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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 MEDC 603 Steroids

  2. (intranuclear) dimerization DNA (intracellular) transcription translation proteins Intracellular effects extracellular effects Steroid Hormones Overall Mechanism of Steroid Hormone Action (extracellular) MEDC 603 Steroids

  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 MEDC 603 Steroids

  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 MEDC 603 Steroids

  5. Androgenic Steroids - Physiological Activities Andro is available over the counter!! MEDC 603 Steroids

  6. Biosynthesis and Metabolism of Testosterone Testosterone Cholesterol Pregnenolone Other metabolites Androstendione 5a-DHT MEDC 603 Steroids

  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 MEDC 603 Steroids

  8. Structure Activity Relationships in Androgens Anabolic Androgenic 17a-methyl Testosterone 1 1 (oral) Fluoxymesterone 1 1 (oral) MEDC 603 Steroids

  9. Structure Activity Relationships in Androgens Anabolic Androgenic Nandrolone 2.5 1 (injectable) Oxymetholone 2.5 1 (oral) MEDC 603 Steroids

  10. Structure Activity Relationships in Androgens Anabolic Androgenic Stanozolol 3 1 (oral) Dromostanolone 4 1 (oral) MEDC 603 Steroids

  11. Structure Activity Relationships in Androgens Generalizations • Steroid skeleton is necessary • An electronegative (may not be oxygen) at 3 position is required • A/B ring fusion should be either trans or presence of a double bond at 4 position • Alkyl group (CH3) at 17a-position is necessary for anabolic activity • Alkyl group at 17a- confers oral activity MEDC 603 Steroids

  12. Androgens Antagonists Danazol (endometriosis) Finesteride (baldness) Bicalutamide (prostate cancer) Flutamide (prostate cancer) MEDC 603 Steroids

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