IS3 Exam 3 Med Chem

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Metabolism of Nilutamide occurs on the _____ and ____ groups.

nitro and methyl

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

Which group on Nilutamide are less susceptible to metabolism?

carbonyl

What is the result when methyl is substituted at position 7 on 7-oxo-DHEA derivatives?

inactive molecule

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.

Bicalutamide

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.

benozothiophene

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?

well tolerated

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?

CH3

On 5-alpha reductase inhibitors, a 7-membered A-ring is tolerated. What size ring is less potent?

5-membered A-ring

On 5-alpha reductase inhibitors, unsaturation at the 1,2 position is tolerated. On what position does unsaturation decrease potency?

5,6

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?

Testolactone

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

The SAR of aromatase requires a ______ in order to form a H-bond with His480.

3-keto group

Other than the 3-keto group, the SAR of aromatase requires what?

19-beta-methyl group

Long term use of 17-alpha-methyltestosterone can result in increased ____________.

hepatotoxicity

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?

2-alkenol

What are the active metabolites formed when Norgestimate undergoes extensive GI and hepatic metabolism?

17-deacetyl-norgestime (levonorgestrel-3-oxime) and levonorgestrel

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