Chemistry of steroids Flashcards
1
Q
Steroids
A
Derived from lanosterol in animals
Produced in human adrenal glands
All share same 4 membered ring backbone
2
Q
Steroid backbone
A
4 organic rings
A, B, C = 6 membered ring
D = 5 membered ring
Hydroxyls groups - sterols
3
Q
Steroids MOA
A
Act at glucocorticoid receptor
Regulates gene controlling inflammation, development and metabolism
4
Q
Hydrocortisone (cortisol)
A
pKa = 16
OH too strongly bond to dissociate
5
Q
Beclomethasone
A
Adding chlorine increases lipophilicity
Extra methyl increases lipophilicity
6
Q
Budenoside
A
4 carbon tail increases lipophilicity
7
Q
Prednisolone
A
Similar to hydrocortisone with addition of double bonds on ketone ring
8
Q
Rule of five
A
A molecular weight less than 500 Da
No more than 5 H bond donor groups
No more than 10 H acceptor groups
Log P less than 5
