Essential Organic Chemistry (Bruice)

Chapter 22

Essential Organic Chemistry (Bruice)

Chapter 22 The Organic Chemistry of Drugs: Discovery and Design
1)
What is a drug?
Answer:

A compound which interacts with a biological molecule and thereby triggers a physiological effect is called a drug.
Section: 22.0

2)
Which of the following common drugs is an antihistamine?
A)
Claritin

Norvasc

Prozac

B)

C)

D)

Trimox

E)

none of the above

Answer:

A
Section: 22.0

3)
Synthroid is used to treat underactivity of the __________.
A)
kidneys

B)

hypothalamus

Essential Organic Chemistry (Bruice)

Chapter 22

C)
liver

D)

pancreas

thyroid

E)

Answer:

E
Section: 22.0

4)
Explain the difference between a brand name and a generic name for a drug.
Answer:

The brand name means that a patent is held by a pharmaceutical company for the drug, and this drug is not available in
any other form but through this brand name until the patent expires (a patent is valid for 20 years). The generic name
means that any pharmaceutical company can market the drug under a different name.
Section: 22.1

5)
Which of the following terms is (are) synonymous with the term "proprietary name"?
A)
generic name
B)
trademark

trade name

C)

D)

brand name

E)

both C and D
Answer:

Essential Organic Chemistry (Bruice)

Chapter 22

E
Section: 22.1

6)
The __________ name of a drug is the name that any pharmaceutical company can use to identify the drug.
Answer:

generic

Section: 22.1

Essential Organic Chemistry (Bruice)

Chapter 22

7)
In pharmaceutical research, what is a "lead compound"?
Answer:

A lead compound is a pharmaceutically active compound of known structure which is used as the prototype in a search
for other, structurally similar, active compounds.
Section: 22.2

8)
In pharmaceutical research, explain what is meant by "molecular modification."
Answer:

Molecular modification is the process through which analogs of the lead compound are synthesized by altering its
structure (changing functional groups, ring sizes, chain lengths, etc).
Section: 22.2

9)
What compound served as the lead compound in the research which developed today's most commonly utilized local
anesthetics?
A)
morphine

cocaine

codeine

B)

C)

D)

sulfanilamide
E)
nitroglycerin
Answer:

B
Section: 22.3

10)

Essential Organic Chemistry (Bruice)

Chapter 22

Novocain and Xylocaine are two compounds which are commonly used as local anesthetics. The structures of these two
drugs are similar, but where Novocain has an aromatic ester functionality, Xylocaine has an aromatic amide group. Which
of these drugs has a longer lifetime in the body and why?
Answer:

Xylocaine has the longer lifetime because amides are slower to hydrolyze than esters.
Section: 22.3

11)
What compound is the most widely used analgesic for severe pain?
A)
Librium

B)

dextromethorphan
C)
Ativan

Benadryl

morphine

D)

E)

Answer:

Section: 22.3

12)
Based on the structures of morphine, codeine, and heroin, explain why heroin is the most rapid acting member of the
opiate family.
Answer:

Because heroin is less polar than morphine or codeine, it crosses the blood-brain barrier more rapidly and results in a
more rapid physiological response.
Section: 22.3

13)

Essential Organic Chemistry (Bruice)

Chapter 22

Which drug is the most widely used analgesic for severe pain?
A)
aspirin

valium

codeine

morphine

daypro

B)

C)

D)

E)

Answer:

D
Section: 22.3

14)
What is the name of the receptor in the central nervous system which binds morphine and codeine?
Answer:

the opiate receptor

Section: 22.3

15)
Why does injecting a mixture of epinephrine and Xylocaine give a more prolonged anesthetic effect than does injecting
Xylocaine alone?
Answer:

Because epinephrine is a vasoconstrictor, it reduces the blood supply to the injected area. This allows the Xylocaine to
remain in the injected area for a longer period of time.
Section: 22.3

16)
List 3 members of the opiate family, and give the main reason for their prescription by physicians.
Answer:

Essential Organic Chemistry (Bruice)

Chapter 22

morphine, codeine, dextromethorphan, etorpine, pentazocine; their major use is as pain killers or analgesics
Section: 22.3

17)
Define the term in vivo.
Answer:

in vivo means in a living organism

Section: 22.3

18)
Define bacteriostatic drug.
Answer:

This is a drug that inhibits further growth of bacteria.

Section: 22.4

19)
Who is credited with carrying out the first blind screen in his search for a "magic bullet" to cure African sleeping sickness?
A)
Jonas Salk

B)

Louis Pasteur
C)
Edward Jenner
D)
Paul Ehrlich

E)

Gerhard Domagk
Answer:

Section: 22.4

Essential Organic Chemistry (Bruice)

Chapter 22

20)
Define bactericidal drug.
Answer:

This is a drug that kills bacteria.

