PENICILINE DE SEMISINTEZĂ

Peniciline stabile în mediu acid

FENETICILINA

PHENETHYCILLINUM (DCI)

N

SCH3

CH3

COOH

NHC

O

CH

O

O

CH3

Acid (2S, 5R, 6R)-3,3-dimetil-7-oxo-6-(fenoxipropionamido)-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

((1-Fenoxietil)-penicilina sau (-fenoxietil)-penicilina)

• Sinonime: Penicilina B; Penicilina MV.

Feneticilina

N

SCH3

CH3

COOH

NHC

O

CH

O

O

CH3

Clorura aciduluialfa-fenoxipropionic

+NH(C2H5)3Cl

--

N(C2H5)3O CH C

O

ClCH3

+

6-APA

C

N CH

CS

C

C

CH3

CH3

COOHO

H2NH H

PF: BROXIL (SmithKline Beecham, Olanda) – capsule a 500 mg feneticilina potasica.

PROPICILINAPROPICILLINUM (DCI)

N

SCH3

CH3

COOH

NHC

O

CH

O

O

CH2

CH3

Acid (2S, 5R, 6R)-3,3-dimetil-7-oxo-6-(2-fenoxibutiramido)-4-tia-1-azabiciclo 3. 2. 0

heptan-2-carboxilic(1-Fenoxipropil-penicilina sau -Fenoxipropil-penicilina)

• Sinonim: Fenoxipropilpenicilina.

Propicilina

N

SCH3

CH3

COOH

NHC

O

CH

O

O

CH2

CH3

Clorura aciduluialfa-fenoxibutiric

+NH(C2H5)3Cl

--

N(C2H5)3O CH C

O

ClC2H5

+

6-APA

C

N CH

CS

C

C

CH3

CH3

COOHO

H2NH H

• PF: BAYCILLIN MEGA (Bayer Vital, Germania) – comprimate filmate a 1 mil. UI / cp.

FENBENICILINAPHENBENICILLINUM (DCI)

N

SCH3

CH3

COOH

NHC

O

CH

O

O

Acid (2S, 5R, 6R)-3,3-dimetil-7-oxo-6-(2-fenoxi-2-fenilacetamido)-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

(-fenoxibenzilpenicilina)

Fenbenicilina

N

SCH3

CH3

COOH

NHC

O

CH

O

O

Clorura aciduluialfa-fenoxifenilacetic

+NH(C2H5)3Cl--

N(C2H5)3O CH C

O

ClC6H5

+

6-APA

C

N CH

CS

C

C

CH3

CH3

COOHO

H2NH H

AZIDOCILINAAZIDOCILLINUM (DCI)

N

S

COOH

CH3

CH3

O

NHC

O

N3

Acid (2S, 5R, 6R)-6-(R)-2-azido-2-fenilacetamido- 3,3-dimetil-7-oxo 4-tia-1-azabiciclo

3. 2. 0 heptan-2-carboxilic

• PF: LONGATREN (Bayer, Austria) – comprimate a 750 mg azidocilin\ / cp.

CLOMETOCILINACLOMETOCILLINUM (DCI)

N

SCH3

CH3

COOH

NHC

O

CH

OOCH3

Cl

ClAcid (2S, 5R, 6R)-3,3-dimetil-7-oxo-6-2-(3, 4-diclorofenil)-2-metoxi-acetamido-4-

tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic(3,4-diclor--metoxibenzilpenicilina)

• Sinonim: Penicilina 356.

• PF: RIXAPEN (Menarini, Belgia) – comprimate a 500 mg

Peniciline rezistente la penicilinaza stafilococică

Peniciline rezistente la penicilinază şi instabile la aciditatea gastrică

METICILINA SODIC|METHICILLINUM NATRICUM (DCI)

N

SCH3

CH3

COO-

NHC

O

O

OCH3

OCH3

Na+ . H2O

Sarea de sodiu a acidului (2S, 5R, 6R)-6-(2,6-dimetoxibenzamido)- 3,3-dimetil-7-oxo 4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

• Sinonim: Dimetoxifenecilina.

