Download COLLEGE OF HEALTH SCIENCES

King Abdul-Aziz University
College of Health Sciences
Department of PHARMACY
Final Examination
Pharmaceutical Chemistry (HCHM 211)
Academic Year 1429-1430 (2009)
DATE: … February 14th, 2009………………….
STUDENT NAME: ………………………………………………….
INFORMATION TO CANDIDATES
1. NO OF PAGES: …7……
Time: 120 minutes
2. TOTAL NUMBER OF QUESTIONS:
…28… QUESTIONS
3. TOTAL NUMBER OF MARKS: …40.. MARKS (This constitutes 30
course marks)
% of your final
PLEASE READ THE QUESTIONS CAREFULLY & & ANSWER THE FOLLOWING
QUESTIONS IN THE ENCLOSED BOOKLET PROVIDED
THIS DOCUMENT CONSISTS OF …6… PRINTED PAGES EXCLUDING THIS PAGE
SECTION
A
B
C
D
TOTAL
MARKS
SIGN.
REVIEWED
SECTION A: (10 questions, each question 1 mark), please read the question
carefully and tick T (True) or F (False) as appropriate.
1.
Aminoglycosides are very polar cross BBB in meninges only
2.
T( ) F( )
Vitamin D deficiency results in rickets in infants and children as result of inadequate
calcification of bones.
T( ) F( )
PGE has a C=O at C-9 and -hydroxyl group at C-11 while PGF has two -hydroxyl group at
3.
C-9 and C-11.
T( ) F( )
4.
Vitamin D3 must be hydroxylated in the liver by vitamin to perform its action. T ( ) F ( )
5.
Vitamin B1 is very effective in cases of neuritis and in combination with vitamin C in
treatment of rheumatic conditions.
6.
T( ) F( )
Proinsulin is activated by an endopeptidase and carboxypeptidase to liberate equimolar
quantities of insulin and connecting C-peptide.
T( ) F( )
7.
Vitamin A is present mainly in fish liver, herbivorous liver, carrot and butter fat. T ( ) F ( )
8.
Ascorbic acid is involved in metabolic hydroxylation and drug metabolism. T ( ) F ( )
9.
Lypressin (8-Lys vasopressin) is more stable and more rapidly absorbed than vasopressin.
T( ) F( )
Misoprostol prevents gastric ulceration used orally but Dinoprost (PGF2) used parenterally
10.
for induction of labor or abortion within 1st trimester.
T( ) F( )
SECTION B: MCQs (9 questions, each question 1 mark)
The prodrug is prepared to …………………
11.
a.
Decrease the drug duration of action
( )
b.
Increase the drug potency
( )
c.
Increase the drug stability and bioavailability
( )
d.
Inactivate the drug at the desired target site of action
( )
Vitamin D accomplishes its biological role through …………………..
12.
a.
Enhancing the absorption of calcium and phosphate from small intestine
( )
b.
Promoting their mobilization from bone
( )
c.
Decreasing their excretion by the kidney
( )
d.
All of the above
( )
13.
The following are natural hormones except
a.
Prostaglandins
( )
b.
Insulin
( )
c.
Mestranol
( )
d.
Estradiol
( )
Page 2 of 7
14.
Lispro insulin is…
a.
Natural human insulin
( )
b.
Natural human insulin produced by r-DNA technique
( )
c.
More antigenic than porcine insulin
( )
d.
Less antigenic than other insulin products
( )
Vitamin K1 is the drug of choice as anti-hemorrhagic because ……
15.
a.
It can be activated in the body to more active metabolite
( )
b.
Rapid onset
( )
c.
Short duration of action
( )
d.
Vitamin K can be used to diagnosis kidney function accurately
( )
16.
The following statements about antiseptics are true except:
a.
The antibacterial potencies of primary alcohol increase with molecular weight up to C8,
where cutoff is reach
( )
b.
Branching decrease antibacterial potency, hence primary > 2ry > 3ry alcohol.
( )
c.
Substituted phenols are less potent, less irritant than unsubstituted one.
( )
d.
Cationic surfactants are inactivated by soap and not active against spore
( )
17.
Regarding to biological activity of folic acid, the following is true except:
a.
Reduced metabolically to tetrahydrofolic acid (THF).
( )
b.
Participate in the biosynthesis of nucleic acid
( )
c.
Its antagonists depends on N10 or N5 hydroxylation.
( )
d.
Biologically active as one carbon transfer.
( )
18.
Prostaglandins possess:
a.
Trans double bond at C13.
( )
b.
The hydroxy-bearing chain termed  chain and carboxy-bearing chain is -chain. ( )
c.
Two side chains are of the trans stereochemistry.
