability and antimicrobial activity.

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A novel class of phenol–pyridine co-crystals for second harmonic generation

Cited by 137 publications

References 14 publications

Pharmaceutical Co-Crystals

Pharmaceutical Co-Crystals

Diversity in Single- and Multiple-Component Crystals. The Search for and Prevalence of Polymorphs and Cocrystals

Amorphous Polymeric Drug Salts as Ionic Solid Dispersion Forms of Ciprofloxacin

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