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

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MEDC 603 Steroids

Examples of Steroid-based Drugs in Use Today

Male Sex
Hormone

CH3 OH

Female Sex
CH3
Hormone

CH3

O
CH3

CH3

Anti-inflammatory O
Agent
CH3
HO
CH3

CH2OH

CH3

OH

CH3
OH
HO

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MEDC 603 Steroids

Congested Heart
Symptoms

Structures of Steroids
Structure and Nomenclature of the Steroid Nucleus
18

19 11
1
2

3
4

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CH3
10
5

12

CH3
17

C 13 D

16

8 14
15
7

MEDC 603 Steroids

Structures of Steroids
Structure and Nomenclature of the Steroid Side-chain
21

CH3
CH3
CH3

22

20

26

23

CH3

24

25

CH3

27

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MEDC 603 Steroids

Configurational Isomers of Steroids

Fusion points between rings

H
trans- configuration

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MEDC 603 Steroids

cis- configuration

Configurational Isomers of Steroids

Fusion points between rings

CH3 R
CH3 C
A

3 fusion points 23 isomers = 8

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MEDC 603 Steroids

Configurational Isomers of Steroids

Three dimensional structure of three most common isomer

CH3

CH3

CH3

R
H

H
trans-trans-trans

cis-trans-trans

CH3
H

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CH3

CH3
H

H
cis-trans-cis

R
H

MEDC 603 Steroids

Nomenclature of Steroids
- and - configuration and numbering

CH3
CH3
CH3

CH3
CH3

HO

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MEDC 603 Steroids

Nomenclature of Steroids
- and - configuration and numbering

O
HO
CH3

CH3

CH2OH
OH

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MEDC 603 Steroids

Biosynthesis and Metabolism of Cholesterol

O

CH3

CH3-C-SCoA

OOC-CH2-C-CH2-C-SCoA

OH
3-hydroxy-3-methyl-glutaryl-CoA

acetyl coenzyme A

HMG CoA
reductase
CH3

CH3

CH3
CH3

CH3

OOC-CH2-C-CH2-CH2-OH

CH3
HO

OH
mevalonate

cholesterol

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MEDC 603 Steroids

10

Biosynthesis and Metabolism of Cholesterol

CH3
CH3
CH3

CH3
CH3

HO

cholesterol

liver

various tissues

Bile Acids
(cholic acid, desoxy
cholic acid, etc.)

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Hormones
(testosterone, progesterone
cortisol, estradiol, etc.)

MEDC 603 Steroids

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