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What is the result of Nilutamide metabolism on the nitro group? on the methyl group?
1. nitro group=formation of reactive NO and oxygen species that facilitate toxic effects
2. methyl group= D-isomers are formed are active metabolites
What is the result when methyl is substituted at position 7 on 7-oxo-DHEA derivatives?
Exemestane is a _____ generation _______ inhibitor used to treat excess amounts of estrogens.
third generation, aromatase
Exemestane is a ________ inactivator that ______ binds to the substrate binding site. This drug causes levels of aromatase to ______.
steroidal, irreversibly, decrease
This androgen receptor inhibitor is used as a racemic mix, but the active androgen inhibitor is the R-isomer.
Raloxifene is a SERM that is derived from _______ and can be used to decrease osteoporosis in post-menopausal women and as a breast cancer treatment.
5-alpha-reductase inhibitors can be used in the treatment of excess _____________. What type of 5-alpha reductase do they inhibit?
androgens, type 2
On 5-alpha-reductase inhibitors, a substitution with a 16-methyl or a 7-beta substitution are both?
On 5-alpha reductase inhibitors, there is usually a 3-keto group. What substitutions are not well tolerated at this position?
S, CH2, CH3N, HON
On 5-alpha reductase inhibitors, there is a 4-aza group. A hydrogen or small hydrophobic group is preferred. What other group (R1) can increase androgen receptor affinity?
On 5-alpha reductase inhibitors, a 7-membered A-ring is tolerated. What size ring is less potent?
On 5-alpha reductase inhibitors, unsaturation at the 1,2 position is tolerated. On what position does unsaturation decrease potency?
On 5-alpha reductase inhibitors, what R2 group is preferred at position 17?
lipophilic amides or ketones
What first generation aromatase inhibitor has a lactone ring in place of the 5-membered D-ring?
Nandrolone drugs are used as esters. How does the length of the ester chain affect onset and half-life?
longer the ester=slower onset and longer half-life
What prevents 17-beta-hydroxyl metabolism on 17-alpha-methyltestosterone?
The 17-alkyl group, which is methyl (any groups larger than methyl will decrease activity)
Steroidal hormones such as testosterone undeconate and testosterone enanthate have a 17-beta-hydroxyl group that has been esterified. What is the result of this esterification?
increased lipophilicity and increased duration of action of testosterone
Delestrogen is an estradiol derivative with a _______ that allows for slow absorption and prolonged duration of action.
17-ester (the 17-ester group is valerate, which is an alkyl ester group)
Oxymetholone is an anabolic derivative of testosterone. What substitution on this molecule increases anabolic activity?
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