Notesale: Turn your study into money

Document Preview

Extracts from the notes are below, to see the PDF you'll receive please use the links above

---

Pharmaceutical Organic Chemistry

1
...

b
...

d
...


As the bond polarity increase, the bond length decreases
A C-F bond has a longer bond length than C-C
As bond polarity increases the bond length also increases
A and B only
B and C only

2
...

b
...

d
...


As the s character increases, the bond length increases
As the s character increases, the bond length decreases
The bond length of acetylene is longer than the bond length of ethylene
The bond length of ethane is shorter than the bond length of ethylene
None of the choices

3
...
Which of the following
statements is/are true regarding its relationship with orbital hybridization, bond length and bond
poarity?
a
...

c
...

e
...

All of the choices
A and B only

4
...

b
...

d
...


4 methyl hexane
Isohexane
3-methyl hexane
2-ethyl pentane
2-propyl butane

5
...

b
...

d
...


2-methylpentene
4-methylpentene
2-methylpentane
4-methylpentene
2-methylpentyne

6
...
1- pentyne
b
...
4-pentyne
d
...
A and B
7
...
What is the name of the
following structure?

a
...

c
...

e
...
The structure of nucleic acid base cytosine, uracil and thymine is based on following N-ring
...

b
...

d
...


Pyridine
Piperidine
Pyrazine
Piperazine
Pyrimidine

9
...
The behaviour of these groups in an aqueous environment will influence the
activity of the drug and its absorption in the different compartments of the body
...

b
...

d
...
All of the above
10
...
Indomethacin (pKa=4
...
Ephedrine (pKa=9
...
Both indomethacin and ephedrine will be absorbed from the stomach rather than the
intestinal mucosa
d
...
A and B only
11
...
They commonly
undergo halogination and combustion reaction and, in vivo, terminal carbon or side chain
hydroxylation may occur
...

b
...

d
...


Alkanes
Alkenes
Aromatic hydrocarbon
Alkynes
Alkyl halides

12
...
Their
common reactions are the addition of hydrogen or halogenation, hydration (to form glycols), and
oxidation (to form peroxides)
...

b
...

d
...


Alkanes
Alkenes
Aromatic hydrocarbon
Alkynes
Alkyl halides

13
...
These molecules exhibit multicenter
bonding, which confers unique chemical properties
...

b
...

d
...


Alkanes
Alkenes
Aromatic hydrocarbon
Alkynes
Alkyl halides

14
...

b
...

d
...


Methanol
Ethanol
Propanol
Butanol
Phentanol

15
...

b
...

d
...


Primary alcohols are oxidized to ketones
Secondary alcohols are oxidized to aldehydes and then to acids
Tertiary alcohols ordinarily are not oxidized
A and B only
All of the statements are correct

16
...

b
...

d
...


Aldehydes
Ether
Phenols
Ketones
Esters

17
...
The
common reactions of these compounds are oxidation and hemiacetal and acetal formation
...
Aldehydes
b
...
Phenols
d
...
Esters
18
...

b
...

d
...


Branching decreases water solubility
Secondary amines are more water soluble than primary amines
Tertiary amines are the least water soluble compared to primary and secondary amines
A and B only
A and C only

19
...

a
...
Ether

c
...
Amides
e
...
These compounds have a general formula of RCOOH and commonly undergo salt formation
with bases, esterification and decaroxylation
...

b
...

d
...


Ketones
Ether
Esters
Amides
Carboxylic acid

21
...


b
...


d
...


22
...

b
...

d
...


Acetylation
Reductive cleavage
Oxidative deamination
Decarboxylation
N-dealkylation

23
...


A carboxylic acid group

II
...

a
...

c
...

e
...
For questions 24-26, refer to the drug molecule :

The drug molecule is soluble in
I
...

An aqueous acid
III
...

b
...

d
...


I only is correct
III only is correct
I, II, III are correct
II and III are correct
I and III are correct

25
...

b
...

d
...


