Cairo University

Faculty of Pharmacy

Pharmaceutical Chemistry Department Model answer

Final written exam for level four

First semester, 2023-2024
Medicinal Chemistry 2
Course Code: PC711
11 February 2024 Time allowed: 3 hours Total marks: 100 marks

N.B. The oral exam will be directly after the written exam at room J110 in
Building J.

Q-I) Choose the correct answer and put it in the provided answer sheet [95
Marks].
N.B. Only answers in the answer sheet will be considered, therefore, put your
answer in the provided answer sheet.
1- The active metabolite of Diltiazem

2- The most important role of the encircled moiety of

Amlodipine
a) It increases selectivity for the vascular smooth muscle than
myocardial tissue.
b) It Increases metabolic rate and the compound excreted in the bile.
c) It enhances the photolability of the compound.
d) It enhances the photostability of the compound.

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3- From structure activity relationship of 1,4-Dihydropyridines:
1- 1,4-Dihydropyridine ring (DHP) with secondary cyclic amine are essential.
2- Positions 3 and 5 are carboxylic groups that must be protected with an ester functional
group.
3- Position 4 requires an aromatic substitution possessing an electron-donating group in
the ortho and/or meta position.
4- Positions 2 and 6 small alkyl group, that may play a role in the duration of action.
a) All of them b) All except 3 c) All except 1 d) 1 &2

4- The metabolite which has approximately 15 times more

potent than the parent compound of Losartan.

5- The important binding points at the active site of ACE are:

1- An arginine residue, which provides a cationic site that attracts a carboxylate ion.
2- A zinc ion which binds with thiol group.
3- Hydrophobic pockets lie between these groups in the active site.
4- A Functional group that forms a hydrogen bond with an amide carbonyl.
a) All of them b) All except 3 c) All except 1 d) 1 &2

6- The major metabolite of Nifedipine

a) b) c)
7- The active metabolite of Propranolol is
a) 4-Hydroxypropranolol.
b) Naphthoxylactic acid.
c) N-dealkylated derivative.
d) None of them.

8- The most important role of encircled moiety of Mexiletine

a) It increases lipophilicity.
b) It enhances rate of metabolism.
c) It increases the stability of the compound where it is not subject to the hydrolysis
common to the amide lidocaine.
d) All of them.

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 9- From SAR of Beta blockers,
1- Most of β-blockers are in the chemical class of aryloxypropanolamines
2- For maximal β –blockers: the β -OH-substituted carbon must be in the R absolute
3- The aromatic ring can either be benzoheterocyclic (such as indole) or heterocyclic (such as
thiadiazole).
4- The X part of the side chain can either be CH2CH2—, —CH=CH—, —SCH2— or —NCH2
5- Branched R1 group is the optimal for activity
6- Alkyl (—CH3) substituents on the α, β or γ carbon (if X = —OCH2—) enhances beta
blockade, especially at the α carbon
a) 1 &4 & 5 b) 1 &3 & 6 c) 2 &3 & 5 d) 1 &3 & 5

10- The role of the encircled moiety

a) It increases lipophilicity that results in improvement of
bioavailability up to 90 % compared to the 55 % of prazosin.
b) Increasing metabolic rate and the compound excreted in the bile.
c) It enhances the activity, where the compound has a 5,000-fold greater affinity for α 1-
receptors than for some α 2-adrenergic receptors.
d) It decreases the metabolic rate and the metabolites excreted in the bile.

11- Considering Isoflurophate, which of the following statements is True?

a) It is considered a reversible direct-acting cholinergic agonist.
b) It is considered an irreversible direct-acting cholinergic agonist.
c) It is considered a reversible indirect-acting cholinergic agonist.
d) It is considered an irreversible indirect-acting cholinergic agonist.

12- …………….. is the reagent used for the synthesis of Ethopropazine.

H3C H3C H3C H3C
H3C H3C
a) N b) N
c) N
d) N
CH3 CH3 Cl CH3 Cl CH3
Cl Cl
CH3 CH3

13- Chemical name of Neostigmine bromide

a) (m-Hydroxyphenyl)trimethylammonium bromide, dimethyl carbamate O N(CH3)2
b) (p-Hydroxyphenyl)trimethylammonium bromide, methyl carbamate
O
c) (m-Hydroxyphenyl)triethylammonium bromide, methyl carbamate
d) (p-Hydroxyphenyl)triethylammonium bromide, ethyl carbamate N+(CH3)3 Br-

14- Glycopyrrolate is ……………

i-Phenothiazine derivative
ii-Synthetic amino alcohols esters
iii-Synthetic amino ethers
iv-Useful in treatment of Parkinsonism
v-Useful in treatment of hyper-motility and spasm
a) i,iv b) ii,v c) iii,iv d) i,v

15- Metyrosine …………..

a) Prevents the release of norepinephrine.
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b) Is affecting norepinephrine biosynthesis.
c) Is a dopamine and noradrenaline reuptake inhibitor.
d) Is an inhibitor of aromatic L-amino acid decarboxylase.

