Metabolism Pre-Test

Prof. Patrick J. Davis

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This "Metabolism Pre-Test" does not rely on any knowledge of drug metabolism. Rather, it relies on various basic chemical principles (including those reviewed by Dr. Kerwin) that we will rely on for the metabolism section of this course. I have intentionally avoided the inclusion of any structures under the assumption that you will draw them out in order to answer the questions (you need to get into the habit of doing this!). Answer the questions below and then click "submit" to send your answers. You will be sent an EMail with the corrected quiz within seconds to the address you specify.

You will learn that "esterases" are enzymes that hydrolyze esters, and thus yield the same products that you would get from acid- or base-catalyzed hydrolysis of esters. Therefore, a drug molecule containing an ester functional group that is hydrolyzed by an esterase would yield:

Your answer:
an aldehyde (RCHO) and an alcohol (R'OH).
an acid (RCOOH) and an alkane (R'CH3).
an acid (RCOOH) and an alcohol (R'OH).
two alcohols (ROH and R'OH).
an acid (RCOOH) and an aldehyde (R'CHO).

You will learn that "amidases" are enzymes that hydrolyze amides. Therefore, the hydrolysis of a drug molecule containing an amide functional group by an amidase would yield:

Your answer:
an acid and an alcohol.
an amine and an aldehyde
an amine and an alcohol.
an amine and an alkane.
an amine and an acid.

You will learn that cytochrome P-450 is capable of converting benzene to phenol. The proper way to characterize this reaction would be that:

Your answer:
it represents a reaction involving stereochemistry.
it represents a reduction reaction.
such a reaction is simply not possible.
it represents a hydrolytic reaction (hydrolysis).
it represents a hydroxylation reaction.

You will learn that primary alcohols are typcially oxidized to aldehydes (by alcohol dehydrogenase) and the resulting aldehyde is then oxidized to an acid (by aldehyde dehydrogenase). From this, you would predict that ethanol would be converted to:

Your answer:
acetaldehyde and then to acetic acid.
nothing. This set of enzymatic reactions is simply not possible with ethanol.
acetaldehyde and then stop (the second oxidation is not possible).
acetaldehyde and then to acetone.
acetic acid directly (no intermediate acetaldehyde).

You will learn that primary alcohols are typcially oxidized to aldehydes (by alcohol dehydrogenase) and the resulting aldehyde is then oxidized to an acid (by aldehyde dehydrogenase). From this, you would predict that phenol would be converted to:

Your answer:
benzoic acid directly (no intermediate benzaldehyde).
nothing. This set of enzymatic reactions is simply not possible with phenol.
benzaldehyde and then to benzoic acid.
benzaldehyde and then to acetophenone.
benzaldehyde and then stop (the second oxidation is impossible).

You will learn that amines are converted to amine oxides by cytochrome P-450 and amine oxidases. However, it is typically only tertiary amines that are converted to amine oxides. From this, which one fo the following compounds is MOST likely to be converted to an amine oxide metabolically?

Your answer:
N,N-Dimethylaniline
Aniline
N-Methylaniline
Trimethylanilinium chloride
None of the four compounds listed would be converted to an amine oxide.

You will learn that amines are converted to amine oxides as described in the previous question. You will also learn that, since this process requires the availability of the lone pair of electrons on the nitrogen, the more BASIC the amine, the more likely an N-oxide will form. From this, which ONE of the following compunds is most likely to be converted to an amine oxide metabolically?

Your answer:
N,N-Dimethylaniline
Aniline
N-Methyl-N-acetylaniline
N,N-Dimethyl-N-benzylamine
Urea

You will learn that keto-reductases are enzymes that have the capability of reducing ketones to alcohols. Based on this, which ONE of the following statements concerning acetophenone (phenylmethylketone) is INCORRECT?

Your answer:
Acetophenone could be reduced to a racemic alcohol.
Acetophenone could be reduced to a primary alcohol.
Acetophenone could be reduced to a secondary alcohol.
Acetophenone could be reduced to an S-alcohol.
Acetophenone could be reduced to an R-alcohol.

You will learn that keto-reductases are enzymes that have the capability of reducing ketones to alcohols. Based on this, which ONE of the following statements concerning acetone is CORRECT?

Your answer:
Acetone could be reduced to an R-alcohol.
Acetone could be reduced to a secondary alcohol.
Acetone could be reduced to a primary alcohol.
Acetone could be reduced to an S-alcohol.
Acetone could be reduced to a racemic alcohol.

You will learn that aromatic hydroxylation reactions catalyzed by cytochrome P-450 follow the well-established rules of electrophicl aromatic substitution. Based on this, which ONE of the following statements most logically predicts the outcome of cytochrome P-450 mediated hydroxylation of anisole (methoxybenene).

Your answer:
meta-hydroxylation only.
ortho, and/or meta, and/or para-hydroxylation.
ortho-hydroxylation only.
para-hydroxlation only.
ortho and/or para hydroxylation.

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