Hydrolysis of the ester
Reduction of the carboxylic acid
Oxidation of the ester
A and B only
B and C only

26
...

II
...


Ring hydroxylation
Glucuronide formation
Enzymatic hydrolysis

a
...

c
...

e
...
Which of the following statements is/are true regarding drugs?
a
...
No drug is totally safe
c
...
Drugs used in high dosed can be considered as poisons
e
...
Most drugs bind to their targets by means of intermolecular bonds
...
An ionic or electrostatic bond is the strongest of the intermolecular bonds and takes
place between groups having opposite charges
b
...
Van der Waals forces of interaction are cost by transient dipole-dipole interaction
d
...
A and C only
29
...

b
...

d
...


IV, III, II, I
I, II, III, IV
II, III, I, IV
I, III, IV, II
III, II, I, IV

30
...

a
...

c
...

e
...
These type of inhibitor binds to the enzyme substrate complex in which its effect cannot be
overcome by increasing the substrate concentration
a
...
Irreversible inhibitor
c
...
Uncompetitive inhibitor
e
...
Which of the following drugs is incorrectly match with its target enzyme?
a
...

c
...

e
...
This type of inhibitor binds to a binding site different from the active site
...

a
...

c
...

e
...
Evaluate the following statements: Antagonists can mimic the natural messengers and activate
receptors
...

a
...

c
...


Both statements are correct
Both statements are incorrect
Only the first statement is correct
Only the second statement is correct
...
The following factors must be considered in designing an agonist:
a
...

c
...

e
...

Specific functional groups must be correctly positioned
...

A and B only
All of the above

36
...

II
...


IV
...

Examples of structurally non specific drugs are 6-mercaptopurine, phenothiazines,
pyrimethamine, and primaquine
...
Chemical
reactivity of the drug plays an important role as reflected in bonding propensities and
exactness of fit on the receptors
...


a
...

c
...

e
...
Which of the following drug-enzyme pairs is/are correctly matched?
I
...
Cephalosphorins – transpeptidase
III
...
Epinephrine – Adenylyl cyclise
a
...

c
...

e
...
It is generally conceived that an exact fit of the drug molecule and receptor is necessary to evoke
maximal biologic response that is imperative to consider the stereochemical makeup of drugs
...
Only the (-) isomer of ascorbic acid has antiscorbutic activity\
II
...

III
...
Only the D(threo) isomer has high anti-bacterial activity
a
...

c
...

e
...
What is the rate-limiting step in drug absorption of orally administered solid dosage forms?
a
...

c
...

e
...
Which of the following factors can influence the dissolution rate of drugs from solid dosage forms
and hence, the therapeutic activity?
I
...

III
...


Solubility, particle size, crystalline form and salt form of the drug
Rate of disintegration in the gastrointestinal lumen
Gastric pH, motility and presence of food at the absorption site
I only is correct

b
...

d
...


III only is correct
I, II, and III are correct
II and III are correct
I and III are correct

41
...

II
...


IV
...

b
...

d
...


Renal excretion involves three processes: glomerular filtration, secretion and tubular
reabsorption
...

Drugs with high lipid/water partition coefficients are reabsorbed readily while those with
low lipid/water partition coefficients are unable to diffuse back across the tubular membrane
and are excreted in the urine unless reabsorbed by an active carrier system
...

I only is correct
III only is correct
I, III, and IV are correct
I, II, and IV are correct
I, II, III, and IV are correct

42
...


II
...

IV
...

b
...

d
...


Phase I reactions include oxidation, hydroxylation, reduction and hydrolysis-enzymatic
reactions in which a new functional group in introduced into the drug molecule or an existing
functional group is modified making the drug more polar and more readily excreted
...

Most drugs undergo phase I reactions only
...

I only is correct
III only is correct
I, III, and IV are correct
I, II, and IV are correct
I, II, III, and IV are correct

43
...

II
...

IV
...

b
...

d
...

