Embed Size (px)
DESCRIPTION
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 - PowerPoint PPT Presentation
Citation preview
Androgenic SteroidsAndrogenic Steroids
Overall Organization of the Topic
Overall mechanism of steroid hormone action Structure of male sex hormones
- Testosterone, androstendione, and 5-
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
Steroid HormonesSteroid Hormones
Overall Mechanism of Steroid Hormone Action
(extracellular)
(intracellular)
(intranuclear)
proteinsIntracellular effects
extracellular effects
transcriptiontranslation
dimerization
DNA
Androgenic SteroidsAndrogenic Steroids
CH3
OH
O
CH3
CH3
O
CH3O
CH3
OH
O
CH3
H
Androstendione(Andro)
5-Dihydro-testosterone
Testosterone
Structure and Nomenclature
(17-hydroxy-androst-4-en-3-one)3D-structure (androst-4-en-3,17-dione)
(17-hydroxy-5-androstan-3-one)3D-structure
Androgenic Steroids – Physiological ActivitiesAndrogenic Steroids – Physiological Activities
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
Primarily two activities – Androgenic and Anabolic
Anabolic Activity
• Development of muscle mass• Reverse catabolic or tissue-depleting processes
Andro is available over the counter!!
Androgenic Steroids - Physiological Androgenic Steroids - Physiological ActivitiesActivities
Biosynthesis and Metabolism of TestosteroneBiosynthesis and Metabolism of Testosterone
CH3
CH3
OH
CH3
CH3CH3
O
OH
CH3
CH3OH
O
CH3
O
CH3O
CH3
OH
O
CH3
H
CH3
CH3
HOH
OH
Cholesterol Pregnenolone Testosterone
Androstendione5-DHTOther metabolites
Structure Activity Relationships in AndrogensStructure Activity Relationships in Androgens
CH3
OH
O
CH3Anabolic Androgenic
Testosterone 1 1(injectable)
CH3
OR
O
CH3
Testosterone 1 1esters (injectable)
R = COCH2CH3 propionate
= CO(CH2)5CH3 enanthate
= COCH2CH2(C5H9) cypionate
Structure Activity Relationships in AndrogensStructure Activity Relationships in Androgens
CH3
OH
O
CH3CH3
Anabolic Androgenic
17-methylTestosterone 1 1(oral)
CH3
OH
O
CH3OH
F
CH3
Fluoxymesterone 1 1(oral)
Structure Activity Relationships in AndrogensStructure Activity Relationships in Androgens
Anabolic Androgenic
Nandrolone 2.5 1(injectable)
H
OH
O
CH3
CH3
OH
O
CH3CH3
OH
H
Oxymetholone 2.5 1(oral)
Structure Activity Relationships in AndrogensStructure Activity Relationships in Androgens
Anabolic Androgenic
Stanozolol 3 1(oral)
Dromostanolone 4 1(oral)
CH3
OH
N
CH3CH3
NH
H
CH3
OH
O
CH3
H
CH3
CH3
Structure Activity Relationships in AndrogensStructure Activity Relationships in Androgens
CH3
OHCH3CH2CH3
H
OHCH3CH2CH3
O
CH3
OCOCH3
O
CH3
H
CH3
CH3
OCOCH3
O
CH3
Cl
O
CH3
OH
O
CH3CH3
H
Ethylestrenol (4 mg/day)
Norethandrolone10-30 mg/day
Methenolone acetate (20 mg /wk)
Chlorotestosterone acetate (20 mg / wk)
Oxandrolone (5-10 mg/day)
CH3
OH
O
CH3CH3
17-methyl testosterone(10-50 mg/day)
Androgens AntagonistsAndrogens Antagonists
NH
CF3
S
F
CN
O O O
CH3OHNH
CF3
O
CH3
NO2
CH3
O
CH3
CH3OH
CH
N
CH3
CH3
NH
O
O
NH
CH3CH3CH3
HDanazol
(endometriosis)Finesteride(baldness)
Bicalutamide(prostate cancer)
Flutamide(prostate cancer)