( )
d.
All of the above.
( )
Antifungal drugs ……
19.
a.
The more potent antifungal azoles possess two or three aromatic rings
b.
The nonpolar functionality give a high degree of lipophilicity to antifungal azoles. ( )
c.
all azoles are insoluble in water except fluconazole.
( )
d.
All of the above
( )
Page 3 of 7
( )
SECTION C:
Complete the missed information in the following questions:
(8 questions, each question 2 marks)
Streptomycin belongs to group of antibiotics named as ……………………………….
20.
Show on the structure the enzymatic inactivation (resistance)
H2N
NH2
HO
O
H2N
HO
HO
O
O
CH2NH2
HOH2C
O
HO
NH2
OH
21.
R 1 H 3C
Explain the SAR of tetracyclines
a.
…………………………………………………..…..…
b.
……………………………………………….…..…..…
OH
OH
O
N
R2
OH
OH
OH
O
CONH2
c.
…………………………………………………..…..…
d.
……………………………………………………..…………………..…..…
e.
…………………………………………………..…………………………..…..…
f.
…………………………………………………..…………………………..…..…
22.
Regarding macrolid antibiotics, complete the following:
a.
Erythromycin is acid labile when R = ………
N
O
R1 = ………………………………
b.
Erythromycin prodrug: R = …………
R1 = ………………………………
c.
RO
O
HO
R1O
HO
Acid-stable clarithromycin: R = …………
R1 = ………………………………
OCH3
O
OH
O
O
Page 4 of 7
O
O
O
23.
Discuss why acyclovir is antimetabolite drug?
N
HN
……………………………………....………………………
………..…………………………….……..………..…..…
H2 N
HO
N
N
O
………………………………………..…………………………
Acyclovir
……..………………………………………………………………………………………………
……………………………………………………………………………..………………..…..…
24.
Moxalactam is a third generation cephalosporin.
COOH
OCH3
H
N
O
CH3
O
N
HO
S
N
O
Moxalactam
a.
N
COOH
N
N
Illustate the role of the assigned groups on the pharmacological effect of moxalactam:
(OH) ………………………………………………………………………..………………
(COOH) ………………………………….…………………………………..………………
(OCH3) …………………………………..…………………………………..………………
(O) ……………………………………………………………………………..………………
b.
Using structural formula, explain how moxalactam can be given orally (prodrug)?
Page 5 of 7
25.
Examine the structure of the following compounds then complete the spaces
HO
H H
HO
H3C
S
N
O
NH2
N
H H
H3C
S
NH
NH
N
H
O
S
O
O
COOH
H2N
H
NH
N
O
COOH
N
SO3Na
Thienamycin
COOH
Imipenem
a.
Aztreonam sodium
Imipenem belongs to a group of antibiotic named as ………………………………,
ehile aztreonam belongs to ………………………………………group.
b.
Imipenem is structurally modified derivative of thienamycin, explain the reason of
this modification……………………………………………………………………….
………………………………………………………………………………………….
c.
In treatment of urinary tract infections, imipenem should coadminstred with
cilastatin in order to ……………………………………….………………………..
26.
Danazol is oral androgen.
CH3
OH
C
CH
CH3
N
Danazol
O
a.
It considered as androgen because ……………………… in its structure, orally due to
…………………………………………….
b.
The increase in anabolic properties over androgenic is due to ………………………
…………………………………………………..
27.
Cyclophosphamide is anticancer prodrug, discuss the mechanism of action?
H
N
Cl
O
P
N
O
Cl
Page 6 of 7
SECTION D:
28.
Fill the spaces in the table by the corresponding compound name (5 marks)
OCH3
O
OCOCH3
CH3
H 3CO
OH
C
CH
H
Cl
O
CH3
H3CO
O
Medroxyprogesterone acetate Norethindrone
Chlorotrianisine
C2H5
OCH2CH2N
C2H 5
H 3C
N
NH2
H 2N
CH3
OH
N
2 Cl
HOH2C
CH3
Tamoxefen
OH
Vitamin B1
Ascorbic acid
CH 2OH
OH
CH3
O
HO
C CH
CH3
CH3
F
N
O
O
Mestranol
OH
CH3
O
O
H3CO
Triamicinolone acetonide
Biological activity
Danazol
Compound name
Semisynthetic anabolic androgen
Progesterone prodrug
Orally active non-steroidal estrogen
Nor-testosterone with progesterone activity
Anti-estrogen
Anti- scurvy drug
Anti-inflammatory steroidal prodrug
Orally active steroidal estrogen
anti-beriberi factor
BEST WISHES
Dr. M. Sheha
Page 7 of 7
O
O
C
CH