16- Substitution on α-carbon to phenylethanolamine adrenergic agonists introduces

another asymmetric center. When phenyl ring has no substitution, these may have
both direct and indirect activity.
a) Ephedrine (1S, 2R) stereoisomer has mixed direct and indirect activity.
b) Ephedrine (1S, 2R) stereoisomer has only direct activity.
c) Ephedrine (1R, 2S) stereoisomer has mixed direct and indirect activity.
d) Ephedrine (1R, 2S) stereoisomer has only direct activity.

17- Which of the following is selective α1 antagonist selectively bind to receptors in the
prostate aiding to the treatment of BPH?
a) Prazosin. b) Tamsulosin. c) Salbutamol. d) Mirabegron.

18- Salbutamol is an important clinical agent. What role does the t-butyl group play?
a) It acts as steric shield to reduce metabolism.
b) It increases hydrophobicity such that the molecule can cross cell membranes.
c) It introduces selectivity for β-adrenoceptors.
d) It introduces selectivity for α-adrenoceptors.

19- Considering Diethylpropoin, which of the following statements is True

a) Structurally related to cathinone.
b) Higher cardiovascular effects compared to amphetamine.
c) Higher sympathomimetics effects compared to amphetamine.
d) Higher CNS stimulatory effects compared to amphetamine.

20- Considering analeptics, which of the following statements is False

a) Potent and selective CNS stimulants.
b) Their convulsive dose lies near their analeptic dose.
c) Excite the vasomotor and respiratory centers of the medulla.
d) Used for post-anesthetic respiratory depression.

21- Which of the following structural components of Desipramine makes it more

selective for NET and less selective for SERT
a) The 6-7-6 tricyclic ring system. b) Branching of the side chain.
c) Chlorine substituent on the ring system. d) All answers are false.
CF3

22- Chemical name of Fluoxetine

a) 3-Phenyl-3-(4-trifluoromethylphenoxy)-N-ethylbutylamine
b) 3-Phenyl-3-(4-trifluoroethylphenoxy)-N-methylethylamine O

c) 3-Phenyl-3-(4-trifluoromethylphenoxy)-N-methylpropylamine
d) 3-Phenoxy-3-(4-trifluoroethylphenyl)-N-ethylpropylamine N
H3C H

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23- Which of the following is true for MAOIs
a) They can lead to hypotensive reactions.
b) They can decrease the degradation of dietary tyramine.
c) They reversibly inhibit monoamines reuptake.
d) They irreversibly inhibit monoamines reuptake.
24- o-Quinonoid is a reactive metabolite of ……………
a) Fluoxetine. b) Trazodone. c) Paroxetine. d) Atomoxetine.

25- …………….. is the intermediate produced during the synthesis of Bupropion.

O O O O
a) b) Cl c) d) Cl
CH3 CH3
Cl Cl CH3 CH3

26- All the followings are correct about zopiclone EXCEPT:

Cl
a) It is a cyclopyrrolone derivative. O

b) Its S-isomer is active as hypnotic and has no withdrawal N

N N
symptoms.
O
c) It is a superagonist at the benzodiazepine binding site at N
N N CH3
GABAA receptor. O

d) It has short duration of action.

27- Chlordiazepoxide can be metabolized to give active

metabolites by all the following EXCEPT:
a) N-demethylation.
b) Oxidative deamination.
c) N-alkylation.
d) None of the above.

28- The following can be arranged according to their potency:

a) A > B > C. b) A > C > B.

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c) C > B > A. d) C > A > B.

29- All the following are correct about Tofisopam EXCEPT:

a) It binds to the benzodiazepine binding site of the GABA
receptor.
b) It is an atypical anxiolytic drug.
c) It has no anticonvulsant activity.
d) Its D enantiomer is used for the treatment of irritable bowel
syndrome.

30- The following structures can be arranged according to their potency as skeletal
muscle relaxants:

a) B > C > A. b) A > B > C.

c) C > B > A. d) C > A> B.

31- Pregabalin:
a) Increases the expression of glutamic acid decarboxylase
which is responsible for GABA synthesis.
b) Its S- isomer is an active enantiomer.
c) Blocks presynaptic voltage-gated Ca2+ channels.
d) All the above.

