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
11/27/2018
MEDC 603 Steroids

2. Steroid Hormones Overall Mechanism of Steroid Hormone Action
(intracellular)
(intranuclear)
proteins
Intracellular effects
extracellular effects
transcription
translation
dimerization
DNA
(extracellular)
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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
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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
11/27/2018
MEDC 603 Steroids

5. Androgenic Steroids - Physiological Activities
Andro is available over the counter!!
11/27/2018
MEDC 603 Steroids

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

7. Structure Activity Relationships in Androgens
Anabolic Androgenic
Testosterone
(injectable)
Testosterone
esters (injectable)
R = COCH2CH propionate
= CO(CH2)5CH enanthate
= COCH2CH2(C5H9) cypionate
11/27/2018
MEDC 603 Steroids

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

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

10. Structure Activity Relationships in Androgens
Anabolic Androgenic
Stanozolol
(oral)
Dromostanolone
(oral)
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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
11/27/2018
MEDC 603 Steroids

12. Androgens Antagonists
Danazol
(endometriosis)
Finesteride
(baldness)
Bicalutamide
(prostate cancer)
Flutamide
(prostate cancer)
11/27/2018
MEDC 603 Steroids