Androgenic Steroids Overall Organization of the Topic Overall

Androgenic Steroids Overall Organization of the Topic Ö Overall mechanism of steroid hormone action Ö Structure of male sex hormones - Testosterone, androstendione, and 5 a-dihydrotestosterone Ö Nomenclature of androgenic steroids Ö Physiological activities - Androgenic and anabolic activities Ö Biosynthesis and metabolism of testosterone Ö Structure activity relationships - Generalizations Ö Androgen antagonists - Finasteride, danazol, bicalutamide and flutamide

Steroid Hormones Overall Mechanism of Steroid Hormone Action (extracellular) (intranuclear) dimerization A DN (intracellular) transcription translation Intracellular effects proteins extracellular effects

Androgenic Steroids Structure and Nomenclature Testosterone (17 b-hydroxy-androst-4 -en-3 -one) 3 D-structure Androstendione (Andro) (androst-4 -en-3, 17 -dione) 5 a-Dihydro-testosterone (17 b-hydroxy-5 b-androstan-3 -one) 3 D-structure

Androgenic Steroids – Physiological Activities Primarily two activities – Androgenic and Anabolic Androgenic Activity • • Growth and development of male sex organs Important for male sex drive and performance Development of secondary sexual characteristics Important role in spermatogenesis Anabolic Activity • • Development of muscle mass Reverse catabolic or tissue-depleting processes

Androgenic Steroids - Physiological Activities Andro is available over the counter!!

Biosynthesis and Metabolism of Testosterone Cholesterol Other metabolites Pregnenolone Testosterone 5 a-DHT Androstendione

Structure Activity Relationships in Androgens Anabolic Testosterone (injectable) Androgenic 1 1 Testosterone 1 esters (injectable) 1 R = COCH 2 CH 3 propionate = CO(CH 2)5 CH 3 enanthate = COCH 2(C 5 H 9) cypionate

Structure Activity Relationships in Androgens Anabolic 17 a-methyl Testosterone (oral) Fluoxymesterone (oral) 1 1 Androgenic 1 1

Structure Activity Relationships in Androgens Anabolic Nandrolone (injectable) Oxymetholone (oral) 2. 5 Androgenic 1 1

Structure Activity Relationships in Androgens Anabolic Stanozolol (oral) 3 Dromostanolone (oral) Androgenic 1 4 1

Structure Activity Relationships in Androgens 17 a-methyl testosterone (10 -50 mg/day) Oxandrolone (5 -10 mg/day) Norethandrolone 10 -30 mg/day Ethylestrenol (4 mg/day) Methenolone acetate (20 mg /wk) Chlorotestosterone acetate (20 mg / wk)

Androgens Antagonists Danazol (endometriosis) Bicalutamide (prostate cancer) Finesteride (baldness) Flutamide (prostate cancer)