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Selected Synthetic drugs

Analgesics and anti-pyretics
• Analgesics are drugs used for relieving pain while
maintaining consciousness
...

• Drugs for these two effects include prescription and
over the counter (OTC) drugs
...

• Most synthetic analgesics aspirin, paracetamol, and
phenacetin are mainly used to relieve headaches,
muscular and athritic pains
...


Aspirin, paracetamol, phenacetin

Acetyl salicylic acid (aspirin)
• Aspirin is an analgesic, antipyretic which is highly
popular
...

• It is marketed as the Na salt or as mixture with
carbonate buffer
...


Synthesis of aspirin- Kolbe-Schmidt
synthesis

Paracetamol, (Acetominophen,
Tylenol)
• Other competing analgesics are acetaminophen, ibuprofen,
acetophenetidene (phenacetin)
...
It is anti-pyretic and is made from
para-amino phenol by selective acetylation of the amine
...

• It has analgesic and anti-inflammatory action
...
H2/P d/C

2
...

It does not have any anti-pyretic effect
...

• It is usually administered as the amine
hydrochloride
...

• Its synthesis involves a Mannich reaction
followed by Grignard addition on the ketone
...

(cough suppressant)
• It is found in opium in low concentrations
...

• It is also starting material for hydrocodone
which is a significant pain reliever and
antitusive
...


Codeine
H
C
O
3
H
O
O
O
H
H
O
M
o
rp
h
in
e

H

H
3
NC

H

H

H
3
NC

H
O
C
od
ein
e
H
O
3C

O

H
N

H
O

H
ydrocodone

C
H
3

Morphine alkaloids assessment of
function
• The most useful property of morphine and
derivatives is their depressant action, which
provides a heightened tolerance to pain,
drowsiness and reduced perception to the
external environment
...

• Heroin is obtained by diacetylation of morphine
...


Heroin
HO

O

O

H
N

H

CH3

O

O

N

H

HO

O

M orp h in e

M
orphine

O

H

Heroin

CH3

Anti-bacterial agents
• Anti-bacterial agents are used to control
bacterial infections such as pneumonia, TB
and urinary track infections
...

• Examples include penicillins, tetracyclines
and sulphonilamides
...

N
H
2
1
...
R
N
H
2
2
...
H
2O

SO
l
2C

SO
H
R
2N

Sulphonilam
ide

p-Aminobenzoic acid (PABA)
• Sulphonamides are bacteriostatic agents and
serve by mimicking p-aminobenzoic acid
which is necessary in regulating development
of bacterial cell walls
...

• Both drugs are used in the treatment of ear
and urinary tract infections
...

• Over 90% of the cases and 98% of deaths occur in
developing countries mostly Africa
...

• The number of cases and strains of TB which are resistant
to the first –line drugs have increased
...

• HIV positive patients are 30-50% more likely to develop
active TB
...


TB drugs
• Streptomycin was the first drug against TB but
its short-comings led to development of other
anti-biotics in the 1950s
...

• The full treatment takes six to 9 months
...


Isoniazid synthesis
N(
O
)

N

C
H
3

C
O
O
H

M
e
t
h
y
l
p
y
r
i
d
i
n
e

I
s
o
n
i
c
o
t
i
n
e
a
c
i
d

N

H
N
H
N
C
2
O
I
s
o
n
i
a
z
i
d

Ethambutol, Rifampicin, Pyrizinamide

H
O
O
H
O
H
O
N
H
l
to
u
b
m
a
th
E

H
N

O
H

O
N
H
N
2

O O
HO
HO
O
H
N
O
O

H
O
O
in
ic
p
m
ifa
R

N

N
e
id
m
a
in
z
a
r
y
P

N

State of TB drugs
• Due to the fact that there is little interest by
western pharmaceutical companies to
develop drugs for the disease there is lack of
drugs for this condition
...
These
drugs are at various stages of development
...
It is
synthesized from 5-nitrofurfural in the
manner shown
...

