IS3 Exam 3 Med Chem
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Created by:
epalmer1228 on April 16, 2012
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25 terms
Terms | Definitions |
|---|---|
 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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