Investigations on the polymorphism and pseudopolymorphism of triamcinolone diacetate

Suitchmezian, Viktor; Jeß, Inke; Näther, Christian

doi:10.1016/j.ijpharm.2006.05.055

Cited by 20 publications

(26 citation statements)

References 16 publications

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“…In view of the importance of polymorphism we have started systematic investigations on the polymorphism of glucocorticoids 6–8. In recent investigations our interests focus on hydrocortisone (Scheme ), which is one of the most effective antiphlogistic and immune‐suppressive drugs and exhibits extremely high anti‐inflammatory properties.…”

Section: Introductionmentioning

confidence: 99%

Structural, Thermodynamic, and Kinetic Aspectsof the Trimorphism of Hydrocortisone

Suitchmezian

Jeß

Näther

2008

Journal of Pharmaceutical Sciences

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Section: Introductionmentioning

confidence: 99%

Structural, Thermodynamic, and Kinetic Aspectsof the Trimorphism of Hydrocortisone

Suitchmezian

Jeß

Näther

2008

Journal of Pharmaceutical Sciences

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“…3). It must be noted, that this structure is very similar to that of the solvates from triamcinolone diacetate, in which different molecules like alcohols or ketones are embedded 19 . All of these solvates are isotypic crystallizing in space group P2 1 2 1 2 1 and exhibit similar cell parameters like the methanol solvate of clobetasone butyrate.…”

Section: Single Crystal Structuresmentioning

confidence: 59%

“…Finally it must be guaranteed that the process provides only the form preferred by the manufacturer. This was one of our starting points for our investigations on glucocorticoids, in which we have discovered a large number of new forms, that were structurally characterized and investigated for their thermodynamic properties and transition behaviour [19][20][21][22][23][24][25] . In this contribution, we report on our investigations on clobetasone butyrate (Chart 1), which is frequently used in combination with clobetasone for the treatment of skin diseases, allergies and asthma [26][27][28] .…”

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confidence: 99%

Investigations on the polymorphism and pseudopolymorphism of clobetasone butyrate

Näther

Jeß

2011

Collect. Czech. Chem. Commun.

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Clobetasone butyrate was investigated for polymorphism and pseudopolymorphism. Solvent mediated conversion experiments reveal that the commercially available form I represent the thermodynamically most stable form at room temperature and DSC measurements shows that it should also be the most stable form until melting. Form I crystallizes in space group P2 1 2 1 2 1 with three crystallographically independent molecules of similar conformation. From methanol an additional pseudo polymorphic form was discovered. In the crystal structure (space group P2 1 2 1 2 1 ) the solvent molecules are connected to the clobetasone butyrate molecules by O-H···O hydrogen bonding. Investigations of the solvate using thermogravimetry, differential thermoanalysis as well as differential scanning calorimetry proves, that on solvent removal an amorphous form is obtained that crystallizes into form I on further heating.

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“…The desolvation of solvates is a widely used method of exploring polymorphism of compounds, [61][62][63] but to the knowledge of the authors this is the first example to demonstrate that cocrystal formation/thermal dissociation may provide a method of exploring polymorphism of a compound by giving access to alternate crystallisation conditions. …”

Section: Discussionmentioning

confidence: 99%

Investigation of an Amide-Pseudo Amide Hydrogen Bonding Motif within a Series of Theophylline:Amide Cocrystals

Eddleston

Arhangelskis

Fábián

et al. 2015

Crystal Growth & Design

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The pharmaceutically active compound theophylline (T) was cocrystallized with the amides formamide (1), acetamide (2), N-methylformamide (3), N,N-dimethylformamide (4), benzamide (5), and pyrazinamide (6), with systems T:1, T:5, and T:6 displaying polymorphic behavior. The cocrystals with formamide (T:1), acetamide (T:2), and benzamide (T:5), and one polymorph of the cocrystal with pyrazinamide (T:6-I), contain an R 2 2 (9) hydrogen bonding motif between the amide cocrystal formers and the HN−C−CO moiety of the theophylline molecule (an amide-pseudo amide synthon). This motif was, however, absent from the other polymorph of the pyrazinamide cocrystal (T:6-II) and also from the N-methylformamide cocrystal (T:3) (and is not possible in the N,N-dimethylformamide cocrystal (T:4)). These observations are rationalized using hydrogen bond propensity calculations, although limitations of using such calculations for predicting cocrystallization are noted. The amide-pseudo amide synthon is favored when theophylline cocrystallizes with both primary amides and with secondary amides which are locked in a cis configuration. On heating, all cocrystals were found to dissociate before melting due to loss of the amide, making stability to dissociation a more meaningful measure of cocrystal stability than melting point for these systems. On dissociation of the cocrystals, theophylline typically crystallizes as the commonly observed polymorph Form II. In the case of the acetamide cocrystal (T:2), however, the rarely observed metastable polymorph, Form V, crystallizes concomitantly with Form II suggesting that cocrystal dissociation on heating could be a strategy for identifying novel polymorphic forms of compounds.

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Investigations on the polymorphism and pseudopolymorphism of triamcinolone diacetate

Cited by 20 publications

References 16 publications

Structural, Thermodynamic, and Kinetic Aspectsof the Trimorphism of Hydrocortisone

Structural, Thermodynamic, and Kinetic Aspectsof the Trimorphism of Hydrocortisone

Investigations on the polymorphism and pseudopolymorphism of clobetasone butyrate

Investigation of an Amide-Pseudo Amide Hydrogen Bonding Motif within a Series of Theophylline:Amide Cocrystals

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