Steroids Overall Organization of the Lecture Series Introduction

Steroids Overall Organization of the Lecture Series Ö Introduction - Structure, Nomenclature, Conformation, Configuration Ö Hypercholesterolemia - Cholesterol, Anti-hyperlipidemic Agents Ö Male Sex Hormones - Androgens Ö Female Sex Hormones - Estrogens and Progestins Ö Adrenocorticoids - Anti-inflammatory and Salt Retaining Agents 11/2/2020 MEDC 603 Steroids 1

Examples of Steroid-based Drugs in Use Today Male Sex Hormone Female Sex Hormone Anti-inflammatory Agent Congested Heart Symptoms 11/2/2020 MEDC 603 Steroids 2

Structures of Steroids Structure and Nomenclature of the Steroid Nucleus 18 19 11 1 2 A 3 4 11/2/2020 CH 3 10 5 9 B 12 CH 3 17 C 13 D 16 8 14 15 7 6 MEDC 603 Steroids 3

Structures of Steroids Structure and Nomenclature of the Steroid Side-chain 21 22 20 23 24 26 25 27 11/2/2020 MEDC 603 Steroids 4

Configurational Isomers of Steroids Fusion points between rings A B trans- configuration 11/2/2020 MEDC 603 Steroids A B cis- configuration 5

Configurational Isomers of Steroids Fusion points between rings C A D B 3 fusion points 23 isomers = 8 11/2/2020 MEDC 603 Steroids 6

Configurational Isomers of Steroids Three dimensional structure of three most common isomers trans-trans cis-trans-cis 11/2/2020 MEDC 603 Steroids 7

Nomenclature of Steroids a- and b- configuration and numbering 11/2/2020 MEDC 603 Steroids 8

Nomenclature of Steroids a- and b- configuration and numbering 11/2/2020 MEDC 603 Steroids 9

Biosynthesis and Metabolism of Cholesterol O CH 3 -C-SCo. A -OOC-CH O 2 -C-CH 2 -C-SCo. A OH 3 -hydroxy-3 -methyl-glutaryl-Co. A acetyl coenzyme A HMG Co. A reductase CH 3 -OOC-CH 2 -CH 2 -OH OH mevalonate cholesterol 11/2/2020 MEDC 603 Steroids 10

Biosynthesis and Metabolism of Cholesterol cholesterol liver Bile Acids (cholic acid, desoxy cholic acid, etc. ) 11/2/2020 various tissues Hormones (testosterone, progesterone cortisol, estradiol, etc. ) MEDC 603 Steroids 11