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Title: Pharmaceutical Organic Chemistry
Description: Pharmaceutical Organic Chemistry Questions and answers helpful for reviews and board exams.
Description: Pharmaceutical Organic Chemistry Questions and answers helpful for reviews and board exams.
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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
...
b
...
d
...
Increasing the size of N-alkyl substituent
Addition of an alpha methyl group
Removal of the phenolic groups
A and B only
B and C only
141
...
b
...
d
...
Increasing the size of N-alkyl substituent
Addition of an alpha methyl group
Removal of the phenolic groups
A and B only
B and C only
For nos
...
Which of the following statements is true about the SAR of aryloxypropranolamines?
a
...
c
...
e
...
The alcohol group on the side chain is essential for activity
...
A and B only
B and C only
143
...
b
...
d
...
Heteroaromatic rings can be introduced to the system
...
Adding an N-arylethyl group is detrimental
...
A, B, and C only
144
...
b
...
d
...
145
...
II
...
IV
...
b
...
d
...
Replacement of sulphur for the carbonyl oxygen at carbon 2
results in quick onset and short duration of action
...
The
greater the branching, the more potent the drug
...
Methylation of one of the imide hydrogens (the transition from
5,5-disubstituted barbituric acid to 1,5,5-trisubstituted barbituric acid)
increases onset and decreases duration of action
...
Which of the following statements describe the ideal antiepileptic drug?
I
...
III
...
a
...
c
...
It should completely suppress seizures in doses that also cause sedation
...
It should have a long duration of effect after oral administration for prevention of recurrent
seizures
...
I, II, III, and IV are correct
147
...
b
...
d
...
It is also known as Phenobarbital
The sedative-hypnotic effect of this drug limits its use in older children and adults
It exhibits anticonvulsant effects in doses that do not cause sedation
...
Which of the following statements correctly describe 2-ethyl-2-methylsuccinide?
a
...
c
...
e
...
It can cause ataxia and gingival hyperplasia
...
A and B only
B and C only
149
...
b
...
d
...
It is widely accepted treatment of petit mal condition
...
It is also known as Dilantin
...
Which of the following statements correctly describe the structure-activity relationship of tricyclic
psychotropic drugs?
I
...
III
...
a
...
c
...
e
...
Dihenylalamine and Diphenylmethane derivatives that lack a central ring are devoid of
psychotropic activity
...
Rigidly planar tricyclic diphenylmethane derivatives such as anthracene are inactive
...
151
...
Antipsychotic effect
II
...
Anti-adrenergic, anticholinergic, antihistaminic and antiserotonin effects
IV
...
I only is correct
D
...
III only is correct
E
...
II, III,IV are correct
152
...
thioridazine
II
...
Droperidol
IV
...
I only is correct
D
...
IV only is correct
E
...
I and II are correct
For numbers
...
Which of the following statement is/are true regarding modifications at the phenolic function at
position 3?
A
...
B
...
C
...
D
...
B and C only
154
...
Masking the hydroxyl group at position 6 increases all morphine type effects
...
6-ethylmorphine and 3,6-diacetylmorphine are more potent than morphine itself
...
The oxygen function at position 6 is essential for analgesic activity
D
...
B and C only
155
...
Reduction of the 7-8 double bonds in morphine results in a decrease in activity
...
Dihydromorphine and dihydrocodeine is more potent than the parent compound morphine
...
Unsaturation is essential for activity
D
...
B and C only
156
...
Conversion of the tertiary nitrogen to a quaternary nitrogen results in a decrease of analgesic
activity
B
...
C
...
D
...
B and C
157
...
Digoxin is more toxic than digitoxin because of its additional hydroxyl group that makes it
more lipophilic
...
Digoxin is less toxic than digitoxin because of its additional hydroxyl grouo that makes it
more hydrophilic
...
Digoxin has longer duration of action than digitoxin
...
A and B
E
...
