O

O
S

R - C - NH

CH3
CH3

R2 -C - NH

S
N

R1

CH2 - O - Ac
C

OH

OH
S

R - NH
O

H2N

CH3
CH3

N
C

H3C

HS

CH2OH

OH

CH3

COOH H2N

H2N

COOH

OH

COOH
HS - CH2 - CH - NH2

HOOC - CH2 - C6H5

COOH

HS - CH2 - CH - NH - C - CH2 - C6H5

H5C6 - CH2 - C - NH - CH

CH3
CH3

C - NH - C - COOH
O

CH - CH

NH2
COOH

H2O
O

SH

CH2

H3C
H3C

H2O

H5C6 - CH2 - C - NH
O

N
C

CH3
CH3
O
OH

.
1

CH3
CH3
COOH

R-C-N
N

O O

[OH - ]
H

R-C-N
O

C N
H
OH

t0

R - C - HN - CH2

CO2

N
H

CH3
CH3
COOH

HgCl2
CH3
CH3

HS
H2N

CH3
CH3
COOH

CH

R - C - NH - CH - C

R - C - NH - CH2 - C

COOH

COOH

O
CO2

O
H

R - C - NH - CH2 - C

O
H

CH3
CH3

HS
+
H2N

CH

R - C - HN - CH2

COOH

N
H

Benzylpenicillinum-natrium
Benzilpenicilin sodic

CH3
CH3
COOH

Benzylpenicillinum-kalium
Benzilpenicilin potasic

CH3
CH3
C

CH2 - C - NH
N

O
ONa

(OK)

Benzylpenicillinum-procainum
Benzilpenicilin procain
NH2

O
S

CH2 - C - NH
N

CH3
CH3
C

O
O-

. H2O
+ C2H5
C - O - C2H4 - N
C2H5
H
O

Phenoxymethylpenicillinum
Fenoximetilhenicilin
O
S

O - CH2 - C - NH
O

CH3
CH3
C

O
OH

Benzylpenicillinum benzatinum
Benzatin benzilpenicilin (Bicillin-1)
O

CH3

CH2 - C - NH

CH3
C

O
O

H H

H H

CH2 - N - C2H4 - N - CH2

.
2

Ampicillinum trihydratum
Ampicilin trihidrat
O

NH2

CH3
CH3
C

CH - C - NH
N

. 3 H2O

O
OH

Oxacillinum natrium
Oxacilin sodic
O

CH3

CH3
CH3
C

C - NH
N

H2O

ONa

Carbenicillinum natrium
Carbenicilin disodic
O
S

CH - C - NH
C
O

ONa

CH3
CH3
C

CH - C - NH
NH2

ONa

NH

OH

Azlocillinum natrium
Azlocilin sodic

C
N

O
NH

. 3 H2O

CH - C - NH
O

Amoxicillinum
Amoxicilin

O
HO

CH3
CH3
C

CH3
CH3
C

O
ONa

R
H
N

R
O

CH3
CH3

NH2OH
HO

NaOH

O
H
N

N H
S
O HN

COOH

COOH
2+

3+

H3C
H3C

Fe

Cu

R
H

CH3
CH3

NH
NH O

Cu

O HN

HOOC
O

COOH

N
H
O

CH3
CH3

O
H
N

Fe/3

H
S

CH3
CH3

O HN

COOH

N
R

H COOH
S

CH3
CH3
COOH

HCl

CH3
CH3 . HCl
COOH

H2SO4 conc.

O - CH2 - C - OH

H COOH
S

OH + HO - CH2 - C - OH

O
[O]

HO - CH2 - C - OH

SO3H
HO

H C H

CO2 + H2O

H
C
O

HO3S
+

OH
OH

HO
SO3H

HO3S

H2SO4 cont.
- H2O

SO3H
HO

SO3H HO3S

HO3S
CH2

OH

HO

OH

HO3S

SO3H

CH3
CH3
C

O - CH2 - C - NH
N

H2SO4
O

H
C

OH

O - CH2 - C - OH

OH

O
OH + CH3 - C - OH

OH

H2SO4 cont.
H2O

[O]

HO

H2SO4 cont.

