Steroids Overall Organization of the Lecture Series Introduction

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Presentation transcript:

Steroids Overall Organization of the Lecture Series Introduction - Structure, Nomenclature, Conformation, Configuration Hypercholesterolemia - Cholesterol, Anti-hyperlipidemic Agents Male Sex Hormones - Androgens Female Sex Hormones - Estrogens and Progestins Adrenocorticoids - Anti-inflammatory and Salt Retaining Agents 11/29/2018 MEDC 603 Steroids

Examples of Steroid-based Drugs in Use Today Male Sex Hormone Female Sex Hormone Congested Heart Symptoms Anti-inflammatory Agent 11/29/2018 MEDC 603 Steroids

Structures of Steroids Structure and Nomenclature of the Steroid Nucleus 18 CH3 12 15 16 17 19 11 13 A B C D 1 8 9 2 14 10 3 6 7 5 4 11/29/2018 MEDC 603 Steroids

Structures of Steroids Structure and Nomenclature of the Steroid Side-chain 21 22 20 26 27 23 24 25 11/29/2018 MEDC 603 Steroids

Configurational Isomers of Steroids Fusion points between rings A B A B trans- configuration cis- configuration 11/29/2018 MEDC 603 Steroids

Configurational Isomers of Steroids Fusion points between rings A B C D 3 fusion points  23 isomers = 8 11/29/2018 MEDC 603 Steroids

Configurational Isomers of Steroids Three dimensional structure of three most common isomers trans-trans-trans cis-trans-trans cis-trans-cis 11/29/2018 MEDC 603 Steroids

Nomenclature of Steroids a- and b- configuration and numbering 11/29/2018 MEDC 603 Steroids

Nomenclature of Steroids a- and b- configuration and numbering 11/29/2018 MEDC 603 Steroids

Biosynthesis and Metabolism of Cholesterol CH3-C-SCoA -OOC-CH2-C-CH2-C-SCoA O OH CH3 acetyl coenzyme A 3-hydroxy-3-methyl-glutaryl-CoA HMG CoA reductase cholesterol -OOC-CH2-C-CH2-CH2-OH OH CH3 mevalonate 11/29/2018 MEDC 603 Steroids

Biosynthesis and Metabolism of Cholesterol liver various tissues Bile Acids (cholic acid, desoxy cholic acid, etc.) Hormones (testosterone, progesterone cortisol, estradiol, etc.) 11/29/2018 MEDC 603 Steroids