4/1/2019 Oxford University Press | Online Resource Centre | Chapter 11

Patrick: An Introduction to Medicinal Chemistry 6e

Chapter 11

Results
You have answered 2 out of 15 questions correctly.
Your percentage score is 13%.
Question 1
Which of the following statements best describes pharmacodynamics?

Your answer:
a) The study of how drugs reach their target in the body and how the levels of a drug in the blood are affected by absorption, distribution,
metabolism and excretion.

Correct answer:
c) The study of how a drug interacts with its target binding site at the molecular level.
Feedback:
Pharmacokinetics is the study of how drugs reach their target in the body and how the levels of a drug in the blood are affected by
absorption, distribution, metabolism and excretion.
The study of how drugs can be designed using molecular modelling based on a drug's pharmacophore is part of a process known as
structure-based drug design.
Pharmacodynamics is the study of how a drug interacts with its target binding site at the molecular level.
Structure activity relationships are studies which are carried out to find which functional groups are important in binding a drug to its target
binding site, and hence lead to the identification of a pharmacophore.
Page reference: 153

Question 2
Which of the following statements best describes pharmacokinetics?

Your answer:
a) The study of how drugs reach their target in the body and how the levels of a drug in the blood are affected by various factors.
Feedback:
Pharmacokinetics is the study of how drugs reach their target in the body and how the levels of a drug in the blood are affected by
absorption, distribution, metabolism and excretion.
The study of how drugs can be designed using molecular modelling based on a drug's pharmacophore is part of a process known as
structure-based drug design.
Pharmacodynamics is the study of how a drug interacts with its target binding site at the molecular level.
Structure activity relationships are studies which are carried out to find which functional groups are important in binding a drug to its target
binding site, and hence lead to the identification of a pharmacophore.
Page reference: 153

Question 3
Which of the following characteristics is detrimental to oral activity?

Your answer:
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a) stability to digestive enzymes

Correct answer:
b) susceptibility to metabolic enzymes
Feedback:
If an orally administered drug is rapidly metabolised, its lifetime will be short and this will be detrimental to activity. The exceptions to the rule
are prodrugs. These are inactive compounds which are converted to active compounds by metabolic reactions.
Page reference: 153

Question 4
Which of the following is one of the rules in Lipinski's rule of five?

Your answer:
a) a molecular weight equal to 500
Correct answer:
d) a calculated logP value less than +5
Feedback:
The molecular weight should be less than 500. There should be no more than five hydrogen bond donor groups and no more than 10
hydrogen bond acceptor groups. Statement d) is correct.
Page reference: 154

Question 5
Some orally active drugs do not obey the rule of five. For example, some drugs with molecular weights greater than 500 are found to be orally
active. Which of the following mechanisms is the most likely reason for this?

Your answer:
a) transport by transport proteins
Correct answer:
c) pinocytosis
Feedback:
Some polar drugs can be transported across cell membranes by transport proteins if the drug resembles the molecule which is normally
carried by that transport protein. Small polar drugs with a molecular weight less than 200 can squeeze through the pores between the cells
lining the gut wall. Large polar molecules can be transported across cells by a process known as pinocytosis. Ion channels are not relevant
to the absorption process.
Page reference: 155

Question 6
Some orally active drugs do not obey the rule of five. For example, some highly polar drugs with a molecular weight less than 200 are found to
be orally active. Which of the following mechanisms is the most likely reason for this?

Your answer:
a) transport by transport proteins
Correct answer:
b) passage through pores between the cells of the gut wall
Feedback:
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Some polar drugs can be transported across cell membranes by transport proteins if the drug resembles the molecule which is normally
carried by that carrier protein. Small polar drugs with a molecular weight less than 200 can squeeze through the pores between the cells
lining the gut wall. Large polar molecules can be transported across cells by a process known as pinocytosis. Ion channels are not relevant
to the absorption process.
Page reference: 155

Question 7
Which type of infection could be orally treated with a highly polar antibacterial agent?

Your answer:
b) kidney infection
Correct answer:
c) gut infection
Feedback:
A highly polar antibacterial drug will not be able to cross the gut wall, since it will not be able to pass through hydrophobic cell membranes. It
will, therefore, remain in the gut and can be used to treat gut infections.
Page reference: 155

Question 8
Which of the following statements is false regarding the blood-brain barrier?

