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

Abstract

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.

Crystal Structure and Intermolecular Energy for Some Nandrolone Esters

“…Similar solubilities were reported for the analogue esters of testosterone: 175.5 mg/mL for testosterone propionate, 139 mg/mL for testosterone phenylpropionate [30], 255 mg/mL for testosterone cypionate and 197 mg/mL for the undecanoate ester of testosterone [31].…”

“…Endothermic peaks are present at 78 °C for NPro, 102 °C for NPhp, 33 and 66 °C in two steps for NCyp and 66 °C for NUnd; these indicate the melting points of the compounds. Note that, for NCyp, its texture shows a clay-like appearance and possesses Similar solubilities were reported for the analogue esters of testosterone: 175.5 mg/mL for testosterone propionate, 139 mg/mL for testosterone phenylpropionate [30], 255 mg/mL for testosterone cypionate and 197 mg/mL for the undecanoate ester of testosterone [31].…”

Contemporary treatment options for male hypogonadism

“…Czas półtrwania estru testosteronu zwiększa się wraz ze wzrostem wielkości łańcucha węglowego.Najkrótszy czas półtrwania wynoszący około 20 godzin oraz 3 atomy węgla w łańcuchu bocznym posiada propionian testosteronu. Undecylanian testosteronu ma 11 atomów węgla w łańcuchu bocznym, a jego czas półtrwania sięgający 34 dni pozwala na stosowanie go raz na 10-14 tygodni [19,20]. W ostatnich badaniach wykazano, że enantan oraz cypionian testosteronu podawany w iniekcjach podskórnych, do tkanki tłuszczowej raz w tygodniu, może być alternatywą do preparatów stosowanych domięśniowo [21].…”