A series of $3{eta}$-substituted 5-androstene-$17{eta}$-carboxamides were synthesized from analogs of $3{eta}$-hydroxy-5-androstene-$17{eta}$-carboxylic acid (1) with tert-butylamine, N,N-diethylamine and 3-aminopyridine and some compounds were epoxidized with mCPBA. A rat prostate testosterone $5{alpha}$-reductase inhibitory activity of synthesized compounds was assessed by radioimmunoassay using [1,2,6,7-3H]-testosterone as substrate. All synthesized compounds showed lower activity than finasteride and the N-(3-pyridino)-$3{eta}$-carboxycarbonyloxy-5-androstene-$17{eta}$-carboxamide (12) showed weak inhibitory activity ($IC_{50}$: $2.4{ imes}10^{-7}M$).