2.3 Mekanisme Reaksi Diklofenak Ibuprofen dan Ketoprofen a. Diklofenak
NH Cl
Cl C
O Cl
C O Cl
NH
+
Cl Cl
C O
Cl
-
O
-
Cl
-HCl
N Cl
Cl O
O Cl
REAGEN -
δ
Al
Cl Cl
Cl
N Cl
Cl O
O
δ δ
δ δ
δ
- +
- +
- H
H
N Cl
Cl CH
O OH
N Cl
Cl H
2
C O
H2 -H2O
HOH
DALAM BASA
NH Cl
Cl H
2
C C
O OH
DIKLOOFENAK
Universitas Sumatera Utara
b. Ibuprofen
O
H N
O O
S
O OH
O
H
S
O O
O OH
- H
+
N O
O N
O O
+ -
H -
OH
HO
H
2
C CH
CH
3
CH
3
H
2
C CH
H
3
C H
3
C
NO
2
Zn+ HCl o
N N
OH H
+ HO H
- N
N+
N N
+
-
-
H
2
C CH
H
3
C H
3
C H
2
C CH
H
3
C H
3
C
H
2
C CH
H
3
C H
3
C
CH
2
CO OC
2
H
5
CO OC
2
H
5
H
2
C CH
H
3
C H
3
C CH
CO OC
2
H
5
CO OC
2
H
5
CH3I
-HI
a. Ketoprofen
H 2
C C
H H
3 C
H 3
C C
C O
O C
2 H
5 C
O O
C 2
H 5
C H
3 H
3 O
+ -
C O
2 -
C 2
H 5
O H
H 2
C C
H H
3 C
H 3
C C
H C
O O
C 2
H 5
C H
3 +
H +
+ H
2 O
- C
2 H
5 O
H H
2 C
C H
H 3
C H
3 C
C H
C O
O H
C H
3
Universitas Sumatera Utara
.
N O
OH + H+
N O
OH H
+ - H2O
N O
+ N
H H
N O
+ NUKLEOPILIK
ELEKTROPILIK LAMBAT
O
H N
O O
S
O OH
O
H
S
O O
O OH
- H
+
N O
O N
O O
+ -
H -
OH
HO
H
2
C CH CH
3
CH
3
NO
2
Zn+ HCl C
O KE META
C O
N H
H N
O +
-H+ N
H N
O CEPAT
PROTONS REARR N
N OH
H +
N N
OH H
+ HOH
- N
N+
-
-
C O
C O
C O
C O
C O
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3 H
C C
O S
C o
A -
A T
P C
O O -
H O C H
C H H
2 C
S C H
N H H N
O
C H 2
4 C O O H
+ +
C H C H
H 2
C S
C H N
H N O
C H 2
4 C O O H
C O O -
B I
O T
I N
E N
Z I
M B
I O
T I
N -
C O
O -
A D P + P i E
N Z
I M
B I
O T
I N
H 2
C C
O S
C o
A -
- O O C M
A L
O N
I L
- C
O A
N N
+
CH
2
COOC
2
H
5
COOC
2
H
5
CH COOC
2
H
5
COOC
2
H
5
CH3I
-HI
C COOC
2
H
5
COOC
2
H
5
CH
3
H3O+ -CO2
-C2H5OH
C H
COOC
2
H
5
CH
3
+ H+ + H2O
-C2H5OH
C H
COOH
CH
3
C O
C O
C O
C O
C O
KETOPROFEN
2.4 Sintesis Prostaglandin
H S
C H
2
C H
2
N H
C O
C H
2
C H
N H
2
C O
C H
O H
C C
H
3
C H
3
C H
2
O P
O
-
C H
2
O
H H
H
O O
H P
O H
O O
-
H N
N N
N N
H
2
C O
E N
Z Y
M A
Universitas Sumatera Utara
O S
9 1
2
O 2
+ N
A D
H +
H +
H 2
O +
N A
D +
K o A
O S
K o A
9 1
2
9 1
2 6
6 S
A T
U R
A S
I L
I N
O L
E I
L -
K O
E N
Z I
M A
- O
K T
A D
E K
A D
I O
N I
L -
K o
A
g L
I N
O L
E I
L -
K O
E N
Z I
M A
- O
K T
A D
E K
A T
R I
O N
I L
- K
o A
6 9
1 2
2 H
C COOH
C O
S- Ko
A M
E L
O N
I L
- K
o A
C 2
1 8
1 8
1 1
1 4
8 2
C O
S K o A
S I
S T
E M
E L
O N
G A
S E
R A
N Y
A I
M I
K R
O S
O M
A L
E L
O N
G A
S E
O 2
+ N
A D
H +
H +
H 2
O +
N A
D +
5 S
A T
U R
A S
I
1 1
1 4
8 2
C O
S KoA
5
D I
H O
M O
- g
- L
I N
O L
E I
L -
K O
A E
L K
O S
A T
R I
O L
- K
o A
8 1
1 1
4
A R
A K
I D
O N
I L
- K
o A
- E
I K
O S
A T
E T
R A
E N
O I
L -
K o
A 5
8 1
1 1
4
Universitas Sumatera Utara
PERU BAH AN ARAK H I DON AT
ASPI RI N I NDOMETASI N
I BUBRUFEN
O OH
1 2
3 4
5 6
7 8
9 10
11 _
13 14
15
δ δ
δ δ
δ δ
δ δ
δ δ
- -
- -
- +
+ +
+ +
+
δ δ
δ
- 12
O
O O
OH
O OH
1 11
2 3
4 5
6 7
8 9
12 13
14 15
16 10
O O
1 2
3 4
5 6
7 8
9 10
11 12
13 14
15 16
CH CH
2
O C
H
2
C O
CH
2
nCH
3
O P
O O
-
RO
FOSFOLIPID-ESTER ARACHIDONAT
ARACHIDONAT AA FOSFOLIPASE
A2
12-HIDROPEROXYARACHIDONAT 12-HPAA
12-HIROKSIARACIDONAT=12HAA 2O2 AA SIKLOOKSIGENASE
OH O
OOH O
O
PROSTAGLANDIN ENDOPEOCID H2 G2 {PGH2{PGG2}]
PROSTASIKLIN SINTESIS
DENGAN PENATAAN ULANG
O COOH
HO OH
PROSTASIKLIN PGI2
HO HO
COOH
OH O
6-KETO-PGF14
O O
OH COOH
DENGAN PENATAAN ULANG
TROMBOKSAN SINTESIS
TROMBOKSAN A TXA2
PENATAAN ULANG
O COOH
HO OH
TROMBOXAN B2 TXB2
? ?
DENGAN PENATAAN ULANG
TROMBOKSAN SINTESIS
ANTAGONI S TROMBOKSAN
Universitas Sumatera Utara
OH O
OOH
+ 2HC
C C
O O
H
H
HYROXHEPTADECATRIONIKACID HHT
MALONALDEHID 1. SINTESIS PGE2
2. SINTESIS PGD2 3. SINTESIS PGF 2
OH O
OOH O
O
1. PGE2 ; R1=O, R2 = α OH, H
2. PGD2 ; R1 = α OH, H, R2 = O
3. PGF2; R1 = R2 = αΟΗ, Η
2.3 Sifat Kimia Fisika dan Aktivitas Biologis
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