Structural Aspects and Intermolecular Energy for Some Short Testosterone Esters

Abstract

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.

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

“…The literature reports the crystal structures of other shorter testosterone esters, along with their corresponding CCDC Refcodes, as follows: propionate (ZZZRCG01) [ 15 ], buciclate (ETEVII) [ 16 ], non-esterified form (TESTON10) [ 17 ], isocaproate, phenylpropionate and one propionate polymorph (with deposition numbers 2192707, 2192708 and 2192706) [ 18 ] and also acetate (TELYEO) [ 19 ]. Apart from testosterone esters, the crystal structures of other testosterone derivatives were also investigated [ 20 , 21 , 22 ].…”

Synthesis, Physicochemical Characterization and Applications of Advanced Nanomaterials

“…The study by Turza et al [ 18 ] showed the structural aspects and intermolecular energy of some short testosterone esters. Testosterone (17β-Hydroxyandrost-4-en-3-one) is the primary male anabolic–androgenic steroid.…”

“…They were shown to belong to the non-centrosymmetric orthorhombic P2 1 2 1 2 1 , and monoclinic P2 1 space groups. Structural features were described and evaluated in terms of Hirshfeld surfaces, and crystal energies were further compared with the base native form (without ester) and with the acetate ester [ 18 ]. The investigation of crystals in the solid state via computational methods yielded that, in all crystals, the crystal stability and formation of supramolecular self-assemblies are governed by dominant dispersion effects.…”

“…The investigation of crystals in the solid state via computational methods yielded that, in all crystals, the crystal stability and formation of supramolecular self-assemblies are governed by dominant dispersion effects. Although the C-H-O hydrogen bonds are present in all compounds, they play a less noticeable role [ 18 ]. Total crystal lattice energies are greater in absolute terms with the increase in ester chain length.…”

“…The shortest acetate ester possesses the lowest solubility, while the longest isocaproate ester is approximately four-fold greater. Phenylpropionate and propionate forms show similar values and are between the other two [ 18 ].…”