Biomedical Engineering Reference
In-Depth Information
HO
O
H 2 N
R 4
H 3 C
H 3 CHN
O
R
OH
HO
R:
O
O
CH 3
H
NH 2
H 2 N
C 1
C
C 1a
C
H
H
NHCH 3
NH 2
Gentamicin
CH 3
H
C
C 2a
C 2
C
H
CH 3
NH 2
NH 2
OH
O
H 2 N
H 3 C
CH 3 NH
O
NH 2
OH
HO
R 3
O
O
H
Sisomicin
NH 2
R 3 HN
C 2 H 5
Netilmicin
FIGURE 25.12
Gentamicin and derivatives.
HO
H
NHCH 3
H
OH
H
H
O
CH 3 HN
HO
H
H
O
H
O
O
H
Spectinomycin
H
H
CH 3
R 1
R 2
NO 2
H
Chloramphenicol
NHCOCHCl 2
NO 2
CO(CH 2 ) 14 CH 3
Palmitate
R 1
CH
CH
CH 2
OR 2
NO 2
CO(CH 2 ) 2 COONa
Hemisuccinate
H
Thiamphenicol
SO 2 CH 3
OH
SO 2 CH 3
COCH 2 NH 2 .HCl
Glycinate
FIGURE 25.13
Spectinomycin, chloramphenicol, and thiamphenicol.
Gentamicin contains fewer groups that may react with these enzymes. The introduction of the
2-hydroxy-4-amino group in amikacin protects many groups against these enzymes, while main-
taining the activity of the parent molecule. Tobramycin, which was obtained from Streptomyces
tenebrarius in 1968, is also less susceptible because one hydroxy group is replaced by hydrogen.
A special product is spectinomycin, which was isolated in 1961 from Streptomyces spectabilis .
It is a broad-spectrum antibiotic with a moderate activity. It is used for the treatment of gonorrhea
(Figure 25.13).
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