Steroids Overall Organization of the Lecture Series

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Steroids Overall Organization of the Lecture Series

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Presentation transcript:

Steroids Overall Organization of the Lecture Series Structure, Nomenclature, Conformation, Configuration Anti-Hyperlipidemic Agents Androgens Estrogens and Progestins Anti-inflammatory Steroids and Salt Retaining Agents

Examples of Steroid-based Drugs in Use Today Male Sex Hormone Female Sex Hormone Congested Heart Symptoms Anti-inflammatory Agent

Functional Classification of Steroids Anabolic Steroids - Interact with androgen receptor; enhance muscle mass/athlete’s performance; male sex hormones Glucocorticoids - regulate metabolism and immune function; anti-inflammatory activity Mineralocorticoids - maintain blood volume and renal excretion Progestins - Development of female sex organs and characteristics Phytosteroids - Plant steroids Ergosteroids - Steroids of the fungi; vitamin D related

Structures of Steroids Structure and Nomenclature of the Steroid Nucleus CH3 A B C D 20 21 22 23 24 25 26 27

Configurational Isomers of Steroids Fusion points between rings A B A B trans- configuration cis- configuration

Configurational Isomers of Steroids Fusion points between rings A B C D 3 fusion points  23 isomers = 8

Configurational Isomers of Steroids Three dimensional structure of three most common isomers trans-trans-trans cis-trans-trans trans-trans-trans cis-trans-trans cis-trans-cis cis-trans-cis

Nomenclature of Steroids a- and b- configuration and numbering

Nomenclature of Steroids a- and b- configuration and numbering

Nomenclature of Steroids Number of Nuclear Positions and Steroid Classification C-27 skeleton … Cholestanes C-24 skeleton … Cholanes C-21 skeleton … Pregnanes C-19 skeleton … Androstanes C-18 skeleton … Estranes

Nomenclature of Steroids Usage of ‘Nor’ terminology C-27 skeleton … Cholestanes 18-Nor C-27 skeleton … 18-nor cholestane C-19 skeleton … Androstanes 19-Nor C-19 skeleton … 19-nor androstane