OH

H C H
H +

CH3
CH3
C

H2N

H2SO4

O - CH2 - C - OH

HO

HO3S

SO3H

HO

OH

HO

CH

HO

[O]

C
H

2H

H
N
O

S
N

CH3
CH3
COOH

[OH - ]

N H

NaO
O

CH3
CH35
COONa

[H + ]

COOH

H2N

I2

COOH

HO3S
H2N

CH3
CH3

H
N
O

COOH

COOH

CH2 - CH3

CH3
CH3

CH3
CH3

COOH

CH3
CH3

3 I2

H
N
O

HS

COO -

N
CH2 - CH3

R
H
N

R
O

S
N

NH2

O
CH3
CH3

2 NaOH

NaO
O HN

COONa

CH - COOH + HC

N H

O
H

CH3
CH3

N = CH
COONa
2
CH - COOH

+ HO
2

N = CH2

N = CH2

CH - COOH

H
N

R
O

+ HO
2

CH3
CH3

COOH

CH - COONa

NaOH

SH

H
N

CH3
CH3
COOH

H2N

CH3
CH3

5 1
4
2
N 3

6
7

R1 - HN

COOH

6
5

7
8

1 2

H2N

7-a
(7-)

HOOC - CH - (CH2)3 - CO - HN

CH3
O

7-

(7-)
S

A
CH2 - O - C - CH3
C

OH

+
N
H

OH

OH

NH2

CH2 - O - C - CH3

R2

OH

H2N

HOOC

6-
7

H2N
O

S
B

A
CH2 - O - C - CH3
C

OH

7-
H

NH2
HOOC - CH - (CH2)3 - CO - HN

S
A

NaOCl

CH2 - O - C - CH3
O

HCOOH

OH

H
N
O

HOOC

+ H2O

A
-

CH2 - O - C - CH3
O

O
O

HOOC

OH

H
H2N

7-

CH2 - O - C - CH3
O

OH

7-:
H
N

R
O

S
N

[O]

CH3
CH3

H
N

R
O

S
N

COOH

CH3
CH3
COOH

OH

H
N

R
O

S
N

H
N

CH2

CH3

S
O

N
COOH

7-

CH3
O

CH3

S
N

CH2 - C - Cl

CH3
COOH

COOH

COOH

H2N

H2N

H
N

S
O

NaHCO3

S
O

N
COOH

CH3
O

2-

 : , , , .,
.
: , , , , ,
, ( , ).
: , , , , ,
, , ..
, - (, ).
: ,

-.

I -
Cefalexinum
Cefalexin
O

NH

C
CH

7 -

CH3
O

NH2

OH

Cephazolinum
Cefazolin
O

NH

C
CH2

N
N

Kefzol
Kefem

S
N

CH2
O

N
S

CH3

OH

[3-(5--1,3,4--2-)-7-(1--)-2-4]-
Cephalotinum natrium
Cefalotin sodic
O

C
CH2

NH
N

CH 2 - O - C - CH3

O
C

ONa

7-(2-)- a
9

II
Cefaclorum
Cefaclor
O

NH

C
CH

Cl
C

NH2

O
OH

(6R,7R)-7-[(R)--2-]-3--8--5--1-[4,2,0]-2--2-

III-
C

HN

N C

CH2 S

O
C

NH
H5C2 N

CH

HO

Cefoperazonum
Cefoperazon
N
S

N CH3

O
OH

Cefotaximum
Cefotaxim
O

N
H2N

NH

O
N

CH2 - O - C - CH3
C

N
OCH

OH
3

VI-
Cefpiromum
Cefpirom
O

N
H2N

NH

N
OCH

O
_

10

- -;
1;
;
80%- H2SO4 1%-
HNO3 ( );
.

: , .
:

;
;
;
:
+

NH2 H
N
O

NH3 H
N

S
+
CH3

HClO4

ClO4

CH3
COOH

COOH

OH

CH3 - CH
O

OH

SR
C

O
OH

SR

CH3 - CH
O

11
OH

(R=CH2CH2NH2);
(R=CH=CHNH2);
(R= CH2CH2NHC=NH).

Imipenemum
Imipenem
OH
4

CH3 - CH

6
7

3
2

S - (CH2)2 - NH - CH = NH
O
C
OH

N-

(5S,6R)-3-[[2-()]-6[ R]-1-]-7-1-[3,2,0]-2--2-

OH
CH3 - CH
O

6 5
1
7

3
2

NH

S - (CH2)2 - NH2
O
C
OH

+
H

HCl
OCH 3

OH

CH3 - CH
O

6 5
1
7

S - (CH2)2 - NH - CH = NH
O
C
OH

3
2

NH2

HOOC - CH - CH2 - S - (CH2)4

COOH
NH - C H
O

CH3
CH3

OH

N O

R - C - NH
N

HOOC - CH - (CH2)2 - O
R

OH

C - C - NH
O

12
CH
COOH

OH

Aztreonamum
Aztreonam

NH2
S

O
C - C - NH
N
O

CH3

COOH
CH3

CH3
H
N

SO3H

(Z)-2-[[[(2--4-)[[(2S,3S)-2--4--1--3-]]]]-]-2-

-
Sulbactamum natrium
Sulbactam de sodi
Sulbactam sodium

O
S

CH3
CH3
O
C
ONa

1,1-
:
;
.
.
.
. .
:
-;
.
13

Acidum clavulanicum
Acid clavulanic
H

CH - CH2 - OH
O
C
OH

:
.

