Student name:……………………………………… Registration no……………………………….. Section no.:……………….
Philadelphia University
Department of Pharmaceutical Second semester 2012/2013
Sciences
Pharmaceutical Medicinal Chemistry-2
0510312
Final examination 5/06/2013
Lecturer: Dr. Bilal Al-Jaidi
Faculty of Pharmacy
Student name:

The exam contains 13 assay questions
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You must answer all question
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You must write your name in every page
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Wish you a good luck
Registration no.:
Question-1: choose the most appropriate answer for the following MCQs:(15 marks)
1. Regarding polyenes, the following is true:
a) They have antifungal activity
b) They inhibit ergosterol synthesis
c) As the number of double bonds increased, activity
decreased
d) A and c
2. Itraconazole is an antifungal agent, which of the following
is true regarding this drug:
a) It is one of the allylamines compounds
b) Triazole ring is important for activity
c) Triazole can be replaced by tetrazole without
affecting activity
d) It is CYP-450 inhibitor
e) All except a
3. Regarding fungal infections, the following is true:
a) Superfacial infections is treated by topical preparations
b) Systemic infections can be life-threatening
c) Cutaneous and subcutaneous are better to be treated
with combination of topical and oral agents
d) Only a and b
e) All a, b, and c are true
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4. The following facts are true regarding tuberculosis
a)
b)
c)
d)
Can affect the lungs, heart and skin
Caused by slow growing M. tuberculosis
Treatment period is short, for one month
Drugs available became insufficient for effective
treatment
e) All of the above
5. Regarding mycolic acid, the following is true:
a) Is the main cell wall component in gram +ve bacterial
b) Responsible for the M.tuberculosis protection and
virulence
c) Considered a potential target for anti-TB agents
d) Only b and c
e) All of the above
6. Regarding Pyrazinamide, the following is true:
a)
b)
c)
d)
e)
Is one of the antiviral prodrugs
The active metabolite is pyrazinoic acid
Is activated inside bacteria by catalase/peroxidase
b and c
all of the above
7. The main challenge in developing anti-fungal agents is:
a)
b)
c)
d)
8.
Nelfinavir is an anti-viral agent, which of the following is
true regarding this drug:
a)
b)
c)
d)
9.
Limited number of biological targets
The fungal cell is an eukaryotic cell
The very thick cell envelop
None of the above
Is a non-nucleoside reverse transcriptase inhibitor
Is a protease inhibitor
The group circled is not important for activity
b and c
Regarding the structure of Sulfamethoxazole, the following
is true:
a) an antibacterial agent
b) toxicity came from the reactive sulfonamide group
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c) low crystalluria because of enhanced polarity
d) inhibits dihydrofolate reductase enzyme
e) all except b
10. Regarding sparfloxacin, which of the following is true:
a)
b)
c)
d)
e)
A quinolone antibacterial agent
The carboxylic acid is not important for activity
Piperazine ring has improved acid stability
Has the lowest incidence of crystalluria formation
a and d
11. Delaviridne is an antiviral agent, which statement is true
about it:
a) Is a non-nucleoside structure
b) Is a reversible competitive inhibitor of reverse
transcriptase
c) Is an irreversible inhibitor of reverse transcriptase
d) Both a and b
e) Both a and c
12. Regarding the antiviral agent, indinavir, which of the
following is true:
a) It is a reverse transcriptase inhibitor
b) It is a viral protease inhibitor
c) The circled group makes indinavir more stable
compound toward hydrolysis.
d) It is an allosteric inhibitor
e) b and c
13. The followings is/are the challenges for developing
effective and selective antiviral agents:
a)
b)
c)
d)
many possible targets inside the viral cell
Virus depends on host cell for growth and replication
Most of them are slowly mutating cells
All of the above
14. Which of the followings is true regarding valaciclovir:
a)
b)
c)
d)
e)
Is a prodrug
Ester hydrolysis will release the active drug
Less toxic than acyclovir
Is a nucleoside DNA polymerases inhibitor
Only a and b
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15. Regarding acyclovir triphosphate, the following is true:
a) Is the active form of acyclovir
b) Should be dephosphorylated by kinase to give the
active form of the drug.
c) Inhibits viral protease
d) Is selective on virus, does not affect mammalian cell.
e) a and d
16. Regarding drug protein binding, the following is not true:
a)
b)
c)
d)
e)
The fraction of drug bounded will be tissue not available.
