Dr.

Fatima Arain

Medicinal Chemistry

PHARMACY PREP.
MEDICAL CHEMESTRY
1- Glycine may undergoes conjugation with:
a) Carboxylic acid
b) Gluthatione conjugates
c) Cytochrome P450
d) Sulfonamides conjugates
e) Amides conjugates
2- Pyrrolidine and piperidine are important heterocyclic compounds in the
structure of drugs. Which of the following drugs has these heterocyclic rings
on its structure?
a) Folic acid
b) Clonidine
c) Tetrodotoxin
d) Imipramim
e) Atropine
3- Vinyl is a common group in the molecular structure of drugs. Which of
the following groups is commonly called a vinyl group?
a) H2C=CH
b) H3CO
c) H2C=CHCH2
d) H3CC
e) HCC
4- Tetracycline is an important group of anti-infective agents that suffer in
vivo an important metabolism reaction. The transfer of tetracycline to epitetracycline is called:
a) Isomerization
b) Oxidation
c) Polymerization
d) Racemization
e) Epimerization

Dr.Fatima Arain

Medicinal Chemistry

5- Alkyl group that mostly undergoes oxidation to an acid is known as:

a) Terminal
b) Aromatic
c) Benzylic
d) Heterocyclic
e) Cyclic

6- Amines are one of the most common group present in the molecular
structure of drugs. Primary amines are mainly metabolized by:
a) Deamination
b) Dealkylation
c) Acetylation
d) Hydrolysis
e) Oxidation
7- Compound considered an isomer of hexane include:
a) Cyclohexane
b) Cyclopentane
c) 1-methyl-pentane
d) 1-methyl-cyclohexane
e) None of the above
8- Structure activity studies of cholinergic drugs indicate that:
I- Maximum activity is achieved when the quaternary nitrogen is three
carbons removed from the ester group
II- Structures which display a quasi-ring conformation exhibit muscarinic
activity
III- One methyl group of the trimethylammonium group can be replaced by
an ethyl group with only slight loss of activity.
a) I only
b) III only
c) I and II only
d) II and III only
e) All are correct
9- Carboxylic acids are one of the most common groups present in the
molecular structure of drugs mainly metabolized by:
a) Oxidation

Dr.Fatima Arain

Medicinal Chemistry

b) Hydrolysis
c) Conjugation
d) Estherification
e) Deamination
10- For an antihistaminic drug be effective, it must have which of the
following molecular characteristics on its structure?
I- A terminal tertiary nitrogen
II- More than one aryl or heretoaryl group
III- Presence of CCC between CO
a) I only
b) III only
c) I and II only
d) II and III only
e) All are correct

11- Arrange the following groups from the most reactive to the least
reactive:
COOH CH4 OCH3 COO
a) COOCOOHOCH3CH4
b) COOHCH4 COOOCH3
c) OCH3 COOHCOOCH4
d) CH4OCH3COOCOOH
e) COOHOCH3CH4 COO
12- Isomerism are compounds that have the same molecular formula but
different chemical structures, and may be classified in many different ways
depending of structure. One example is conformational isomerism that is
characterized by:
I- The relationship between isomers that differ only by rotations around
single bond
II- The molecules must be stereoisomers
III- They can be enantiomers
a) I only
b) III only
c) I and II only
d) II and III only

Dr.Fatima Arain

Medicinal Chemistry

e) All are correct

13- Optic isomerism may be classified in CIS and TRAS, which of the
following is an example of optic isomerism?
a) Butene
b) 1-Butene
c) 2-Butene
d) 3-Butyne
e) 1-Butane
14- Conformation of the 2-methyl groups in 1,4-dimethyl-cyclohexane is:
a) Equatorial-equatorial
b) Conformational-conformational
c) Equatorial-spatial
d) Geometric-geometric
e) Spatial-spatial
15- Choracetic acid is stronger than acetic acid due to:
a) Higher ionization effect
b) Higher molecular weight
c) Higher disintegration rate
d) Electron withdrawal effect
e) All are right

16- Pyridine is a monocyclic heterocyclic compound very important in the

activity of many different drugs. The molecular structure 1,4dihydropyridine is found in:
a) Verapamil
b) Digoxin
c) Clonidine
d) Nifedipine
e) Diltiazen
17- Quinolone structure may be found in which of the following substances?
a) Vitamin K
b) Thiamine
c) Cyanocobalamin
d) Folic acid
e) Vitamin A