What is the probable mechanism of action of cardiac agent with the following structure?
O₂NO
CH ₂
CH ONO ₂
O ₂ NO
CH ₂
A
...
It relaxes the vascular smooth muscle (vasodilation)
C
...
It blocks the beta adrenergic receptor
E
...
A drug used in the treatment in myocardial insufficiency that is structurally similar to adenosine,
a natural vasodilatory substance released by the myocardium during hypoxic episodes
...
Cyclandelate
D
...
Dypirydamole
E
...
Papaverine
160
...
A
...
Flecainide
D
...
Procainamide
C
...
An antiarrythmic drug that is an ᾳ-methyl analog structurally related to monoethylglycinexylide,
the active metabolite of xylocaine
...
Disopyramide
B
...
Tocainide
E
...
quinidine
162
...
It blocks the platelet phosphodiesterase enzyme, therefore leading to higher cyclic
adenosine monophosphate levels
...
It reversibly inhibits the cyclooxygenase enzyme
C
...
A and C only
E
...
Which of the following statement is true regarding agonist at the H1 and H2 receptor antagonist
of histamine?
A
...
H2 antagonist are hydrophobic molecules thus they are less likely to produce cns side
effects
C
...
A and B only
E
...
Which of the following statements correctly describes the ideal anesthetic agent?
I
...
It should produce rapid and uncomplicated induction and emergence
III
...
IV
...
I, II, III, IV
D
...
II,III,IV only
E
...
II & III only
165
...
Along with toxicity, increasing the chain length of ethers increases the anesthetic activity
...
Along with toxicity, increasing the chain length of ethers decreases the anesthetic activity
...
Introduction of unsaturation into an aliphatic ether increases potency and shortens
induction and emergence
IV
...
I,IV only
D
...
I,III only
E
...
II,III only
166
...
Addition of halogen atoms to ethers or hydrocarbons decreases flamability
II
...
III
...
Addition of halogen atoms to ethers or hydrocarbons often decreases anesthetic potency
...
I & II only
D
...
I & IV only
C
...
Which of the following metabolic transformation of barbiturates can lead to loss of depressant
activity?
A
...
Desulfuration of 2-thiobarbiturates
C
...
All of the above
E
...
Which of the following acids has mycobacteriostatic activity?
A
...
Chaulmoogric acid
C
...
Salicylic acid
E
...
Which of the following alcohols has a local anesthetic property?
A
...
2-propanol
C
...
2-pyridinemethanol
E
...
Which of the following amino ethers has antihistamine property?
A
...
Benzidioxanes
C
...
Phenoxybenzamine
E
...
Which of the following halogenated compounds has hypnotic properties?
A
...
Carbon tetrachloride
C
...
Hexachlorophene
E
...
Which of the following statements is correct regarding the structural features of cetirizine and
clemastine?
A
...
Cetirizine will more likely cause drowsiness than clemastine
C
...
A and B only
E
...
Which of the following functional groups can decrease the absorption of cetirizine and
clemastine through the blood brain barrier?
A
...
Tertiary amines
C
...
A and B
E
...
Which of the following functional groups can increase the absorption of cetirizine and
clemastine through the blood brain barrier?
A
...
Tertiary amines
C
...
A and B
E
...
If a truck driver asks you to recommend an antihistamine drug for his seasonal allergies, which
of the two drugs will you recommend?
A
...
Cetirizine
C
...
None of the choices
176
...
You recommended terbinafine, an effective topical antifungal agent
that is sold over the counter
...
Aromatic hydrocarbon
B
...
AlkyneAll
D
...
All of the above
177
...
Valine
B
...
Alanine
D
...
Serine
178
...
Phenylalanine
B
...
Threonine
D
...
Arginine
179
...
Tripelennamine
B
...
Promethazine
D
...
All of the above
180
...
Tripelennamine
B
...
Promethazine
D
...