The fraction of drug bounded will not be excreted in urine.
May result in drug accumulation in the body.
No role for the chemical structure of the drug in the protein binding.
None of the above.
17. Regarding Mustine, the following is true:
a) It acts as an alkylating agent
b) The nitrogen might play a role in the mechanism of
action
c) No role for the chlorine atom in activity
d) a and b
e) All of the above
18. Regarding Treosulfon, the following is true:
a)
b)
c)
d)
The sulfonate group is important for activity
The removal of OH group will abolish the activity
The selected carbon is the reactive part in the structure
All of the above
19. Regarding the structure of Melphalan, the following is true:
a)
b)
c)
d)
The circled group is the alkylating group
It will reversibly bind to DNA
Its polarity behinds its better distribution
b and c
20. Carmustine is an anticancer agent, which of the following is
true regarding this drug:
a) Used in brain tumour because it has the reactive
nitroso group
b) The dichloroethyl group is responsible for the
alkylating activity
c) It can only form one covalent bond with DNA
d) Only a and b
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e) All of the above
21. Regarding M. tuberculosis, the following is true:
a)
b)
c)
d)
e)
It can persist inside macrophages
Synthesize mycolic acid using both FAS-I and FAS-II systems
A slow growing, highly resistant baceteria
Only a and b
All of the above
22. The following is true regarding bacterial resistance except:
a)
b)
c)
d)
Efflux pump is resistant mechanism
XDR-TB is resistant to at least isoniazid and Rifampicin
Isoniazid resistant is due to mutation in gyrase enzyme
Resistance to sulfonamide is due to the production of
destroying enzyme
e) a and b
23. Regarding HIV-Protease inhibitors, the following is true:
a)
b)
c)
d)
e)
They are oligopeptides in structure
They have pharmacokinetic problems
Specifically have proline-ala bonds
Biologically highly Stable compounds
Only a and b
24. Regarding the SAR for quinolones, the following is true:
a)
b)
c)
d)
e)
Position-2 can be substituted with small methyl group
The β-keto acid has no role in metal Chelation
Position 7 and 8 can be ring annulated
N8 cannot be replaced with carbon atom
c and d
25. Regarding prontosil, the following is true:
a)
b)
c)
d)
e)
active in-vitro
Sulphanilamide is its active metabolite
sulfonamide hydrolysis will give its active form
a and b
e. all of the above
26. Regarding Cefdinir, the following is true:
A. It has good oral availability (> 70%)
B. Acid stable agent
C. The circled group has no role in binding to the enzyme
active site
D. Highly lipophilic structure
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E. Only A and B
Question-2: Answer the next questions regarding the following two compounds: (4 marks)
1. What are the possible pharmacological action of these agents; are they antiviral,
antibacterial, anticancer agents, explain your answer?
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2. Which one do you think is a prodrug, and why?
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Question-3: (3 marks)
Chlorambucil is an anti-cancer agent, answer the following questions based on its structure below:
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1. It is an alkylating agent; explain how it will alkylate DNA?
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2. Is there any role for the carboxylic acid group? Discuss your answer?
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Question-4: (2 marks)
Sulfonamides and quinolones are antibacterial agents, both have the possibility to form crystals in
urine BUT with completely different mechanisms, explain?
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Question-5: (2 marks)
Estramustine is an alkylating anticancer agent with better selectivity on cancer cells than other
alkylating agents, describe the most important parts in its structure?
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Question-6: study carefully the following drug structures and answer the questions that follow:(10
marks)
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1. Compound.............. is the drug of choice for nail fungal infections.
2. Compound .......... and ............. can be antiviral agents
3. Compound H is an anticancer agent because.............................................................................
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4. Compound E exists as a racemate, the most active isomer is the ............................ isomer
5. Compound ........................... is called Fluconazole
6. The N3 group in compound C is important for its action because...............................................
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7. Compound .................................... is Azole antifungal agent, while Compound .................... is
a Nucleoside-reverse transcriptase inhibitor.
8. Compound ......... is a peptidomimetic agent, having (anticancer or antiviral activity).
9. Draw the mechanism of activation for Compound C:..................................................................
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Question-7: (2 marks)
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Student name:……………………………………… Registration no……………………………….. Section no.:……………….
Describe how does Cisplatin inhibit the DNA transcription and replication (include a suitable drawing
to support your answer)?
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