Dr.Fatima Arain

Medicinal Chemistry

18- Arrange the following pKa according to their acidity, from the least acid
to the strong acid. pKa 3.0, 5.2, 6.0, 2.0
a) 6.0 5.2 2.0 3.0
b) 5.23.0 2.0 6.0
c) 6.0 3.0 2.0 5.2
d) 2.0 3.0 5.2 6.0
e) 6.0 5.2 3.0 2.0

19- How many cyclohexane and cyclopentane respectively has a steroid

compound?
a) 2 and 3
b) 3 and 2
c) 4 and 1
d) 3 and 1
e) 1 and 3

20- Drugs containing hydroxyl group or carboxyl group is best metabolized

by:
a) Acetylation
b) Glucuronidation
c) Reduction
d) Hydrolysis
e) Methylation
21- Which of the following is the strongest acid?
a) Acetic acid
b) Hydrochloric acid
c) Chloracetic acid
d) Benzylic acid
e) Carboxylic acid
22- Which of the following functional group is more susceptible to
hydrolysis?
a) R-COO-R
b) R-O-R
c) R-NHCH3
d) R-COOH

Dr.Fatima Arain

Medicinal Chemistry

e) R-CH=O

23- Phenol is a weak acid due to:

a) Stable cation resonance
b) Weak dissociation
c) Common ion effect
d) Stable anion resonance
e) Fast dissociation is lipophilic solutions
24- Arrange the following groups according with their solubility, from the
most water soluble to the least water soluble:
COOH CH4 OCH3 COO
a) COOHOCH3CH4 COO
b) COOHCH4 COOOCH3
c) OCH3 COOHCOOCH4
d) CH4OCH3COOCOOH
e) COOCOOHOCH3CH4
25- Wrong statement regarding optical isomerism include:
a) Known as chiral
b) Have diastomers to its mirror image
c) Rotation of polarized light
d) Has at least one asymmetric carbon atom
e) Has one or more chiral center
26- R-COOH is an acid while R-OH is not due to:
a) Presence of dipole
b) Presence of stable anionic resonance
c) Presence of stable cationic resonance

Dr.Fatima Arain

Medicinal Chemistry

d) Presence of stable non-ionic resonance

e) Complexation
27- The pH value is calculated mathematically as the:
a) Log of the hydroxyl ion (OH ) concentration
b) Negative log of the OH concentration
c) Log of the hydrogen ion (H+) concentration
d) Negative log of the H+ concentration
e) Ratio of H+/OH concentration

28- This reaction is known as: NH4+ + OH

a) First order reaction
b) Ionization reaction
c) Neutralization reaction
d) Equilibrium reaction
e) Protonated reaction

H2O + NH3

29- Correct statements regarding bioisosters may include:

I- Molecules containing one different group or atom but electronically
equivalent
II- May act as antagonist to a normal metabolite
III- Molecules that differs only in the length of the side chain
a) I only
b) III only
c) I and II only
d) II and III only
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Dr.Fatima Arain

Medicinal Chemistry

e) All are correct

30-Which of the following is the molecular structure of isotretinoin, used in
oral treatment of acne?
a) 13-CIS Retinoic acid
b) 13-TRANS Retinoic acid
c) 13-CIS-TRANS Retinoic acid
d) Retinoic acid
e) None of the above

31- The analgesic activity of morphine is dependent of which molecular

structure?
a) Phenolic hydroxyl group
b) p-phenyl-N-alkylpiperidine
c) Methyl substitution
d) Piperidine
e) Phenolic amino group
32- Imidazoline is a molecular structure that contain a heterocyclic ring and
belongs the molecular structure of:
a) Prazosin
b) Nifedipine
c) Atropine
d) Clonidine
e) Allopurinol

CORRECT ANWERS
MEDICAL CHEMESTRY
1- A

Dr.Fatima Arain

Medicinal Chemistry

Comments: Glycine is a phase II metabolism reaction also known as amino

acids conjugation reaction that undergoes conjugation with carboxylic acid
2- E
Comments: Atropine is an antimuscarinic agent having pyrrolidine and
piperidine heterocyclic rings on its molecular structure.
3- A
Comments: Vinyl group is the univalent group CH2:CH.
4- E
Comments: Epimerization is the reaction responsible for the transfer of
tetracycline to epi-tetracycline
5- A
Comments: 5- Terminal alkyl group easily undergoes oxidation to an acid.
6- C
Comments: Acetylation is a phase II metabolism reaction characterized by
the gain of an acyl group, and the main reaction that undergoes primary
amines.
7- C
Comments: Isomers are compounds that have the same molecular formula
but different chemical structure, hexane and 1-methyl-pentane are examples
of isomerism.
8- D
Comments: Parasympathetic cholinergic drugs have their effect based on
nature of their structural molecule. To be effective, cholinergic drugs most
display a quasi-ring conformation. One methyl group of the
trimethylammonium group can be replaced by an ethyl group with only
slight loss of activity
9- C
Comments: Conjugations are phase II metabolism reactions characterized by
an incorporation of endogenous substrate on the molecular structure of drugs
normally coming from phase I metabolism reaction. Molecular structures
(drugs) having carboxylic acid, amide, alcohol and/or thio group are mainly
metabolized by a conjugation.