32- Which of the following has the highest potency as an antipsychotic:

33- The following inhalation anesthetics can be arranged according to their potency:

a) B > C > D > A. b) A > B > C > D.

c) B > A > C > D. d) C > B > A > D.

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34- Levodopa should be taken with carbidopa in Parkinson`s disease because:
a) Carbidopa is a peripheral DOPA decarboxylase inhibitor.
b) Carbidopa ensures high delivery of L-DOPA to CNS.
c) Carpidopa decreases amount of formed Dopamine peripherally decreasing its side
effects.
d) All of the above.

35- All the following are true about Tolcapone EXCEPT:

a) It inhibits COMT peripherally and centrally.
b) It lacks hepatotoxicity.
c) It causes hepatotoxicity.
d) It is indicated with levodopa and carbidopa.
36- The chemical name of Methyprylon is:
a) 3,3-Diethyl-5-methyl-2,4-piperidine dione.
b) 5,5-Diethyl-3-methyl-4,6-piperidine dione.
c) 2,2-Diethyl-4-methylglutarimide.
d) 2,2-Diethyl-6-methylglutarimide.

37- All the following are correct about haloperidol EXCEPT:

a) It is one of the typical antipsychotic drugs.
F OH
b) It is a strong D2 antagonist. N
c) It has anticholinergic side effects. O

d) Its decanoate ester was used as an intramuscular depot. Cl

38- 3-Propofol is an intravenous General anesthesia characterized by:

a) Rapid onset of action.
b) Long duration of action.
c) induction of nausea and emesis.
d) All the above.

39- Memantine manages Alzheimer`s disease through:

a) inhibition of cholinesterase.
b) regulating the activity of glutamate in brain.
c) inhibition of beta amyloid plaques formation.
d) All the above.

40- ………………….. is used for its nootropic effect.

a) Hydroxyzine. b) Meclizine.
c) Cinnarizine. d) Cetirizine.

41- Which of the following H1 antagonists could be used in the treatment of

Parkinsonism?

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 (a) (b) (c) (d)

42- Which is true concerning the following two H1 antagonists?

Compound A Compound B
a) Compound A is more potent and causes less sedation than compound B.
b) Compound A is less potent and causes more sedation than compound B.
c) Compound A is more potent and causes more sedation than compound B.
d) Compound A is less potent and causes less sedation than compound B.

43- Which is true concerning the following drug?

a) It is a reversible direct inhibitor of proton pump
b) It is a prodrug that is converted to a sulfonamide intermediate.
c) It has a short duration due to the presence of 5-methylpyridine
d) Its S isomer binds more efficiently to the pump.

44- The following compound has the following disadvantage(s):

a) poor oral bioavailability.
b) present mainly in the nonpharmacophoric Nπ-H tautomer.
c) both a and b.
d) None of the above.

45- Nizatidine does not cause enzyme inhibition as Cimetidine due to

a( changing of the imidazole ring by a thiazole ring.

b( changing the cyanoguanidine group by N-methyl-2-nitro-1,1-ethenediamine group.
c( adding dimethylaminomethyl side chain to the ring.
d( all of the above.

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46- The active form of pantoprazole is

47- Which of the following statements is correct concerning tolycaine?

a) It is an ester local anesthetic.
b) Its main side effect is rash.
c) It is metabolized mainly by amide hydrolysis.
d) It produces decreased CNS side effects compared to lidocaine.

48- Which of the following structures will be inactive as a local anesthetic?

a) b) c) d)

49- Which of the following regions is not involved in local anesthetics receptor
interaction?

a) Region A. b) Region B.
c) Region C. d) Region D.

50- ........................... is centrally and peripherally acting antitussive and structurally

related to a local anesthetic.

a) b)

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 c) d)

51- Formoterol is a long acting bronchodilator and group ................

is responsible for the β2 selectivity.
a) Phenylethylamine. b) N-isopropyl-p-methoxyphenyl group.
c) formamide group. d) a and c.

52- ....................has/ have a good action against COVID-19

a) b)

c)

d) a & c
53- Glibizide has longer duration of action than tolazamide due to presence of
............ moiety
a) Sulfonylurea.
b) Cyclohexyl.
c) substituted arylcaboxyamidoethyl.
d) All of the above.

54- Presence of p-chloro substituent in

bexagliflozin was led
to............................................
a) an increase in drug potency.
b) a decrease in drug potency.
c) removing of antidiabetic activity.
d) None of the above.

55- All the following are right about tirzepatide except

that, ....................
a) it is a GIP-analogue.
b) it activates only GIP- receptor.
c) it has been chemically modified by lipidation to improve
its uptake into cells and its stability to metabolism.
d) it activates both the GLP-1 and GIP receptors.

