Quantum Chemical Studies of Anti-Prostatic Carcinoma Drug N-[4-cyano3-(trifluoromethyl)phenyl]-2-hydroxy-2-methyl-3-[(4methylphenyl)sulfonyl] Propanamide (bicalutamide)

• Published in: Research journal of pharmacognosy and phytochemistry Vol. 7; no. 4; pp. 214 - 218
• Main Authors: Otuokere, I.E, Amaku, F J
• Format: Journal Article
• Language: English
• Published: Raipur A & V Publications 01.10.2015; A&V Publications
• Subjects: Arguslab software; bicalutamide; receptors; steric energy; surfaces
• ISSN: 0975-2331; 0975-4385
• DOI: 10.5958/0975-4385.2015.00032.1

N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methyl-3-[(4-methylphenyl)sulfonyl]propanamide (bicalutamide) is an oral medication that is used for treating cancer of the prostate. It belongs to a class of drugs called anti-androgens. Quantum chemical studies of bicalutamide were based on Arguslab software. The steric energy was evaluated in terms of potential energy as a sum of energies associated with bonded interactions (bond length, bond angle and dihedral angle) as well as non-bonded interactions (van der Waals and electrostatic). Surfaces were created to visualize excited state properties such as highest occupied molecular orbital's, lowest unoccupied molecular orbital's and electrostatic potential (ESP) mapped density. The steric energy for bicalutamide was calculated to be 0.963933 a.u. (604.877867 kcal/mol). The most energetically favourable conformation of bicalutamide was found to have a heat of formation of 7696.375900 kcal/mol. The self-consistent field (SCF) energy was calculated by geometry convergence function using RHF/PM3 method in ArgusLab software. The most feasible position for bicalutamide to block androgen receptors on the cells of tissues was found to be-189.888176 au (−119156.737100 Kcal/mole).