All of the above
181
...
Tripelennamine
B
...
Promethazine
D
...
All of the above
182
...
Tripelennamine
B
...
Promethazine
D
...
All of the above
183
...
Rate theory
B
...
Activation aggregation theory
D
...
Molecular pertubation theory
184
...
A
...
Occupational theory
C
...
Induced fit theory
E
...
This drug receptor theory suggest that the drug approaches the receptor, a conformational
change occurs in the receptor to allow effective binding
...
Rate theory
B
...
Activation aggregation theory
D
...
Molecular pertubation theory
186
...
Agonist function by shifting the equilibrium toward the activated state, whereas
antagonist prevent the activated state
...
Rate theory
B
...
Activation aggregation theory
D
...
Molecular pertubation theory
187
...
A
...
Occupational theory
C
...
Induced fit theory
E
...
Which of the following statements correctly describes an agonist?
A
...
They may have similar structure to the ligand
C
...
A and B
E
...
Which of the following statements correctly describes an antagonist?
A
...
They may have similar structure to the ligand
C
...
A and B
E
...
These are exogenous chemical messengers that act as antagonist, but also eliminate any
resting acivity associated with a receptor
...
Partial agonist
B
...
Hormones
D
...
None of the choices
191
...
A
...
Desensitization
C
...
Dependence
E
...
This condition may occur when an antagonist is bound to a receptor for a long period of time
...
A
...
Desensitization
C
...
Dependence
E
...
This is a situation where increases doses of a drug over time to achieve same effect
...
Sensitization
B
...
Tolerance
D
...
None of the above
194
...
On stopping the drug,
withdrawal symptoms occur as a result of abnormal levels of target receptor
...
Sensitization
B
...
Tolerance
D
...
None of the above
195
...
A
...
Affinity
C
...
All of the above
E
...
This is determined by measuring the maximum possible effects resulting from receptor-ligand
binding
A
...
Affinity
C
...
All of the above
E
...
This relates how effective a drug is in producing a cellular effect
...
A
...
Affinity
C
...
All of the above
E
...
These are molecules that act as substrates for a target enzyme, but which are converted into a
highly reactive species as a result of the enzyme catalyzed reaction mechanism
...
A
...
Suicide substrates
C
...
Competitive inhibitor
E
...
This type of inhibition binds to a different site other than the active site and can alter the shape
of the enzyme such that the active site is no longer recognizable
...
Transition state analogue
B
...
Allosteric inhibitors
D
...
All of the above
200
...
They bind more strongly than either the substrate or product
...
Transition state analogue
B
...
Allosteric inhibitors
D
...
All of the above
201
...
A
...
Suicide substrates
C
...
Competitive inhibitor
E
...
Physostigmine inhibit which of the following enzyme?
A
...
Arabinosyl transferase
C
...
3’,5’-cyclic GMP phosphodiesterase
E
...
sildenafil, a drug for erectile dysfunction, inhibit which of the following enzyme?
A
...
Arabinosyl transferase
C
...
3’,5’-cyclic GMP phosphodiesterase
E
...
ethambutol, a drug for tuberculosis, inhibit which of the following enzyme?
A
...
Arabinosyl transferase
C
...
3’,5’-cyclic GMP phosphodiesterase
E
...
Which of the following drugs for diabetes inhibits the enzyme a-glucosidase?
A
...
Miglitol
C
...
Metformin
E
...
Which of the following drugs for diabetes inhibits the enzyme a-amylase?
A
...
Miglitol
C
...
Metformin
E
...
Which of the following drug (inhibitor)-enzyme inhibited pairs is incorrectly matched?
A
...
Itraconazole: sterol14a –methylase
C
...
All of the above
E
...
Which of the following drug (inhibitor)-enzyme inhibited pairs is incorrectly matched?
A
...
Mycophenolate: IMP dehydrogenase
C
...
All of the above
E
...