Section: 22.4

21)
An important part of a random screen is the recognition of effectiveness in the compounds screened. What term is used to
identify the test by which effectiveness is measured?
A)
assay

B)

dissolution

modeling

C)

D)

combinatorial analysis
E)
synergism
Answer:

Section: 22.4

Essential Organic Chemistry (Bruice)

Chapter 22

22)
What term is used to describe a screening test which is conducted outside the body, in a test tube for example?
A)
in toto

in tubo

in vitro

in loco

in vivo

B)

C)

D)

E)

Answer:

C
Section: 22.4

23)
What gave scientists the idea that azo dyes might be candidates as antibacterial agents?
Answer:

The fact that these dyes bound to wool fibers which are composed of protein led scientists to speculate that they might
also bind to bacterial proteins.
Section: 22.4

24)
Prontosil, a bright red dye, was an active antibacterial agent in vivo but not in vitro. Scientists also noted that mice given
Prontosil did not excrete a red compound. What possible explanation of the activity of Prontosil is consistent with these
two observations?
Answer:

The dye is converted into an active compound via some metabolic process of the mouse.
Section: 22.4

25)

Essential Organic Chemistry (Bruice)

Chapter 22

What term describes a drug that, once taken, inhibits further growth of bacteria?
A)
generic drug
B)
bacteriostatic drug
C)
antiviral agent
D)
vasodilation agent
E)
bactericidal drug
Answer:

B
Section: 22.4

26)
Which of the following drugs is a member of the benzodiazepine family?
A)
nitroglycerin
B)
acetylcholine
C)
morphine

penicillin

Librium

D)

E)

Answer:

Section: 22.5

Essential Organic Chemistry (Bruice)

Chapter 22

27)
Which of the following drugs, discovered serendipitiously, is known to relieve angina pectoris by dilating cardiac blood
vessels?
A)
nitroglycerin
B)
morphine

acyclovir

C)

D)

sulfanilamide
E)
Librium

Answer:

A
Section: 22.5

Essential Organic Chemistry (Bruice)

Chapter 22

28)
What term is given to the specific cellular binding site with which some drugs interact to trigger their physiological effect?
Answer:

receptor
Section: 22.6

29)
What structural feature do most effective antihistamines have in common with histamine and how is this common feature
believed to be related to the effectiveness of antihistamines as drugs?
Answer:

Like histamine, antihistamines have a protonated amino group at the end of an alkyl chain which allows these compounds
to bind to a negatively charged portion of the histamine receptor. Antihistamines thus bind to the histamine receptor and
prevent histamine from doing so.
Section: 22.6

30)
What name is given to the receptors involved in neurotransmission, memory, and wakefulness?
A)
cholinergic receptors
B)
beta-blockers
C)
histamine receptors
D)
prostaglandin receptors
E)
opiate receptors
Answer:

A
Section: 22.6

31)

Essential Organic Chemistry (Bruice)

Chapter 22

Provide the structure of histamine, and predict the most likely charge of the histamine receptor.
Answer:

Since histamine itself is positively charged, the histamine receptor is most likely negatively charged.

Section: 22.6

32)
With what other receptor does the histamine receptor show overlapping activity? Give an example.
Answer:

The histamine receptor shows overlap with the cholinergic receptor. This is why the antihistamine diphenhydramine has
been used to treat insomnia and to combat motion sickness.
Section: 22.6

33)
Which of the following drugs does not contain a heterocycle as part of its structure?
A)
Benadryl

Lipitor

Prilosec

Morphine

Librium

B)

C)

D)

E)

Answer:

Section: 22.6

Essential Organic Chemistry (Bruice)

Chapter 22

Essential Organic Chemistry (Bruice)

Chapter 22

34)
Which of the following compounds was used as a lead compound in the development of antiulcer agents?
A)
penicilloic acid
B)
cocaine

C)

heroin

D)

4-methylhistamine
E)
-lactamase
Answer:

D
Section: 22.6

35)
Explain why medical doctors should not prescribe antibiotics without proper blood test to test for bacteria in the patient.
Answer:

Since more and more bacteria have become 'drug resistant' to antibiotics then medical doctors should only prescribe an
antibiotic when a bacterial infections exists (not suspected)
Section: 22.7

36)
Name the last major class of antibiotics which were discovered. Members of this family work by inhibiting an enzyme
required for transcription in bacteria.
A)
sulfa drugs

B)

cephalasporins
C)

Essential Organic Chemistry (Bruice)

Chapter 22

tetracyclines
D)
fluoroquinolones
E)
penicillins
Answer:

D
Section: 22.7

37)
If we have a variety of effective antibiotics, why do pharmaceutical companies continue to search for new ones?
Answer:

Bacterial strains develop resistance to an antibiotic within 15 to 20 years. Drug resistant strains will only be fought with
new antibiotics or synergistic agents.
Section: 22.7

38)
What antibiotic was approved by the FDA in April 2000, to what family of organic compounds does it belong, and why
was its approval particularly important?
Answer:

Zyvox, a member of the oxazolidinone family of compounds, was approved by the FDA in April 2000. Its approval was
important because it was found to cure 75% of patients whose bacterial infections were resistant to all other antibiotics.
Section: 22.7

39)
What is the utility of molecular modeling by pharmaceutical companies?
Answer:

Molecular modeling can be use in rational drug design to screen a large number of potential drug candidates without the
huge expense of synthesis of each of these compounds. This allows one to look at interactions between the target molecule
and the potential drug by use of computational chemistry methods.
Section: 22.8

Essential Organic Chemistry (Bruice)

Chapter 22

Essential Organic Chemistry (Bruice)

Chapter 22

40)
Most antiviral drugs are analogs of __________.
A)
carbohydrates
B)
steroids

C)

nucleosides

proteins

vitamins

D)

E)

Answer:

C
Section: 22.9