Imipramine is converted to Despiramine by O-dealkylation
Amphetamine is converted to Phenylacetone by deamination
II only is correct
III only is correct
I and IV are correct
II and III are correct

e
...
Phase I metabolic transformation introduce new and polar functional groups into the molecule,
which may produce one or more of the following changes, except:
a
...

c
...

e
...
Which of the following Phase II pathway is correctly paired with their activated conjugating
immediate?
I
...

III
...

a
...

c
...

e
...

Sulfonamides can undergo which metabolic pathway?
I
...

III
...


a
...

c
...

e
...
The first purely synthetic antimicrobial drug which was developed by Paul Erlich
...

a
...

c
...

e
...
Which of the following antibacterial agents acts by inhibiting the metabolism of microbial
organism but not of the host?
a
...

c
...

e
...
Which of the following antibacterial agents inhibit s bacterial cell wall synthesis?
a
...

c
...

e
...
Which of the following antibacterial agent can interact with the plasma membrane of bacterial
cells to affect membrane permeability?
a
...

c
...

e
...
Which of the following antibacterial agents can disrupt the synthesis of essential proteins and
enzyme required for the cell’s survival?
a
...

c
...

e
...
This antibacterial agent can inhibit the nucleic acid transcription and replication which prevents
cell division and
...

a
...

c
...

e
...
For questions 53-55, refer to the general structure of sulphonamides below:

Which part of the drug’s structure is essential for drug activity?
a
...

c
...

e
...
Which of the following statements is/are correct regarding the structure-activity relationship of
sulphonamides?
I
...

III
...

b
...

d
...


The p-amino group must be unsubstituted unless it is a prodrug or when the body can further
metabolize it to generate the active compound
...

The sulphonamide nitrogen must be primary or secondary
...
Which part of the drug molecule can only be varied to retain the antibacterial activity?
a
...

c
...

e
...
A sulphonamide used in combination with pyrimethamine in the treatment of Malaria
...

b
...

d
...


Sulfadiazine
Sulfathiazole
Sulfadoxine
Sulfamethoxazole
Sulfones

57
...
It inhibits the
enzyme dihydrofolate reductase leading to the inhibition of DNA synthesis and cell growth
...

b
...


Pyrimethamine
Trimethoprim
Pralidoxime

d
...


Cotrimoxazole
Fansidar

58
...

a
...

c
...

e
...
Below is the general structure of penicillins
...

b
...

d
...


The free carboxylic acid
The strained B-lactam ring
The acyl amino side chain
The bicyclic system
The sulphur atom

60
...

b
...

d
...


resistant to acid hydrolysis
Protected from B-lactamase enzymes
Broaden the spectrum of activity
A and B only
All of the above

61
...

b
...

d
...


It will make the drug stable in acidic conditions
...
This drug is a penicillin analogue with isoxazolyl incorporated in the acyl side chain making it
useful against Staphylococcus aureus infections and acid resistant
...

b
...


Flucloxacillin
Ampicillin
Carbenicillin

d
...


Piperacillin
Tazobactam

63
...

b
...

d
...


Azlocillin
Mezlocillin
Ticarcillin
Piperacillin
None of the choices

64
...

b
...

d
...


Azlocillin
Mezlocillin
Ticarcillin
Piperacillin
None of the choices

65
...

b
...

d
...


Alanine
Cysteine
Valine
A and B only
B and C only

66
...

b
...

d
...


Cephalosporins contain a bicyclic system containing a 4-membered B-lactam ring
...

Biosynthetic precursors of its skeleton is the same as that of penicillins
...
Which of the following statements correctly describe/s the structure of carbapenems such as
imipenem and meropenem?
a
...

c
...

e
...
Clavulanic acid is a beta-lactamase inhibitor used in combination with amoxicillin and other Blactamase antibiotics
...

b
...

d
...


Clavulanic acid has a strained lactam ring in its structure
...
Clavulanic acid, Sulbactam and tazobactam are B-lactamase inhibitors that act as suicide
substrates are administered with B-lactam antibiotics to prevent their degradation
...

b
...

d
...


