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Title: Pharmaceutical Organic Chemistry
Description: Pharmaceutical Organic Chemistry questions and answers helpful for review and practice of exams and board exam.
Description: Pharmaceutical Organic Chemistry questions and answers helpful for review and practice of exams and board exam.
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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
...
Ce
been replaced by sulphur?
a
...
c
...
e
...
The only guanosine analogue that is used against HIV infections and Hepatitis B
...
b
...
d
...
Zidovudine
Didanosine
Lamivudine
Abacavir
Efavirenz
98
...
a
...
c
...
e
...
Which of the following statements is/are correct regarding anti-HIV drugs?
a
...
c
...
e
...
NNRTIs act as enzyme inhibitors by binding to an allosteric binding site
...
Below is the structure of chloramphenicol, a bacteriostatic agent that binds to the 50s subunit of
ribosome
...
b
...
d
...
The nitro group
The 2 alcohol groups
The dichloroacetamide group
A and B only
All of the above
101
...
b
...
d
...
The nitro group
The 2 alcohol groups
The dichloroacetamide group
The aromatic ring
A and B only
102
...
II
...
IV
...
b
...
d
...
103
...
The ketone and 2 alcohol groups in its structure are responsible for its acid sensitivity
...
I, II, III, IV
I, III, IV
I, II, IV
II, III
III, IV
Amantadine is one of the earliest antiviral drugs used clinically against flu
...
Amantadine is an adamantine related to rimantadine
...
It inhibits the penetration and uncoating of the influenza virus
...
It can inhibit replication of the influenza virus by blocking a viral ion channel
called matrix (M2) protein
IV
...
a
...
c
...
e
...
104-107, please refer to the structures below:
104
...
b
...
d
...
Structure I
Structure II
Structure III
Structure IV
II and III
105
...
b
...
d
...
Structure I
Structure II
Structure III
Structure IV
II and III
106
...
b
...
d
...
Structure I
Structure II
Structure III
Structure IV
II and III
107
...
b
...
d
...
Structure I
Structure II
Structure III
Structure IV
II and III
108
...
a
...
c
...
e
...
An antisense drug designed to inhibit the mRNA molecules that code for proteins which
suppress apoptosis
...
b
...
d
...
Oblimersen
Calicheamicin
Carboplatin
Irinotecan
Cyclophosphamide
110
...
Its reaction with
DNA ultimately leads to cutting of the DNA chains
...
b
...
d
...
Oblimersen
Calicheamicin
Carboplatin
Irinotecan
Cyclophosphamide
111
...
a
...
c
...
e
...
An alkylating agent that can cause intrastrand cross-linking preferref over cisplatin for the
intravenous treatment of advanced ovarian tumors because of its less severe side effects
...
b
...
d
...
Carboplatin
Irinotecan
Cyclophosphamide
113
...
b
...
d
...
Carmustine
Busulfan
Procarbazine
Mitomycin C
None of the choices
114
...
a
...
c
...
e
...
An antimetabolite that is very similar in structure to the natural folates differing only in additional
amino and methyl groups
...
a
...
c
...
e
...
This drug acts as a prodrug for a suicide inhibitor
...
a
...
c
...
e
...
An anti-leukemia drug isolated from Streptomyces antibioticus and is a powerful inhibitor of
Adenosine deaminase
...
b
...
d
...
Methotrexate
5-fluorouracil
6-mercaptopurine
Pentostatin
Cytarabine
118
...
a
...
c
...
e
...
Which of the following pairs is correctly matched?
I
...
III
...
a
...
c
...
e
...
A decapeptide analogue of the luteinizing hormone – releasing hormone designed to be more
resistant to peptidase degradation
...
b
...
d
...
Goserelin
Raloxifene
Cyproterone acetate
Anastrazole
4-hydroxyandrostenedione
121
...
a
...
c
...
e
...
This mode of therapy involves an antibody which has catalytic activity designed to activate a
prodrug
...
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
123
...
a
...
c
...
e
...
This involves irradiation of tumors containing porphyrin photosensitizers resulting to the
production of reactive oxygen species which are fatal to the 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
125
...
Once the antibody has become attached to the outer surface of cancer cells, a prodrug is
administered which is activated by the enzyme at the tumor site
...
b
...
d
...
Antibody-directed enzyme prodrug therapy (ADEPT)
Antibody-directed abzyme prodrug therapy (ADAPT)
Gene -directed enzyme prodrug therapy (GDEPT)
Photodynamic
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
...
Ch
Title: Pharmaceutical Organic Chemistry
Description: Pharmaceutical Organic Chemistry questions and answers helpful for review and practice of exams and board exam.
Description: Pharmaceutical Organic Chemistry questions and answers helpful for review and practice of exams and board exam.