Structural studies of some androstane based prodrugs

Turza, Alexandru; Borodi, Gheorghe; Pop, Alexandra; David, Maria

doi:10.1016/j.molstruc.2021.131440

Cited by 6 publications

(3 citation statements)

References 26 publications

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“…Similar crystal lattice behaviour in the sense that the dispersion term dominates the crystals, and the total energy becomes greater with the increase in ester length has been previously reported in other anabolic–androgenic agents from the steroid group [ 36 , 37 , 38 , 39 ].…”

Section: Resultssupporting

confidence: 76%

Structural Aspects and Intermolecular Energy for Some Short Testosterone Esters

et al. 2022

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Testosterone (17β-hydroxyandrost-4-en-3-one) is the primary naturally occurring anabolic–androgenic steroid. The crystal structures of three short esterified forms of testosterone, including propionate, phenylpropionate, and isocaproate ester, were determined via single-crystal X-ray diffraction. Furthermore, all the samples were investigated using powder X-ray diffraction, and their structural features were described and evaluated in terms of crystal energies and Hirshfeld surfaces. They were also compared with the base form of testosterone (without ester) and the acetate ester. Moreover, from a pharmaceutical perspective, their solubility was evaluated and correlated with the length of the ester.

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Section: Resultssupporting

confidence: 76%

Structural Aspects and Intermolecular Energy for Some Short Testosterone Esters

et al. 2022

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“…In all four crystal structures, among the attractive terms the dispersion energy plays the most important role, the stacking of the steroid backbone providing a large contribution to this. This feature has been reported in other androstane derivatives (Turza et al, 2019(Turza et al, , 2022bBorodi et al, 2020a,b).…”

Section: Crystal Structure Energy Analysissupporting

confidence: 80%

Solid forms and β-cyclodextrin complexation of turinabol

Turza

Ulici

Mureşan-Pop

et al. 2022

Acta Crystallogr C Struct Chem

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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).

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“…Previous reports in the literature show comparable results of other agents from the steroid family, where dispersion terms play the dominant role and the total energy increases with the increase in ester length [ 31 , 32 , 33 , 34 ].…”

Section: Resultssupporting

confidence: 63%

Structural Insights and Intermolecular Energy for Some Medium and Long-Chain Testosterone Esters

et al. 2023

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Testosterone (17β-Hydroxyandrost-4-en-3-one) is the primary male anabolic-androgenic steroid. The crystal structures of two medium and two long esterified forms of testosterone, including enanthate, cypionate, decanoate and undecanoate, were determined by X-ray single crystal diffraction. The samples were also characterized by powder X-ray diffraction, FT-IR spectroscopy and thermal analysis (DTA, TG). Crystal packings and supramolecular features were described. The analysis of structural features was accomplished by computational methods in terms of the type of intermolecular interactions, crystal energies and Hirshfeld surfaces analysis. From a pharmaceutical point of view, the solubility of compounds was investigated.

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Structural studies of some androstane based prodrugs

Cited by 6 publications

References 26 publications

Structural Aspects and Intermolecular Energy for Some Short Testosterone Esters

Structural Aspects and Intermolecular Energy for Some Short Testosterone Esters

Solid forms and β-cyclodextrin complexation of turinabol

Structural Insights and Intermolecular Energy for Some Medium and Long-Chain Testosterone Esters

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