• They include hypnotics, sedatives, tranquilizers, stimulants,
antidepressants and anti-convulsants
...

• Sedatives cause calming effect on nerves without inducing
sleep
...

• Anticonvulsants control epileptic seizures
...


Seritraline
• This is a leading anti-depressant and is
marketed as Zoloft
...
It prevents the nerve
hormone serotonin transportation to nerve
endings
...
It is also
prescribed for obesity
...
H
B
r
C
O
E
t
2
2

...
C
H
3
N
H
2
,T
i
C
L
4

1

...
A
l
C
l
3

2

...

• They depress the activities of many systems
of the body such as the CNS, hence induce
deep sleep in addition to depressing
respiration
...


Synthesis of barbiturates
• They are made by the reaction of urea with a
suitable derivatives of diethyl malonates
...
N
a
C
N

2

...
E
tO
2

...

•
H
O

N

N

C
H
3
N

N

O
N
2
O
H
C
3

M
e
th
a
q
u
o
lo
n
e

P
h
N
itr
o
z
e
p
a
m

Benzodiazepines
• Other than barbiturates the other drugs that
relieve pain and nervous tension without
impairing consciousness (tranquilizers) are
benzodiazepines such as diazepam (Valium)
and chlorodiazepoxide (Librium)

H
C
3
O
N
H
C
H
N
3
N

N
C
l
+
N
C
l
P
h
O
P
h
D
i
a
z
e
p
a
m

C
h
l
o
d
i
a
z
e
p
o
x
i
d
e
(
V
a
l
i
u
m
)
(
L
i
b
r
u
m
)

Synthesis of diazepam
N
H
2

• D

N
H
O
2

A
l
C
l
C
l
3

P
h

O
P
h
+

C
l

C
l
H
C
3
N
H
O
N
M
e
S
O
P
h
P
h

N
H
O
N
2

N
H
O
H
2

24

K
C
O
2
3

C
l
O
C
l
C
l

C
l
C
H
C
O
C
l
2
H
C
3

N
H
O
N
P
h

C
l
O

O

+
O
H
N
N
N
H
/
P
d
/
C
N
P
h
P
h
2

D
i
a
z
e
p
e
m

C
l

C
l

Other anti-depressants
• Flouxetin (prozac) and paroxetin are recently
introduced fluorinated anti-depressants which are
used in depressions, obesity, alcoholism and
anorexia
...

F3C

O
CH CH2CH2NHCH3

Fluoxatine (Prozac)

F
CH
O 2
Paroxetin

O

O

Anti-convulsants
• These drugs are used for control of epileptic
seizures
...
It is
synthsised thus:
O

C H O

O H

O

N aC N

H N O

O

3
B e n z il

B e n z ilic a c id r e -a r r a n g e m e n t

H 2N
H 2N

H O
C O O E t

O

O
C N H
C
N
H O
5 ,5 -D ip h e n y lh y d a n to in

Diuretics
• The diuretics decrease body fluids by increasing
the excretion of urine by the kidneys
...

• Furesamine is a typical diuretic
...


Furesamine synthesis
C l

C l

C O O H

C lS O 3 H

N H

C l

C l
S O 2C l
O

C l

C O O H

C O O H

3

C l
S O 2N H

C H 2 N H O2
H 2C

N H
C O O H
F u r e s a m in e

C l
S O 2N H

2

2

Anti-hypertensives
• The anti-hypertensives agents lower blood pressure
...
The other antihypertensive is reserpine
...

O H
C H

O
H 2C

N
H

O

3

C H

O H
H N

3

CH
C H

NH

P r o p r a n o lo l

O
A te n o lo l

2

3

3

Synthesis of Propranolol

C
l
O
H

O

O

O
H
2N

a-naphthol

O

O
H

N
H
H
H
3C C
3
P
ropranolol



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