Medical Microbiology

ThePrinciplesofAntibioticTherapy 195

BasicChemicalStructuresoftheMostImportantAnti-infectives

a Betalactam antibiotics

Penicillins Cephalosporins Monobactams

Oxapenams

(clavulanic acid)

Carbapenems

(thienamycin)

Oxacephems

(flomoxef)

Carbacephems

(loracarbef)

tobramycin

b Aminoglycosides c Tetracyclines

e 4-Quinolones f Sulfonamides

sulfanilamide

d Lincosamides

clindamycin

N

HN S

O

COOH

R^2

R^1

12 3

4

5

76

8

N

O

O COOH

OH

N

C

O COOH

N

O

O

COOH

N

O

C

COOH

N

R^1 R^2 R^3 R^4

OH

CO

OH O OH O

H 3 C CH 3

NH 2

7 6 5

N

HN

N

F

O

COOH

1

6

7

OS

CH 3

OH

OH

HO

CH

CH

CH 3

C

C N

N O H

CH 3

C 3 H 7

Betalactamase

CH 3

CH 3

COOH

H

R HN

6

7

5

1

2

3

4

N

H 2 N

O SO 3 H

2 1

4 3

SO 2

NH

H 2 N

ciprofloxacin H 2 N COOH

O

OH NH 2

HO

O

NH 2

NH 2

NH 2

O

OH

O

HO

HO

NH 2

OH

5

4

3 2

1

4'5'^6

3' 2'

1'

6'

4''

5''

6''

N

S

O

2

1''

3'' 2''

4

Sulfonamides are

antagonists of

p-aminobenzoic acid

Fig.3. 29 Antibioticgroupsoftenincludemanydrugsubstanceswithdifferent

substituents.

3

Kayser, Medical Microbiology © 2005 Thieme