Timmermann Flashcards
Labeling alpha or Beta

Number the cholesterol

All the cholesterol compounds we go over are cis or trans? meaning what?
All trans and its talking about the fusion of the rings
Cholestane skeleton?
Example?
Long side chain and 2 methyl on 13 and 10
18, 19 methyl
Cholesterol
6 carbons

Cholane?
Small sidechaine than cholestane 4 carbons
two methyls 18 19

Pregnane
Much smaller side chaine

Estrane nucleus
Absence of 19 carbon

Androstane

Practice

Cholesterol —>? Preg?
What is involved?

Summary of pathway
Where is aromatase involved?

What is armomatase involved in?

What are the biosynthetic steps for Estradiol from Androstenendione
—> Aromatase gives Estrone
17b-HSD —> Estradiol
Estrogens natural sources
- Ovaries
- Plcenta
- Adrenal cortex (males and females)
- Plants (flavoniods)
- Mare urine
Structure activity relationship of Estrogens

Estrane nucleus has no?
C19 carbons
Estrogens aromatic where?
A rings
esterogen group at 3 position?
Subject to?
What does this limit?
- Phenolic hydroxyl
- Subject to biotransformation, which limits the duration of action, sulfation and glucuronidation
Estradiol
rxn via sulfation and glucuronidation products
Estradiol sulfate and estradiol glucuronidate
3-hydroxyl group on estradiol is subject to ______ metabolism especially with ____ and to a lesser extent with?
What do these things cause?
- Phase II metabolism mostly with sulfation but also with glucuronidation
- Sulfation and Glucuronidation increase polarity and cause more renal elimination
What does an ether at the C3 position of an Estrogen cause?
2 things
- Ethers prolong the DOA by preventing sulfation and glucuronidation in vivo
- The ether derivatives are inactive prodrugs that require hepatic dealkylation for activity
Estrogens: 17 a group hydroxl
What happens at the 17b group and what enzyme causes it?
Hepatic oxidation by 17b-hydroxysteroid dehydrogenase
Makes a less active ketone and limits oral activity
Estrogens 17 alpha ethinylation
Blocks?
Permits?

Estrogens 17b OH esterifications
Provides?
Protects?
What happens in tissue?


























































