Dr.Fatima Arain

Medicinal Chemistry

10- C
Comments: In order for an antihistaminic drug be effective, they must have a
terminal tertiary nitrogen and more than one aryl or heretoaryl group on their
molecular structure.
11- A
Comments: Molecules may be classified as more or less reactive depending
in the presence of hydrogen and oxygen. Less hydrogen molecules and more
oxygen molecules increase the reactivity of the compound or substance.
12- C
Comments: Conformational isomerisms are stereoisomers produced by
rotation around single bond, typically rapidly interconverting at room
temperature. They are normally classified as enantiomers and diastereomers.
13- C
Comments: Geometric isomers may be classified as CIS and TRANS
depending the spatial position of the molecule around a bond with restricted
rotation. 2-Butene is an example of molecule having geometric isomerism.
14- A
Comments: Equatorial-equatorial is a structural formation of a molecule
occurring at the same distance from each extremity of an axis.
15- B
Comments: Choracetic acid is stronger than acetic acid due to higher
molecular weight
16- D
Comments: Nifedipine is calcium channel blocker that has 1,4dihydropyridine on its structure responsible for its mechanism of action.
17- A
Comments: Vitamin K has a quinolone on its molecular structure.
18- E
Comments: As much higher is the pKa of the drug stronger will be the acid.
19- D

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Dr.Fatima Arain

Medicinal Chemistry

Comments: Most of the steroid compounds have three cyclohexanes and

one cyclopentane ring on their molecular structure.
20- B
Comments: Glucuronidation is the main reaction of phase II metabolism
reactions, and are responsible mainly for the metabolism of drugs having
hydroxyl, carboxyl and amide group on their molecular structure.
21- C
Comments: Chloracetic acid is one of the strongest acids due to its molecular
structure.

22- A
Comments: Amides and esters are the only groups undergoing hydrolysis.
23- D
Comments: Phenol is a weak acid due to stable anion resonance
24- E
Comments: Molecules may be classified as more or less water-soluble
depending in the presence of hydrogen and oxygen. Less hydrogen
molecules and more oxygen molecules increase the water solubility of the
compound or substance.
25- B
Comments: Diastereomers must have more than one stereogenic center and
are not mirror image, they have superimposed image.
26- B
Comments: R-COOH is an acid while R-OH is not due to presence of stable
anionic resonance, an indication of the extent of activity of free radicals in
an organic reaction.
27- D
Comments: pH is the measure of the acidity or basicity of a solution that is
calculated mathematically as the negative log of the H+ concentration
28- C

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Dr.Fatima Arain

Medicinal Chemistry

Comments: NH4+ + OH H2O + NB3 is an example of

neutralization reaction.
29- C
Comments: Bioisosters are functional group or atoms that impact similar
physical and chemical properties on biological activity of molecule.
30- A
Comments: The molecular structure of isotretinoin, used in oral treatment of
acne is 13-CIS Retinoic acids. The TRANS molecular structure is only used
in topical preparations.
31- B
Comments: The analgesic activity of morphine is dependent of p-phenyl-Nalkylpiperidine
32- D
Comments: Clonidine is an antihypertensive drug that depends of its
imidazoline molecular structure to be effective.

BIBLIOGRAPHIC REFERENCE
1- COMPREHENSIVE PHARMACY REVIEW Lippincott William &
Wilkins Fourth edition
2- CPS-COMPENDIUM OF PHARMACEUTICALS AND SPECIALITIES
- Canadian Pharmacist Association 2001 edition.
3- MEDICAL DICTIONARY Dorlands illustrated 27th edition.
4- PHARMACY PREP Lectures series & study guide for Evaluating
Examination-TIPS - 2003/2004

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Dr.Fatima Arain

Medicinal Chemistry

5- THERAPUTIC CHOICES Canadian Pharmacist Association -Third

edition
6- USP DI Drug Information for the Health Care Professional15th edition
Volume I.

Prepared By?
Dr.Fatima Arain
Pharm-D
The University of Faisalabad;Madina
University Pakistan

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