OH

HO
HO

R 1 -NH

H, - C

NH - R1

6
1

NH
NH2

14
R

H, -OH

Streptomycini sulfas
Sulfat streptomicin
O
CHO

H3C

OH

O O
CH2OH

HO

OH

OH

HO

CH3NH

NH - C - NH2
NH

HN - C - NH2

OH

NH

Kanamycinum
Kanamycin

CH2OH
O

H2N-H2C

HO

. 3 H2SO4

NH2

HO

OH

H2SO4

OH
O
OH

NH2
NH2

O-3--3-- -D--(1 6)-[6--6--]- -D--(1 4)-2-- D

R -HN
1

R-HC

H3C
OH

H3C-NH
O

H2N

H2N-H2C

O
O

HO

Gentamycini sulfas
Sulfat de gentamicin

HO

HO
O

5 H2SO4

1: R= R1= 3
2: R= 3; R1=
1: R= R1=

CH2OH
OH
O

NH2

mikacini sulfas
2 Sulfat de amikacin

NH2

NH2

OH

. 2 H SO
2
4

OH
O
HO

OH
NH-C-CH-CH2-CH2-NH2
NH2

15

OH
HO
OH

c
(1,3--2,4,5,6)

HO
NH - C - NH2

H2N - C - NH

NH

NH

HO

O OH
CH2OH

O
H
C O

H3C

CH3NH

OH

OH

OH

OH

N--L-

L-

L-
4

H3C
5

O
H
C O
2

OH

O O
HO
CH2OH
CH3NH

OH

O
OH

HO
NH

H2O
NH - C - NH2

OH

NH

NaOH
NH - C - NH2

NH

OH

HO

C - NH2

OH

OH

OH

HO

HO

NH

2 NH3

OH

NaOH
HO
NH - C - NH2

NH
C - NH2
O

OH

CH3NH

NH

OH

O O
CH2OH

HO

NH

C - NH2

N--L-

NH

+
NH - C - NH2

NH

HO

NH

OH

H3C

HO

C - NH2

OH

OH

O
H
C O

2 NH3
2 CO2

HO
OH

HO
NH2

NH2

16

H3C

O
H
C O
OH

NaOH

Fe 3 +

OH

OH

CH3

OH

L-

Fe/3

O
CH3

L-.
:
O
:
Br

OH
H
N
C

NH

: Na[Fe(CN)5NO] + K3[Fe(CN)6] +
NaOH ( ) .

:
H
H
HO
OH
H
H2N - H2C

C
OH

HO

HCl
(conc.)

H
C

H2N - H2C

O
H

6--6-- D-

5-

CH3

CH3
H
OH

HO

+ H2N - H2C

O
H

HCl conc.

H
HO

OH

- H2O

17

H
C

CH3
HO

OH

HO

H
C

CH3

CH3

[O]
OH

FeCl3

OH

HO

CH3
HO

HCl conc.

CH2NH2

CH2NH2

: ( ), -, .

O
H2N - H2C

O
H

- H2O
H

5-
O

CH

CH2 - NH2

18

H3C
HO
H3C

OH OH
CH3
6
7

8
9

10

CH3

2
1

OH
12

11

13

CH2-CH3

H3C H3C OH

H3C

CH3
1
HO
3

OH

CH3

O
6

H3C

HO

OH

N CH
3

H3C 4

HO

OH

OH

OCH3

Aminoglicozide
OH

HO
HO

R 1 -NH

H, - C

NH - R1

NH
NH2
19

H, -OH

Streptomycini sulfas
Sulfat de streptomicin
O
H3C

CHO
OH

OH

OH

O O
HO
CH2OH

HO

NH - C - NH2

CH3NH

NH
HN - C - NH2

OH

NH

Kanamycinum
Kanamicin

CH2OH
O

H2N-H2C

HO

. 3 H2SO4

HO

NH2
OH

H2SO4

OH
O
OH

NH2
NH2

mikacini sulfas
Sufat de amikacin

20

CH2OH
O

H2N-H2C

HO

NH2

HO

OH

OH

2 H2SO4

O
HO

OH
NH-C-CH-CH2-CH2-NH2
NH2

Cu acizi minerali concentrai - hidroliza

O
H2N - H2C

- H2O
H

5-aminometilfurfurol

antronol

O
Ac

CH

CH2 - NH2

CH3
5

OH

OCH
Erythromycinum
3

CH3
3

5
4

CH3

Eritromicin

OH

H3C

N CH
H3C
3
H3C
6
HO

CH3
1
HO
3

H3C

10
11

H3C H3C

12

13

CH2-CH3
OH

21

Azithromycinum
Azitromicin
CH3
5

CH3
1
HO
3

H3C

8
9

10 11

H3C

1
2

N CH
H3C
3
H3C
HO 6

H3C

OH

OCH3
5

CH3
O
OH
12

H3C H3C

13

CH3

. H 2O

14

CH2-CH3
OH

22

23