Which of the following drug (inhibitor)-enzyme inhibited pairs is correctly matched?
A
...
Etodolac: prostaglandin endoperoxide synthase
C
...
All of the above
E
...
Which of the following drugs (inhibitor) enzyme inhibited pairs is correctly matched?
A
...
Oseltamivir: viral neuraminidase
C
...
All of the above
E
...
Which of the following phenolic drugs has an expectorant activity?
A
...
Guaiacol
C
...
Diethylstilbestrol
E
...
Which of the following dyes is available as vaginal suppository for the treatment of yeast
infection and has also been used orally as a anthelmintic for strongyloidiasis and oxyurias?
A
...
Phenolpthalein
C
...
Methylrosaniline chloride
E
...
Which of the following dyes is a mixture of the chlorides of rosaniline and p-rosaniline? It is an
ingredient of castellanis paint which is used topically in the treatment of fungal infection, such as
ringworm and athletes foot?
A
...
Methylrosaniline chloride
B
...
None of the choices
C
...
It is a non classical folate antagonist that is structurally similar to methotrexate
...
A
...
Metronidazole
C
...
Suramin
D
...
Which of the following anti-inflammatory analgesic is an arylacetic derivative that is comparable
to aspirin in the treatment of rheumatoid arthritis, with a lower incidence of side effects? It has also
been approved for used in primary dysmenorrhea
...
Sodium salicylate
D
...
Mefenamic acid
E
...
Ibuprofen
216
...
Sodium salicylate
D
...
Mefenamic acid
E
...
Ibuprofen
217
...
A
...
Acetaminophen
B
...
antipyrine
C
...
The following are synthetic estrogens except:
A
...
B and C only
B
...
None of the choices
C
...
Which of the following estrogens is an estradiol metabolite originally obtained from the urine of
horses especially pregnant mares?
A
...
Diethylstilbestrol
B
...
Dienestrol
C
...
Which of the following progestins is classified as a derivative of testosterone?
A
...
Norethindrone
B
...
Ethinodiol acetate
E
...
Which of the following progestins are classified as derivative of testosterone?
A
...
A and B only
B
...
B and C only
C
...
Which of the following prodrugs was designed to improve the membrane permeability of its
active metabolite?
A
...
A and C only
B
...
All of the above
C
...
Which of the following prodrugs was designed to prolong the drug activity of its active
metabolite?
A
...
Chloramphenicol succinate
B
...
Hetacillin
C
...
Which of the following prodrugs was designed to lower water solubility of the active metabolite?
A
...
Chloramphenicol succinate
B
...
Hetacillin
C
...
Which of the following prodrugs was designed to mask the toxic side effects of its active
metabolite?
A
...
Chloramphenicol succinate
B
...
Hetacillin
C
...
Which of the following prodrugs was designed to increase the water solubility of the active
metabolite?
A
...
Chloramphenicol succinate
B
...
Hetacillin
C
...
Which of the following prodrug was designed to increase the chemical stability of the active
metabolite?
A
...
Azathioprine
C
...
Hetacillin
D
...
These are isomer that contain at least one assymetric, or chiral, carbon atom
...
A
...
All of the above
B
...
None of the choices
C
...
This type of isomer occurs as a result of restricted rotation about a chemical bond, owing to
double bond or rigid ring system in the molecule
...
Optical isomer
D
...
Geometric isomer
E
...
Conformational isomer
230
...
A
...
All of the above
B
...
None of the choices
C
...
Which of the following statements is true regarding ester-type local anesthetics?
A
...
They are generally short acting due to rapid hydrolysis in the plasma
C
...
A and B only
E
...
Which of the following statements is true regarding amide-type local anesthetics?
A
...
They are generally short acting due to rapid hydrolysis in the plasma
C
...
A and B only
E
...
Which of the following statements is true regarding the antipsychotic agents in the
phenothiazine class?
A
...
B
...
