Classification of Penicillins

1. CLASSIFICATION OF PENICILLINS
N
S
OR
2
O
H
R
3
N
H
R
1
O
O
Drugs R1 R2 R3
Natural penicillins
Penicillin G (Benzyl penicillin) H H
Penicillin F
H
H
C
H3
H H
Penicillin K C
H3 H H
Penicillin N
O
H
NH2
O H H
Penicillin O S
C
H2 H H
Penicillin X
O
H
H H
Semisynthetic penicillins
Acid resistant penicillins
Penicillin V
O
H H
Phenethicillin
O
CH3 H H
Propicillin
O
CH3 H H
Penicillinase resistant penicillins
Oxacillin
O
N
C
H3
H H
Cloxacillin
O
N
C
H3
Cl H H

2. Dicloxacillin
O
N
C
H3
Cl
Cl H H
Flucloxacillin
O
N
C
H3
Cl
F
H H
Methicillin
O
N
C
H3
O
C
H3
O CH3
H H
Nafcillin O CH3 H H
Extended spectrum penicillins
Aminopenicillins
Ampicillin NH2 H H
Amoxycillin NH2
O
H
H H
Epicillin NH2 H H
Bacampicillin NH2
O O CH3
CH3 O H
Pivampicillin NH2
O CH3
O
CH3
CH3
H
Carboxypenicillins
Carbenicillin O OH H H

3. Carfecillin
O O
H H
Carindacillin
O O
H H
Ticarcillin O OH
S
H H
Temocillin O OH
S
H OCH3
Ureidopenicillins
Azlocillin
NH
O
N
NH
O
H H
Mezlocillin
NH
O
N
N
O
S
O
O
CH3 H H
Piperacillin
NH
O
N
N
CH3
O
O
H H
Amidinopenicillins

4. Mecillinam
N
S
OH
O
H
H
N
O
N
H
Pivmecillinam
N
S
O
O
H
H
N
O
N
H
O
O
CH3
CH3
CH3