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Classification of Cephalosporins.docx

Classification of cephalosporins

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CLASSIFICATION OF CEPHALOSPORINS
N
H
R
3
N
H
R
1
O
O
S
R
2
O
O
H
Drug R1 R2 R3
First generation
Cephalothin
(Cefalotin) S
O CH3
O
H
Cephaloridine
S N
+
H
Cefalexin NH2 CH3 H
Cefradine NH2 CH3 H
Cefadroxil NH2
O
H
CH3 H
Cefatrizine NH2
O
H
S
N
NH
N
H
Cefazolin N
N
N
N
S N
S
N
H
Second generation
Cefaclor NH2 Cl H
Cefprozil NH2
O
H
CH3
H
Cefamandole
O
O
H
S N
N
N
N
C
H3
H
Cefuroxime
N
O
O
CH3
O
O
NH2 H
Cephamycin C O
O
H
NH2
O
O
NH2 OCH3
Cefoxitin S O
O
NH2 OCH3
Cefotetan O
O
H
N
H2
O
S N
N
N
N
OCH3
Cefmetazole S
N
S N
N
N
N
OCH3
Third generation
Cefotaxime
N
S
N
O
CH3
N
H2
O
O
CH3 H
Ceftriaxone
N
S
N
O
CH3
N
H2
S N
N
C
H3
O
O
H
H
Cefixime
N
S
N
H2
O OH CH2 H
Cefoperazine
NH
O
H
N
O
N O
O
CH3
S N
N
N
N
CH3 H
Ceftibuten
N
S
N
H2
O OH H H
Ceftazidine
N
S
N
O
N
H2
OH
O
N
+
H
Fourth generation
Cefepime
N
S
N
O
N
H2
CH3
N
+
CH3
H
Cefpirome
N
S
N
O
N
H2
CH3
N
+
H
Cefiderocol
N
S
N
O
N
H2
OH
O
N
+
N
H
Cl
OH
OH
O H
Fifth generation
Ceftobiprole
NH
N
S
N
O
N
H2
N
O
NH
H
Ceftaroline N
O CH3
N
N
S
NH
P
O
O
H
OH
S
N
N
+
CH3
H
Ceftozolone
N
N
S
N
O
N
H2
OH
O
N
+
N
C
H3
NH2
NH
NH
O
NH2 H

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Classification of Cephalosporins.docx

  • 1. CLASSIFICATION OF CEPHALOSPORINS N H R 3 N H R 1 O O S R 2 O O H Drug R1 R2 R3 First generation Cephalothin (Cefalotin) S O CH3 O H Cephaloridine S N + H Cefalexin NH2 CH3 H Cefradine NH2 CH3 H Cefadroxil NH2 O H CH3 H Cefatrizine NH2 O H S N NH N H Cefazolin N N N N S N S N H Second generation Cefaclor NH2 Cl H Cefprozil NH2 O H CH3 H Cefamandole O O H S N N N N C H3 H
  • 2. Cefuroxime N O O CH3 O O NH2 H Cephamycin C O O H NH2 O O NH2 OCH3 Cefoxitin S O O NH2 OCH3 Cefotetan O O H N H2 O S N N N N OCH3 Cefmetazole S N S N N N N OCH3 Third generation Cefotaxime N S N O CH3 N H2 O O CH3 H Ceftriaxone N S N O CH3 N H2 S N N C H3 O O H H Cefixime N S N H2 O OH CH2 H Cefoperazine NH O H N O N O O CH3 S N N N N CH3 H
  • 3. Ceftibuten N S N H2 O OH H H Ceftazidine N S N O N H2 OH O N + H Fourth generation Cefepime N S N O N H2 CH3 N + CH3 H Cefpirome N S N O N H2 CH3 N + H Cefiderocol N S N O N H2 OH O N + N H Cl OH OH O H Fifth generation Ceftobiprole NH N S N O N H2 N O NH H Ceftaroline N O CH3 N N S NH P O O H OH S N N + CH3 H