Exploring the Polymorphism of Drostanolone Propionate

Abstract

2α-Methyl-4,5α-dihydrotestosterone 17β-propionate, known as drostanolone propionate or masteron, is a synthetic anabolic-androgenic steroid derived from dihydrotestosterone. The crystal structures of two polymorphs of drostanolone propionate have been determined by single crystal X-ray diffraction and both crystallizes in the monoclinic crystal system. One is belonging to the P21 space group, Z = 2, and has one molecule in the asymmetric unit while the second belongs to the I2 space group, Z = 4, and contains two molecules in the asymmetric unit. Another polymorph has been investigated by an X-ray powder diffraction method and solved by Parallel tempering/Monte Carlo technique and refined with the Rietveld method. This polymorph crystallizes in the orthorhombic P212121 space group, Z = 4 having one molecule in the asymmetric unit. The structural configuration analysis shows that the A, B, and C steroid rings exist as chair geometry, while ring D adopts a C13 distorted envelope configuration in all structures. For all polymorphs, the lattice energy has been computed by CLP (Coulomb-London-Pauli), and tight-binding density functional theory methods. Local electron correlation methods were used to estimate the role of electron correlation in the magnitude of the dimer energies. The nature of the intermolecular interactions has been analyzed by the SAPT0 energy decomposition methods as well as by Hirshfeld surfaces.

Structural Aspects and Intermolecular Energy for Some Short Testosterone Esters

“…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 ].…”

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

“…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 ].…”