C
...
D
...
B and C only
234
...
butyrophenone, haloperidol
B
...
Thioxanthenes, thioridazine
D
...
All of the above
235
...
dihydroinolones, molindone
B
...
Dibenzodiazepines, clozapine
D
...
All of the above
236
...
Imipramine and clompramine are derivatives of dibenzazepine
B
...
TCA appear to produce their antidepressant effects by blocking the intraneuronal oxidative
deamination of brain biogenic amines
...
A and B only
E
...
Which of the following statements correctly describe the structure and mechanism of action of
mao inhibitors?
A
...
Phenelzine isocarboxacid are weakly potent hydralazine derivative
C
...
A and B only
E
...
238-240, select the most appropriate pharmacologic category for the following structures:
238
...
Opioid antagonist
D
...
Anxiolytic
E
...
Antidepressant
239
...
Opioid antagonist
D
...
Anxiolytic
E
...
Antidepressant
240
...
Opioid antagonist
D
...
Anxiolytic
E
...
Antidepressant
241
...
Opioid antagonist
D
...
Anxiolytic
E
...
Antidepressant
242
...
A
...
Histidine
B
...
Serine
C
...
Give the amino acid of the autacoids with the following structure
...
tyrosine
D
...
Phenylalanine
E
...
Tryptophan
244
...
Which of the following drugs produce such metabolites?
I
...
Demethylation of morphine
III
...
Isomerization of retinoic acid
A
...
II only
B
...
I only
C
...
Which of the following biotransformation produces a metabolite with an activity different from
that of their parent compound?
I
...
Demethylation of morphine
III
...
Isomerization of retinoic acid
A
...
II only
B
...
I only
C
...
Which of the following biotransformation produces a inactive metabolite
I
...
Demethylation of morphine
III
...
Isomerization of retinoic acid
A
...
II only
B
...
I only
C
...
Which of the following statements is true regarding oxidation reaction?
I
...
Oxidation reactions can occur in the liver
III
...
IV
...
I,II,III,IV
B
...
I and III Only
E
...
III, IV only
248
...
It has same goal as oxidation reaction to create polar functional groups that can be easily
excreted
...
Bacteria resident in the GI tract are also responsible for reductions of azo and nitro
groups
III
...
Cytochrome P450 enzymes is not involved in the reduction reaction
A
...
II and III only
B
...
IV only
C
...
Which of the following drugs is metabolized by CYP1A?
A
...
Theophyliine
B
...
All of the above
C
...
Which of the following drugs is metabolized by CYP4B?
A
...
Carbamazepine
C
...
Hydrocortisone
E
...
Which of the following statements is correct regarding Phase ll reactions?
l
...
These reactions require both a high-energy molecules and an enzyme
lll
...
drug,or the
lV
...
almost always
A)l,ll,lll,lV
C)land ll only
B) l,ll,lll only
E)lV only
D)ll and lll only
252
...
It is the most common conjugation pathway because of readiy available supply of
glucuronic acid as well
as a large variety of functional groups,which can enzymatically
react with this sugar derivative
...
The high energy form of glucuronic acid is Uridine monophosphate glucuronic acid and
involve in these reaction is glucuronyl transferase
...
Druds that posses hydroxyl or carboxyl functional groups readily undergo
and ethers,respectively
...
The addition of the glucuronide moiety greatly increases the hydrophilicity of the
it highly reabsorbed by the renal tubes
...
Which of the following conjugation reactions requires 2’-phosphoadenosine-5’- phosphosulfate molecule?
A) Glutathione conjugation
D) Sulfate conjugation
B) Acetylation
E) Amino acid conjugation
C) Methylation
254
...
Which of the following conditions can greatly affect the metabolism of a certain drug?
A) Congestive heart failure
B) Deficiency of certain dietary minerals
D) Increase drug dosage
E) All of the above
C) Deficiency of vitamins
256
...