Sulbactam + Piperacillin = Zosyn
Tazobactam + Ticarcillin = Timentin
Clavulanic acid + amoxicillin = Augmentin
A and B only
A and C only

70
...

a
...

c
...

e
...
A polypeptide complex produced from Bacillus subtilis that binds and inhibits the carrier lipid
responsible for carrying the cell wall components across the cell membrane
...

b
...

d
...


Bacitracin
Vancomycin
D-cycloserine
Aztreonam
Teicoplanin

72
...

a
...

c
...

e
...
A glycopeptide antibiotic isolated from Actinomyces teichomyceticus
a
...

c
...


Bacitracin
Vancomycin
D-cycloserine
Aztreonam

e
...
An antibiotic composed of 16 amino acids that is described as a ‘tunnelling’ molecule that act on
the plasma membrane and result in the uncontrolled movement of ions across cell membrane
leading to cell death
...

b
...

d
...


Daptomycin
Gramicidin A
Valinomycin
Polymyxin B
All of the above

75
...
This ionophore is specific for potassium ions over sodium ions
...

b
...

d
...


Daptomycin
Gramicidin A
Valinomycin
Polymyxin B
All of the above

76
...

a
...

c
...

e
...
A cyclic lipopeptide derived from a bacterial strain of Streptomyces roseosporus and works by
disrupting multiple functions of bacterial cell membrane
...

b
...

d
...


Daptomycin
Gramicidin A
Valinomycin
Polymyxin B
All of the above

78
...
This
antibiotic contains a carbohydrate and basic amine groups in its structure
...

b
...

d
...


Chlortetracycline
Streptomycin
Chloramphenicol
Lincomycin
Erythromycin

79
...
This drug was isolated from Streptomyces
aureofasciens
...

b
...

d
...


Chlortetracycline
Streptomycin
Chloramphenicol
Lincomycin
Erythromycin

80
...

b
...

d
...


Chlortetracycline
Streptomycin
Chloramphenicol
Lincomycin
Erythromycin

81
...

b
...

d
...


Chlortetracycline
Chloramphenicol
Erythromycin
A and B only
B and C only

82
...

b
...

d
...


Streptomyces griseus
Streptomyces pristinaespiralis
Acremonium chrysogenu
Streptomyces nodosus
Streptomyces erythreus

83
...

b
...

d
...


Quinupristin
Linezolid
Ofloxacin
Metronidazole
Proflavine

84
...
Which of the following
is related to nalidixic acid?

a
...

c
...

e
...
An aminoacridine agent used topically to treat deep surface wounds
...

a
...

c
...

e
...
The antibiotic isolated from Streptomyces mediterranei which inhibits Gram positive bacteria and
works by binding noncovalently to DNA-dependent RNA polymerase and inhibiting the start of RNA
synthesis
...

a
...

c
...

e
...
A nitroimidazole structure introduced as an anti-protozoal agent and later became anti bacterial
agent
...

a
...

c
...

e
...
A drug used to treat urinary tract infections where it degrades in acid conditions to give
formaldehyde as the active agent
...

b
...

d
...


Rifamycin B
Methenamine
Metronidazole
Isoniazid
Nitrofurantoin

89
...
It specifically inhibits viral DNA polymerase and
used in the treatment of infections due to herpes simplex 1 and 2 as well as varicella-zoster viruses
...

b
...

d
...


Acyclovir
Idoxuridine
Podophyllotoxin
Fomivirsen
Imiquimod

90
...

b
...

d
...


Cidofovir
Penciclovir
Valaciclovir
Famciclovir
Ganciclovir

91
...

a
...

c
...

e
...
A plant product used in the treatment of genital warts caused by DNA virus papilloma virus
...

b
...

d
...


Acyclovir
Idoxuridine
Podophyllotoxin
Fomivirsen
Imiquimod

93
...
It is a DNA antisense
molecule that blocks the translation of viral RNA and is used against retinal inflammation caused by
CMV in AIDS patients
...

b
...

d
...


