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Androgenic Steroids

Androgenic Steroids. Overall Organization of the Topic. Overall mechanism of steroid hormone action Structure of male sex hormones - Testosterone, androstendione, and 5 a -dihydrotestosterone Nomenclature of androgenic steroids Physiological activities

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Androgenic Steroids

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

  2. (intranuclear) dimerization DNA (intracellular) transcription translation proteins Intracellular effects extracellular effects Steroid Hormones Overall Mechanism of Steroid Hormone Action (extracellular)

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

  4. 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

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

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

  7. Structure Activity Relationships in Androgens Anabolic Androgenic Testosterone 1 1 (injectable) Testosterone 1 1 esters (injectable) R = COCH2CH3 propionate = CO(CH2)5CH3 enanthate = COCH2CH2(C5H9) cypionate

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

  9. Structure Activity Relationships in Androgens Anabolic Androgenic Nandrolone 2.5 1 (injectable) Oxymetholone 2.5 1 (oral)

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

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

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

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