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).