Acyclovir
Idoxuridine
Podophyllotoxin
Fomivirsen
Imiquimod

94
...

a
...

c
...

e
...
The anti-HIV drug contains inosine as the nucleic acid base and is converted through a series of
enzyme reaction to 2’,3’-dideoxyadenosine triphosphate which is the active drug
...

b
...

d
...


Zidovudine
Didanosine
Lamivudine
Abacavir
Efavirenz

96
...

b
...

d
...


Zidovudine
Didanosine
Lamivudine
Abacavir
Efavirenz

97
...

a
...

c
...

e
...
A second generation non-nucleoside reverse transcriptase inhibitor that has a benzoxaxinone
structure
...

b
...

d
...


Zidovudine
Didanosine
Lamivudine
Abacavir
Efavirenz

99
...

b
...

d
...


NRTIs are prodrugs that are converted by cellular enzymes to active triphosphates which
act as enzyme inhibitors and chain terminators
...

PIs are designed to act as transition state inhibitors
A and B only
All of the above

100
...
Which part of its structure is essential for drug activity?

a
...

c
...

e
...
Which substituent of chloramphenicol is responsibe for its toxic effect?
a
...

c
...

e
...
Which of the following statements is correct regarding Erythromycin?
I
...

III
...


a
...

c
...

e
...


Erythromycin binds to the 50s subunit of bacterial ribosomes
When administered together with chloramphenicol, their bacteriostatic effect will increase
...

Increasing the size of the macrocycle to a 16-membered ring can increase the acid stability
of the molecule
...
Which of
the following statements is correct regarding amantadine?
I
...

II
...

III
...
At high concentrations, it can alter pH of endosomes and prevent the acidic
environment required by the hemagglutinins to fuse the viral membrane with
that of the endosome
...

b
...

d
...


I, II, III, IV
I, III, IV
I, II, IV
II, III
III, IV

For nos
...
Which among the given structures can be intercalating agent which can slide between the base
pairs of the DNA double helix and thereby can inhibit the enzymes involved in the replication and
transcription processes?
a
...

c
...

e
...
Which among the given structures is an antimetabolite that can inhibit the enzymes involved in
the synthesis of DNA or its nucleotide building blocks?
a
...

c
...

e
...
Which of the given structures can form strong covalent bonds with the nucleophilic groups on
DNA which can eventually result to cross-linking of strands?
a
...

c
...

e
...
Which of the given structures can be classified as an alkylating agent?
a
...

c
...

e
...
A semi-synthetic analogue of camptothecin given intravenously and is a prodrug used in
combination with fluorouracil and folinic acid for the treatment of advanced colorectal cancer
...

b
...

d
...


Oblimersen
Calicheamicin
Carboplatin
Irinotecan
Cyclophosphamide

109
...

a
...

c
...

e
...
A natural product that reacts with nucleophiles to produce diradical species
...

a
...

c
...

e
...
It is the most commonly used alkylating agent in cancer chemotherapy, the metabolism of
which produces arcolein which is toxic to the bladder and kidneys
...

b
...

d
...


Oblimersen
Calicheamicin
Carboplatin
Irinotecan
Cyclophosphamide

112
...

a
...


Oblimersen
Calicheamicin

c
...

e
...
Which of the following drugs is not an alkylating agent used in cancer chemotherapy?
a
...

c
...

e
...
A thiopurine prodrug which is converted to its corresponding monophosphate that inhibits
purine synthesis
...

b
...

d
...


Methotrexate
5-fluorouracil
6-mercaptopurine
Pentostatin
Cytarabine

115
...
It inhibits the enzyme dihydrofolate reductase which is responsible in
maintaining levels of the enzyme cofactor tetrahydrofolate
...

b
...

d
...


Methotrexate
5-fluorouracil
6-mercaptopurine
Pentostatin
Cytarabine

116
...
It is converted in the body to the fluorinated
analogue of 2’deoxyuridylic acid monophosphate which then combines with the enzyme thymidylate
synthase and the cofactor
...

b
...

d
...