Your answer:
c) The walls of the capillaries supplying the brain are made up of several layers of cells, which act as a barrier to the release of drugs.
Feedback:
The cells making up the walls of capillaries supplying the brain are only one cell thick, but the cells are more tightly packed than those
supplying other parts of the body. As a result, drugs have to cross cell membranes to depart the blood vessels and enter the brain. There is
also a fatty coating which surrounds the blood vessels and acts as a further barrier. This fatty coating is not part of the capillary wall.
Page reference: 156-157

Question 9
Which of the following statements is the closest description of Phase I metabolism?

Your answer:
b) Reactions which occur in the blood supply.
Correct answer:
c) Reactions which add a polar functional group to a drug.
Feedback:
Option c) is the closest description.
Options b) and d) are incorrect. Some phase I metabolic reactions can occur in the blood supply or the gut wall, but they do not take place
exclusively at either of these sites. Most phase I reactions take place in the liver. Option a) describes Phase II metabolism where a polar
molecule is attached to a polar functional group already present on the drug, or placed there by phase I metabolism.
Page reference: 157-158

Question 10
Which of the following statements is the closest description of Phase II metabolism?

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Your answer:
b) Reactions which occur in the blood supply.
Correct answer:
a) Reactions which add a polar molecule to a functional group already present on a drug or one of its metabolites.
Feedback:
Option a) describes Phase II metabolism where a polar molecule is attached to a polar functional group already present on the drug, or
placed there by phase I metabolism.
Option c) describes the process of phase I metabolism.
Options b) and d) are incorrect. Some phase I metabolic reactions can occur in the blood supply or the gut wall, but they do not take place
exclusively at either of these sites. Most phase I reactions take place in the liver.
Page reference: 157-158

Question 11
Which of the following statements is not true about cytochrome P450 enzymes?

Your answer:
b) They belong to a general class of enzymes called monooxygenases.
Correct answer:
a) They contain haem and magnesium.
Feedback:
The cytochrome P450 enzymes contain haem and iron. Statements b)-d) are accurate.
Page reference:158-161

Question 12
Which of the following groups is least susceptible to cytochrome P450 enzymes?

Your answer:
b) allylic carbons
Correct answer:
d) quaternary carbon atoms
Feedback:
Exposed groups such as terminal methyl groups are susceptible to oxidation by cytochrome p450 enzymes, as are activated carbons such
as allylic and benzylic carbons. Quaternary carbon atoms are 'buried' and unlikely to be susceptible to cytochrome P450 enzymes.
Page reference: 158-161

Question 13
Alkenes and aromatic groups can be metabolised to diols. Which enzymes are involved?

Your answer:
a) cytochrome P450 enzymes
Correct answer:
c) both of the above
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Cytochrome P450 enzymes catalyse the formation of an epoxide from an aromatic ring or alkene. Epoxide hydrolase then catalyses the
hydrolysis of the epoxide to form a diol.
Page reference: 158-161

Question 14
Which of the following enzymes is not involved in catalysing a Phase I metabolic reaction?

Your answer:
b) monoamine oxidases
Correct answer:
c) glucuronyltransferase
Feedback:
Flavin-containing monooxygenases catalyse a variety of phase I oxidation reactions. Monoamine oxidase catalyses the formation of
aldehydes from primary amines. Esterases catalyse the hydrolysis of esters. All of these are phase I metabolic reactions.
Glucuronyltransferase catalyses the transfer or attachment of a sugar moiety onto a polar functional group. This is a conjugation reaction
which represents a phase II metabolic reaction.
Page reference: 158-163

Question 15
Which of the following reactions is not a Phase I metabolic transformation?

Your answer:
a) reduction of ketones
Correct answer:
b) conjugation to alcohols
Feedback:
Reactions which introduce, modify or reveal functional groups are phase I metabolic reactions. Conjugation reactions involve the attachment
of a polar molecule to a polar functional group and are phase II metabolic reactions.
The reduction of a ketone is a functional group modification (ketone to alcohol). The oxidation of an alkyl group introduces a functional group
(alcohol, ketone or carboxylic acid). Ester hydrolysis reveals functional groups (the carboxylic acid and the alcohol).
Conjugation to an alcohol is a phase II metabolic reaction.
Page reference: 158-163

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