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What is the general structure of estrogens?
aromatic ring, 3-OH, 17-OH, lacks 19-methyl
What is needed for action of estrogens?
3-OH, 17-OH
What is the potency from high to low for estrogens?
estradiol > estrone > estriol
What is the general structure of estradiol?
3-OH, 17-OH
What is the general structure of estrone?
3-OH, 17-ketone
What is the general structure of estriol?
3-OH, 17-OH, 16-OH
What is the irreversible metabolism of estradiol?
sodium sulfate ester of estrone
What is the general structure of sodium sulfate ester of estrone?
estrone + sodium sulfate on C3
What is the reversible metabolism of estradiol?
sodium glucuronide of estriol
What is the general structure of sodium glucuronide of estriol?
estriol + glucuronide on C16
What is the ADME of estrogen?
undergoes enterohepatic cycling and reabsorbed in GI
What is the activating enzyme of estrogen?
bacterial glucuronidase
What are endogenous estrogens?
estradiol, estrone, estriol
What are conjugated/esterified estrogens?
sodium sulfate on C3, estrone structure, prodrug
What is the difference between esterified and conjugated estrogens?
esterified has more sodium estrone than sodium equilin ratio compared to conjugated
What is the difference in structure for estropipate?
negative charge due to piperazine
What is the difference for estrogen esters?
esters on C3 or C17 = prodrug
What is the difference for semisynthetic estrogens?
alkene on C17
What is the purpose of the alkene on C17 in semisynthetic estrogens?
prevent becoming less potent estrogen = improve metabolic stability
What is the difference of mestranol (semisynthetic estrogen)?
prodrug due to methoxy on C3
What is the general structure of pregnanes?
21 carbons, 19-methyl, 17-ethyl
What is the general structure of androstanes?
19 carbons, 19-methyl, 17-H
What is the general structure of estranes?
18 carbons, 19-H, 17-H
What is the general structure of progestins?
3-ketone, 17-ketone, C4=C5
What is the pharm class of pregnane derivatives?
agonist
What agents are pregnane derivatives?
medroxyprogesterone acetate
What is the general structure of medroxyprogesterone acetate?
17-acetyl = long duration, 6-methyl = metabolic stability
What agents are 19-norandrostanes?
nor-, ethynodiol acetate, levonorgestrel, desogestrel, dienogest
What is the general structure of 19-norandrostanes?
3-ketone, 19-H, 17-OH, C4=C5, 18-ethyl, 17-ethylene
What is the purpose of 19-methyl in 19-norandrostanes?
more androgenic ADR
What is the purpose of 19-H in 19-norandrostanes?
increase progesterone activity, decrease androgenic activity
What is the purpose of 3/19-acetyl group or 3-H in 19-norandrostanes?
prodrug
What is the purpose of 18-ethyl in 19-norandrostanes?
decrease ADR
What is the purpose of the C5-C10 double bond in 19-norandrostanes?
decrease ADR
What is the purpose of 3-oxime in 19-norandrostanes?
retains activity
What is the pharm class of spironolactone based progestins?
progesterone agonist, mineralocorticoid/androgen antagonist
What agent is a spironolactone based progestin?
drospirenone
What are the benefits of drospirenone?
less weight gain/bloating, less androgenic ADR
What is the chemical class of progesterone receptor antagonist?
19-norandrostane
What agents are progesterone receptor antagonist?
mifepristone, ulipristal
What is the general structure of mifepristone?
3-ketone, 17-OH, 17-ethylene, bulky group
What is the general structure of ulipristal?
3-ketone, 17-ketone, 17-acetyl group = prodrug, bulky group
What DF do progestin only products come in?
pills, depot/IJ, implant, IUD
What DF do combo products come in?
oral, patch, vaginal ring
What DF do non-hormonal contraceptives come in?
copper IUD
What is the general structure of pregnanes for progestins?
3-ketone, C4=C5, 17-ketone
What is the general structure of 19-androstanes for progestins?
3-ketone, C4=C5, 19-H, 17-OH
What is the general structure of androstanes for progestins?
3-ketone, C4=C5, 19-methyl, 17-OH