Which of the following metabolites would be the least likely urinary excretion product of acetaminophen?
A) Ether glucuronide
B) Sulfate conjugate
C) N-acetyl-p-benziminoqiunoneimine
D) Unchange drug
E) N-acetyl-p-benziminoquinoneimine with glutathione
258
...
First and second generation Sulfonylureas have a bulk
aliphatic substituent on the nonsufonyl have relatively simple aromatic
ll
...
First generation Sulfonylureas are more potent than second generation
...
Which of the following is not the first generation sulfonylurea
A) Glyburide
B) Glipizide
C) Glimperide
D) All of the choices
E) None of the choices
260
...
This drug has been highly effective against Schistoma mansoni
...
A) Praziquantel
B) Oxaminiquine
C) Ivermectin
D) Pyrantel
E) Mebendazole
262
...
It is
used as apamoate salt,which is quite insoluble and,as a result,is not readiy absorbed improving the usefulness of
the drug for the treatment of intestinal helminthes
...
A drug that belongs to a class of 16-membered macrocyclic lactones extracted from Streptomyces avermitilis
used in the treatment of various nematode infections
...
A)Praziquantel
B)Oxaminiquine
C)Ivermectin
D)Pyrantel
E)Mebendazole
264
...
The compound
has no activity against nematodes,but is highly effective against cestodes abd trematodes
...
Buspirone,a long chain arylpiperazine derivative,is an anxiolytic agent that is a partial agonist to
A)5HT1A receptor
B)5HT4 receptor
C)5HT3 receptor
D)5HT2A
E)5HT1D
266
...
A) 5HT1A receptor
B) 5HT4 receptor
C) 5HT3 receptor
D) 5HT2A
E) 5HT1D
For nos
...
Which of the givem reactions can be classified as Phase ll metabolism?
A)l,ll,lll,lV
B)l,ll only
C)lll,lV only
D)l,lll
E)ll,lV
269
...
Which of the following drugs would most likely undergo azoreduction
A)Chloramphenicol
B)Procaine
C)Lidocaine
D)Sulfasalazine
E)All of the above
271
...
Which of the following drugs would likely undergo amide hydrolysis
A)Chloramphenicol
B)Procaine
C)Lidocaine
D)Sulfasalazine
E)All of the above
273
...
It
produces a mercaptopuric acid derivative upon reaction with an electrophile
A)Glutathione conjugation
B)Acetylation
C)Methylation
D)Sulfate conjugation
E)Amino acid conjugation
274
...
Meperidine can undergo which of the following metabolic pathway?
I
...
Ester hydrolysis
III
...
N-dealkylation
A
...
I,II,III
C
...
I,III
E
...
Which of the following selective estrogen receptor modulators (SERMs) and antiestrogens has a
triphenylethylene structure used to treat early and advanced breast carcinoma in post menopausal women?
A
...
Fulvestrant
C
...
Clomiphene
E
...
Which of the following SERMs and antiestrogen is a benzothiophene derivative that has been approved for the
prevention and treatment of osteoporosis in menopausal women? It has antagonist properties on the endometrium
and breast tissue and agonist properties on bone and cardiovascular system?
A
...
Fulvestrant
C
...
Clomiphene
E
...
Which of the following SERMs and antiestrogen is an antagonist structurally on the estradiol structure which is
used in the treatment of women who have had disease progression after prior antiestrogen property?
A
...
Fulvestrant
C
...
Clomiphene
E
...
Which of the following drugs is not a nonsteroidal aromatase inhibitor?
A
...
Aminoglutethimide
C
...
A and B only
E
...
Which of the following drugs is a nonsteroidal aromatase inhibitor?
A
...
Aminoglutethimide
C
...
A and B only
E
...
An aromatase inhibitor used mainly in the treatment of cushing’s syndrome
A
...
Aminoglutethimide
C
...
A and B only
E
...