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56- ........................................in saxagliptin form a covalent
bond with serine 630 OH in the enzyme catalytic residue of
DPP-4 enzyme.
a) Adamantyl group. b) CN group.
c) Amide group. d) Amide and CN groups.

57- The illustrated chemical structure belongs to which class?

a) Thiazides.
b) Carbonic anhydrase inhibitors.
c) Osmotic diuretics.
d) None of them.

58- Hyperkalemia can take place due to the use of

a) b)

c) d) None of them.

59- Alteration of which position can increase the

duration of action in the illustrated figure?
a) position 3. b) position 4.
c) position 5. d) position 7.

60- A diuretic which is a m-sulfamoyl benzoic acid derivative

a) Torsemide. b) Xipamide. c) Bumetanide. d) None of them.

61- The compound shown in the figure is the active

metabolite of:
a) Bulk laxative. b) Stimulant laxative.
c) osmotic laxative. d) None of them.

62- The drug shown in the figure has no CNS opioid effects
due to
a) it does not cross BBB.
b) its polarity.
c) its lipophilicity.
d) none of these.

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63- The illustrated drug has the following action
a) Antiemetic.
b) Antidiarrheal.
c) Antiulcer.
d) None of them.

64- All of the following are correct about this drug except:
a) it is an antiplatelet agent.
b) it is a phosphodiesterase inhibitor.
c) it decreases the intraplatelet cAMP.
d) it is used in combination with aspirin.

65- Dobutamine is a positive inotropic agent via

a) inhibiting phosphodiesterase III.
b) being β1-adrenergic receptor agonist.
c) acting as a calcium sensitizer. d) inhibiting the Na+/K+ ATPase.

66- One of the advantages of LMWH is…………..

a) increasing incidence of heparin-induced thrombocytopenia.
b) need monitoring of its anticoagulation effect.
c) binding more to plasma proteins.
d) resistance to inhibition by activated platelets.

67- ……………. is cholesterol absorption inhibitor.

a) Cholestyramine resin. b) Ezetimibe.
c) Gemfibrozil. d) Acipimox.

68- In the following cardiotonic agent, presence of the encircled moiety making
it.………..
a) β1-adrenergic receptor agonist.
b) phosphodiesterase III activator.
c) phosphodiesterase III inhibitor.
d) β1-adrenergic receptor antagonist.

69- Which of the following is true about clopidogrel?

a) ADP receptors agonist prodrug and the S-isomer is the active one.
b) ADP receptors antagonist prodrug and the R-isomer is the active one.
c) ADP receptors agonist prodrug and the R-isomer is the active one.
d) ADP receptors antagonist prodrug and the S-isomer is the active one.

70- Fibrates activate peroxisome proliferator-activated receptors that leads to

a) increasing HDL level. b) decreasing VLDL catabolism.
c) increasing VLDL level. d) decreasing HDL level.

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 71- ……….. …..…………… resulted in scurvy
a) Deficiency of vitamin B6. b) Hypervitaminosis of vitamin A.
c) Hypervitaminosis of vitamin K. d) Deficiency of vitamin C.

72- Vitamin A can be determined quantitatively using…………..

a) Carr-Price method. b) standard sodium hydroxide.
c) cerium (IV) ammonium sulfate. d) fluorometric method.

73- According to the structure-activity relationship of the

following compound,
a) if R is COOH, it will be inactive.
b) if R is CHO, it will be inactive.
c) if R is COOH, it will be active.
d) if R is CH2OH, it will be inactive.

74- All the following is true about vitamin E, EXCEPT

a) They’re derivatives of 2, 3-benzopyran.
b) Ethers of tocopherols are active.
c) Called the Anti-Sterility Factor.
d) Antioxidants.

75- Vitamin K is used for the treatment of ……..

a) hyperlipidemia. b) hyperparathyroidism.
c) hypoprothrombinemia. d) hypochromic anemia.

76- ……………. is a vitamin D analog that is used for hypoparathyroidism.

a) Etretinate. b) Dihydrotachysterol.
c) Tazarotene. d) Calcifediol.

Q-II) Answer the following (5 marks):

A-Complete the synthetic pathway of carbamazepine: (3 marks)

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B- Draw 2 metabolites of Diazepam, one is active and the other one is inactive: (2
marks)

Diazepam Active metabolite inactive metabolite

End of questions
Good luck
Prof. Dr. Ramzia ElBagary
Prof. Dr. Doaa Ezzat
Prof. Dr. Riham F. George
Dr. Samar Hashem
Dr. Mona Fikry
Dr. Ghada Elmasry
Dr. Menna-Allah Mohamed
Dr. Noha Mohamed

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