Lecture 7 - Chemistry of Steroids Flashcards
What are steroids?
Hormone molecules which control many biological events
Examples of steroids and what they control?
Sex hormones, inflammation, immunomodulation, stress and more
What are steroids derived from?
Lanosterol in animals
Where are steroids produced?
In human adrenal glands
Glucocorticosteroids important in?
Controlling inflammation
corticosteroids
What do all steroids share?
The same 4 membered ring backbone
Steroid backbone structure?
Organic 4 ring containing compound
various functional groups attached to the rings
with hydroxyl groups known an sterols
What is the lipinski rule of 5?
Orally absorbed drugs normally observe factors that are multiples of 5
a molecular weight of less than 500
no more than 5 hydrogen bond donor groups
no more than 10 hydrogen bond acceptors
a calculated log P of less than 5
Hydrocortisone physiochemistry?
MWt = 362
log P = 0.5
3 H bond donors
5 H bond acceptors
Beclomethasone physiochemistry?
MWt = 408
log P = 1.24
3 H bond donors
5 H bond acceptors
Budesonide physiochemistry?
MWt = 430
log P = 1.5
2 H bond donors
6 H bond acceptors
Where do hydrocortisone, beclomethasone and budesonid absorb?
in the stomach and the intestine
they do not have acid or basic groups so they are neutral
Where to corticosteroids work?
at the glucocoticoid receptor
What do corticosteroids regulate?
genes controlling inflammation
also regulates genes that control development, metabolism
Where are corticosteroids expressed?
in every cell in the body in different forms