What is the probable mechanism of action of diuretic drug with the following structure?
A
...
B
...
It inhibits the Na+/Cl- symportar located in the distal convulated tubule
D
...
It inhibits sodium and water reabsorption by competitive inhibition of aldosterone
283
...
It increases intraluminal osmotic pressure, causing water to pass from the body into the tubules
...
It can induce dieresis by inhibiting the formation of carbonic acid within the proximal and tubular cells to limit the
number of hydrogen ions available to promote sodium reabsortion
C
...
It inhibits Na+/K=/Cl- transport system in the thick ascending limb loop of henle
E
...
What is the probable mechanism of action of a diuretic drug with the following structure?
A
...
B
...
It inhibits the Na+/Cl- symportar located in the distal convulated tubule
D
...
It inhibits sodium and water reabsorption by competitive inhibition of aldosterone
285
...
It increases intraluminal osmotic pressure, causing water to pass from the body into the tubules
...
It can induce dieresis by inhibiting the formation of carbonic acid within the proximal and tubular cells to limit the
number of hydrogen ions available to promote sodium reabsortion
C
...
It inhibits Na+/K=/Cl- transport system in the thick ascending limb loop of henle
E
...
Which of the following analgesic agent is 2 to 3 times more potent than morphine as analgesic and also known
as heroin?
A
...
Normorphine
C
...
Nalbuphine
E
...
Which of the following drugs represent a fragment of codeine’s structure, consisting of the phenyl and
cyclohexane rings? This drug possesses opioid activity but has other analgesic activity that is not reversed by
naloxone
...
Tramadol hydrochloride
B
...
Diphenoxylate
D
...
Diacetylmorphine Hydrochloride
288
...
Tramadol hydrochloride
B
...
Diphenoxylate
D
...
Diacetylmorphine Hydrochloride
289
...
A
...
Normorphine
C
...
Nalbuphine
E
...
This drug has a strong structural relationship to the meperidine type analgesics and has the ability to inhibit
excessive gastrointestinal motility
...
Tramadol hydrochloride
B
...
Diphenoxylate
D
...
Diacetylmorphine Hydrochloride
291
...
Rearrangement of amino acid residues at the N- and C- terminus at the B chain of insulin
B
...
From crystalline to amorphous)
C
...
Changing the site of injection
E
...
This is the only insulin analogue with a C14 fatty acid attached to an amino residue in the B chain of insulin
A
...
Aspart
C
...
Glargine
E
...
A highly purified protein containing 165 amino acids manufactured from a strain of E
...
This drug is used in patients 18 years or
older for treatment of hairy cell leukemia and chronic myelogenous leukemia
...
Roferon-A
B
...
Aldesleukin
D
...
Gemtuzumab Ozogamicin
294
...
coli containing a plasmid with alfa 2b gene
...
A
...
Interon
C
...
Rituximab
E
...
It is also known as interleukin 2 or T-cell growth factor
...
Roferon-A
B
...
Aldesleukin
D
...
Trastuzumab
296
...
Roferon-A
B
...
Aldesleukin
D
...
Gemtuzumab Ozogamicin
297
...
Roferon-A
B
...
Aldesleukin
D
...
Gemtuzumab Ozogamicin
298
...
A
...
vaccine
C
...
Intravenous immune globulin
E
...
A product derived from blood plasma of a donor pool similar to the IG pool but prepared so it is suitable for IV
use
...
A
...
vaccine
C
...
Intravenous immune globulin
E
...
A modified bacterial toxin that has been made non toxic but remains the ability to stimulate the formation of
antitoxin
...
Toxoid
B
...
Anti toxin
D
...
Immune globulin
Title: Pharmaceutical Organic Chemistry
Description: Pharmaceutical Organic Chemistry Questions and answers helpful for reviews and board exams.
Description: Pharmaceutical Organic Chemistry Questions and answers helpful for reviews and board exams.