17β-Hydroxy-17α-methylandrostano[3,2-c]pyrazole, Stanozolol: The Crystal Structures of Polymorphs 1 and 2 and 10 Solvates

Karpinska, Jolanta; Erxleben, Andrea; McArdle, Patrick

doi:10.1021/cg101651p

Cited by 29 publications

(51 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A void in a structure can be defined as a region that can accommodate at least a sphere of radius 1.2 A ˚without intersecting with any of the van der Waals spheres assigned to each atom in the structure (Spek, 2015). Similar structural voids were reported in polymorphs of stanozolol (Karpinska et al, 2011) and methyldrostanolone (Turza et al, 2022a), which are agents also belonging to the steroid group. The crystal structure stability of TBOL-2 is supported by intermolecular interactions between the two molecules in the asymmetric unit with a magnitude of À68.1 kJ mol À1 .…”

Section: (B)]supporting

confidence: 76%

Solid forms and β-cyclodextrin complexation of turinabol

Turza

Ulici

Mureşan-Pop

et al. 2022

Acta Crystallogr C Struct Chem

View full text Add to dashboard Cite

4-Chloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one (C20H27ClO2), known as turinabol, is a synthetic anabolic–androgenic agent which belongs to the steroid class. Recrystallization from various solvents was performed and the following new solid forms of turinabol were obtained: the hemihydrate (C20H27ClO2·0.5H2O), the anhydrous form (C20H27ClO2), the multicomponent acetic acid hydrate (2C20H27ClO2·C2H4O2·H2O) and the 2,2,2-trifluoroethanol hemisolvate (C20H27ClO2·0.5C2H3F3O). The absolute structures were determined by single-crystal X-ray diffraction. The starting hemihydrate form contains one turinabol molecule in the asymmetric unit, while the others contain two molecules in the asymmetric unit. Structural features were investigated in terms of the conformational analysis of the steroid skeleton rings and intermolecular interactions. The magnitudes, the nature of the crystal structure energies and the intermolecular interactions were also evaluated. Complexation with β-cyclodextrin was performed and the obtained complex was investigated using powder X-ray diffraction, Fourier-transform infrared (FT–IR) spectroscopy and differential thermal analysis/thermogravimetric analysis (DTA/TGA).

show abstract

Section: (B)]supporting

confidence: 76%

Solid forms and β-cyclodextrin complexation of turinabol

Turza

Ulici

Mureşan-Pop

et al. 2022

Acta Crystallogr C Struct Chem

View full text Add to dashboard Cite

show abstract

“…The relatively low packing indices of the NaTC structures are typical of steroid and other molecules which have an awkward shape and can be difficult to crystallize from solution without solvent molecules in the lattice. Solvent free crystals for some steroids can be grown by sublimation but often contain voids (Karpinska et al, 2011). This packing difficulty combined with a high hydrogen bonding capacity (OH, C=O, amide-NH, sulfonyl-O) makes NaTC suitable for the formation of coamorphous API-NaTC systems.…”

Section: Resultsmentioning

confidence: 99%

The natural bile acid surfactant sodium taurocholate (NaTC) as a coformer in coamorphous systems: Enhanced physical stability and dissolution behavior of coamorphous drug-NaTc systems

Gniado

MacFhionnghaile

McArdle

et al. 2018

International Journal of Pharmaceutics

Self Cite

View full text Add to dashboard Cite

“…19 2.1.2 Sublimation onto polycrystalline powder templates. Following the successful application of sublimation to the production of the first solvent free single crystals of stanozolol and ethinylestradiol 20,21 and the interesting report of the use of a single crystal template for polymorph control during sublimation 22 we decided to modify our sublimation apparatus to allow the use of polycrystalline powder templates for polymorph control. 13 Almost simultaneously and in an attempt to improve the polymorph control produced by single crystals the use of liquid drop cast polycrystalline film templates for sublimation at atmospheric pressure was reported.…”

Section: Form Bmentioning

confidence: 99%

Use of Sublimation Catalysis and Polycrystalline Powder Templates for Polymorph Control of Gas Phase Crystallization

Kamali

O’Malley

Mahon

et al. 2018

Crystal Growth & Design

Self Cite

View full text Add to dashboard Cite

In pursuit of a solvent free green alternative to solution based processes, we have applied the combined use of catalytic additives and polycrystalline powder templates for polymorph control of gas phase crystallization to a range of pharmaceuticals and related compounds. Complementary volatile additives have been found which can catalyse the sublimation of a range of typical active pharmaceutical ingredients, APIs. Sublimation temperatures are typically reduced by up to 20 °C and the process is accelerated. The use of polycrystalline powder templates for polymorph control has also been successfully applied in several cases. Temperature control at the sites of both sublimation and desublimation is often required. The absence of even traces of solvent in the polymorphs produced appears to give the samples higher stability than samples obtained by crystallization from solution. Complete polymorph control was achieved with the following APIs, carbamazepine (5 polymorphs), metaxalone (2 polymorphs), mefenamic acid (2 polymorphs), paracetamol (2 polymorphs) and ortho-, meta-and para-amino benzoic acids (1, 4 and 2 polymorphs respectively).

show abstract

17β-Hydroxy-17α-methylandrostano[3,2-c]pyrazole, Stanozolol: The Crystal Structures of Polymorphs 1 and 2 and 10 Solvates

Cited by 29 publications

References 18 publications

Solid forms and β-cyclodextrin complexation of turinabol

Solid forms and β-cyclodextrin complexation of turinabol

The natural bile acid surfactant sodium taurocholate (NaTC) as a coformer in coamorphous systems: Enhanced physical stability and dissolution behavior of coamorphous drug-NaTc systems

Use of Sublimation Catalysis and Polycrystalline Powder Templates for Polymorph Control of Gas Phase Crystallization

Contact Info

Product

Resources

About