Methotrexate
5-fluorouracil
6-mercaptopurine
Pentostatin
Cytarabine

117
...

a
...

c
...

e
...
A prodrug analogue of 2’deoxycytidine which inhibits DNA polymerases
...

b
...

d
...


Methotrexate
5-fluorouracil
6-mercaptopurine
Pentostatin
Cytarabine

119
...

II
...

IV
...

b
...

d
...


Glucocorticoids: Megestrol acetate
Progestins: prednisone
Estrogens: Diethylstilbestrol
Androgens: Fluoxymesterone
I, II, III, IV
I, II
III, IV
I, III
II, IV

120
...

a
...

c
...

e
...
A reversible competitive inhibitor of the enzyme aromatase , the design of which is based on
structure of amino gluthetimide
...

b
...

d
...


Goserelin
Raloxifene
Cyproterone acetate
Anastrazole
4-hydroxyandrostenedione

122
...

a
...

c
...

e
...
This mode of therapy involves the delivery of a gene that codes for an enzyme capable of
activating an anticancer prodrug into a cancer cell
...

b
...

d
...


Antibody-directed enzyme prodrug therapy (ADEPT)
Antibody-directed abzyme prodrug therapy (ADAPT)
Gene -directed enzyme prodrug therapy (GDEPT)
Photodynamic therapy
All of the above

124
...

a
...

c
...

e
...
This therapy involves an antibody-enzyme conjugate that is targeted to specific cancer cells
...

a
...

c
...

e
...
Which of the following statements is true regarding acetylcholine?
I
...

III
...

a
...

c
...

e
...

It is easily hydrolyzed in the stomach by acid catalysis and cannot be given orally
...

There is no selectivity of action upon administration of acetylcholine
...
127-129, refer to the structure of acetylcholine below;

127
...

b
...

d
...


The quaternary nitrogen
The ester functional group
The ethylene bridge between the ester and nitrogen
All of the above
None of the choices

128
...

b
...

d
...


The quaternary nitrogen
The ester functional group
The ethylene bridge between the ester and nitrogen
All of the above
None of the choices

129
...

b
...

d
...


Replacing the nitrogen atom with a neutral carbon atom increases the activity
The overall size of the molecule cannot be altered greatly
...

A and B
B and C

130
...

b
...

d
...


Addition of steric shield in the ethylene bridge renders resistance to chemical and enzymatic
hydrolysis
Changing the ester to a carbamate increases resistance to hydrolysis
Changing the ester to a carbamate makes it selective to muscarinic receptor
A and B
B and C

For nos
...
Which of the given structures is more stable to acid hydrolysis than acetylcholine?
a
...

c
...

e
...
Which of the given structures is more selective to muscarinic receptor than nicotinic receptor?
a
...

c
...

e
...
Given below is the general structure of muscarinic antagonists which was mostly based on the
structure of atropine
...

b
...

d
...


The alkyl group on nitrogen can be larger than methyl
The nitrogen can be tertiary or quaternary
Very large acyl groups (R1 and R2) are allowed
A and B only
All of the above

134
...
Which of its functional group/s
is/are essential for its activity?

a
...

c
...


Carbamate group
Benzene ring
Pyrrolidine ring
A and C only

e
...
135-141, refer to the general structure below:

135
...

b
...

d
...


The 2 phenolic groups
Secondary alcohol
Ionized amine
The aromatic ring
A and B only

136
...

b
...

d
...


The 2 phenolic groups
Secondary alcohol
Ionized amine
The aromatic ring
A and B only

137
...

b
...

d
...


The 2 phenolic groups
Secondary alcohol
Ionized amine
The aromatic ring
A and B only

138
...

b
...

d
...


The 2 phenolic groups
Secondary alcohol
Ionized amine
The aromatic ring
A and B only

139
...

b
...

d
...


Removal of the phenolic groups
A and B only
B and C only

140

---