Relationships between crystal structures and thermodynamic properties of phenylbutazone solvates

Hosokawa, Toshihito; Datta, Sharmistha; Sheth, Agam R.; Grant, David J.W.

doi:10.1039/b405547k

Cited by 8 publications

(7 citation statements)

References 13 publications

(13 reference statements)

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“…So, for the nucleation process to take place the shell needs to be removed. The higher the absolute enthalpy value, the more energy is required, 21 what supports the hindrance of the nucleation process. This explains the results obtained in the MZW experiments, where (S)-MA in (S)-ethyl lactate and (R)-MA in (2R,3R)-diethyl tartrate crystallized first.…”

Section: Resultsmentioning

confidence: 98%

Potential of Chiral Solvents for Enantioselective Crystallization. 2. Evaluation of Kinetic Effects

Tulashie

Lorenz

Seidel‐Morgenstern

2009

Crystal Growth & Design

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In part 1 of this work, the potential of chiral solvents in enantioseparation was studied for two pharmaceutical substances with regard to thermodynamics (Cryst. Growth Des. 2008, 8, 3408−3414). Unfortunately, no measurable chiral recognition in terms of the solubility equilibria was observed between the chiral solvents and the chiral systems investigated. In this part 2, studies are directed toward the potential of chiral solvents in enantioseparation based on differences in crystallization kinetics. For the case study performed, mandelic acid as a racemic compound forming system has been chosen. The crystallization kinetics (metastable zone width data with regard to primary nucleation) determined for mandelic acid in the chiral solvents (S)-ethyl lactate and (2R,3R)-diethyl tartrate are shown and discussed. On that basis successful preferential nucleation/crystallization experiments allowed for racemate resolution. To explain the observed results solvation enthalpy data obtained from dissolution enthalpy measurements are considered. Copyright © 2009 American Chemical Society [accessed March 17, 2009

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Section: Resultsmentioning

confidence: 98%

Potential of Chiral Solvents for Enantioselective Crystallization. 2. Evaluation of Kinetic Effects

Tulashie

Lorenz

Seidel‐Morgenstern

2009

Crystal Growth & Design

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“…Phenylbutazone is a potent anti-rheumatic drug that exists in different polymorphic [110][111][112] and solvated forms [113]. Different solubilities, dissolution rates and oral absorption were highlighted between two different polymorphic forms [114].…”

Section: Phenylbutazonementioning

confidence: 99%

“…Phenylbutazone is a potent anti-rheumatic drug existing in different polymorphic and solvated forms [110][111][112][113].…”

Section: Phanylbutazonementioning

confidence: 99%

Polymorph Impact on the Bioavailability and Stability of Poorly Soluble Drugs

2015

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Drugs with low water solubility are predisposed to poor and variable oral bioavailability and, therefore, to variability in clinical response, that might be overcome through an appropriate formulation of the drug. Polymorphs (anhydrous and solvate/hydrate forms) may resolve these bioavailability problems, but they can be a challenge to ensure physicochemical stability for the entire shelf life of the drug product. Since clinical failures of polymorph drugs have not been uncommon, and some of them have been entirely unexpected, the Food and Drug Administration (FDA) and the International Conference on Harmonization (ICH) has required preliminary and exhaustive screening studies to identify and characterize all the polymorph crystal forms for each drug. In the past, the polymorphism of many drugs was detected fortuitously or through manual time consuming methods; today, drug crystal engineering, in particular, combinatorial chemistry and high-throughput screening, makes it possible to easily and exhaustively identify stable polymorphic and/or hydrate/dehydrate forms of poorly soluble drugs, in order to overcome bioavailability related problems or clinical failures. This review describes the concepts involved, provides examples of drugs characterized by poor solubility for which polymorphism has proven important, outlines the state-of-the-art technologies and discusses the pertinent regulations.

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“…The weak C solvent −H···O salen interactions are favored in 2a / 2b , 3 , and 6 because of the effective positive charge of the H atom, which results from partial electron withdrawal from C solvent to electronegative atoms such as Cl ( 2a / 2b , 3 ) or O ( 6 ). The solvent···salen interactions (and also solvent···solvent interactions for 3 , 5 , and 6 ) may lower sufficiently the enthalpy for the solvated system so that the term ( G solute + G solvent ) outweighs the term ( G solvate ), which results in a negative value for Δ G (solvate formation) . , The solvent···salen interactions might also be favored in solution because the salen···salen interactions are weak. Recrystallization from ethanol or ethyl acetate failed thus far to produce any solvated structures.…”

Section: Resultsmentioning

confidence: 99%

“…37 In ESALCT and NPOSAC, the strongest interactions are always found between the organic and Cu(salen) and 6) may lower sufficiently the enthalpy for the solvated system so that the term (G solute + G solvent ) outweighs the term (G solvate ), which results in a negative value for ∆G (solvate formation) . 39,40 The solvent • • • salen interactions might also be favored in solution because the salen • • • salen interactions are weak. Recrystallization from ethanol or ethyl acetate failed thus far to produce any solvated structures.…”

Section: Ni(salen) Conformationsmentioning

confidence: 99%

Ni(salen): a System That Forms Many Solvates with Interacting Ni Atoms

Siegler

Lutz

2008

Crystal Growth & Design

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Recrystallization of [N,N’-Ethylene-bis(salicylideneiminato)]-nickel(II) [Ni(salen)] has been carried out from a large selection of solvents. Crystals can be either solvent free or solvates. This study is based on X-ray crystal structure determinations, which include the redetermination of Ni(salen) at low-temperature, the finding of three new solvates of Ni(salen), that is, Ni(salen)·CH2Cl2, Ni(salen)·AcOH, and Ni(salen)·1.5MeOH, and the reexamination of the known solvate Ni(salen)·chloroform at low- and room-temperature. The crystal structures of Ni(salen) and its solvates are stabilized by salen···salen and/or solvent···salen and/or solvent···solvent intermolecular interactions. A special case is the crystal structure of Ni(salen)·1.5MeOH where the salen/solvent ratio is 2:3 rather than 1:1. For all solvated structures, the solvent and Ni(salen) molecules always interact via Dsolvent−H···Osalen (Dsolvent = C, O) hydrogen bond interactions, the strengths of which depend on the solvent of recrystallization. All structures are characterized by weak Ni−Ni interactions, which are found either in centrosymmetric dimeric units or along one-dimensional chains. Such interactions are favored because of the d8 electronic configuration of Ni(II) and the pseudoplanar geometry of Ni(salen).

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Relationships between crystal structures and thermodynamic properties of phenylbutazone solvates

Cited by 8 publications

References 13 publications

Potential of Chiral Solvents for Enantioselective Crystallization. 2. Evaluation of Kinetic Effects

Potential of Chiral Solvents for Enantioselective Crystallization. 2. Evaluation of Kinetic Effects

Polymorph Impact on the Bioavailability and Stability of Poorly Soluble Drugs

Ni(salen): a System That Forms Many Solvates with Interacting Ni Atoms

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