Clorura acidului2,6-dimetoxibenzoic

+NH(C2H5)3Cl

--

N(C2H5)3

OCH3

OCH3

+

6-APA

C

N CH

CS

C

C

CH3

CH3

COOHO

H2NH H

CO

Cl

N

SCH3

CH3

COOH

NHC

O

O

OCH3

OCH3

Meticilina

• PF: STAFICYN (Firma, Italia) – flacoane cu pulbere injectabilă (1 g meticilină sodică)

Peniciline cu structură izoxazolică

Peniciline rezistente la penicilinază şi stabile la aciditatea gastrică

OXACILINA SODIC|OXACILLINUM NATRICUM (DCI, FR X)

N

SCH3

CH3

COO-

NHC

O

ON

O CH3

Na+ . H2O

Sarea de sodiu a acidului (2S, 5R, 6R)-3,3-dimetil-6-(5-metil-3-fenil-4-izoxazolcarboxamido)-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

• Sinonim: Oxazocilina.

Clorura acidului3-fenil-5-metil-izoxazolil-4-carboxilic

+NH(C2H5)3Cl

--

N(C2H5)3+

6-APA

C

N CH

CS

C

C

CH3

CH3

COOHO

H2NH H

N

SCH3

CH3

COOH

NHC

O

ON

O CH3

NO CH3

Cl

OC

Oxacilina

• PF: OXACILINA (Antibiotice S.A.; Europharm; Lek Pharmatech, România) – capsule 250 mg

oxacilina sodica / cps; pulbere pentru solutie injectabila (250 mg, 500 mg sau 1 g oxacilina sodica).

BACTOCILL (SmithKline Beecham, SUA) - pulbere pentru solutie injectabila - 1 g şi 2 g

oxacilina sodica.

STAPENOR (Bayer, Austria) - pulbere pentru solutie injectabila - 1 g oxacilina sodica.

CLOXACILINA SODIC|CLOXACILLINUM NATRICUM (DCI)

N

SCH3

CH3

COOH

NHC

O

ON

O CH3Cl

Na+ . H2O

Sarea de sodiu a acidului (2S, 5R, 6R)-6-3-(o-clorofenil)-5-metil-4-izoxazolcarboxamido)- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-

carboxilic

Clorura acidului3-o-clorofenil-5-metil-izoxazolil-4-carboxilic

+NH(C2H5)3Cl

--

N(C2H5)3

Cl

+

6-APA

C

N CH

CS

C

C

CH3

CH3

COOHO

H2NH H

N

SCH3

CH3

COOH

NHC

O

ON

O CH3Cl

NO CH3

Cl

OC

Cloxacilina

Na+ . H2O

• PF. ORBENIN (SmithKline Beecham, Australia; Singapore; Africa de Sud;

Irlanda) – capsule 250 [i 500 mg ; sirop 125 mg / 5 ml; pulbere pentru solu]ie

injectabil\ (250 mg [i 500 mg);

AMPICLOX (Europharm SA, România) – capsule con]inând cloxacilin\

sodic\ (echivalentul a 250 mg cloxacilin\) [i ampicilin\ trihidrat (echivalentul a

250 mg ampicilin\ anhidr\).

DICLOXACILINA SODIC|DICLOXACILLINUM NATRICUM (DCI)

N

SCH3

CH3

COOH

NHC

O

ON

O CH3Cl

Cl

Na+ . H2O

Sarea de sodiu a acidului (2S, 5R, 6R)-6-3-(2,6-diclorofenil)-5-metil-4-izoxazolcarboxamido)- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0

heptan-2-carboxilic

• PF: DICLOCIL (Bristol-Myers Squibb) - capsule 250 şi 500 mg ; pulbere pentru solutie injectabila (500 mg şi 1000 mg);

DYNAPEN (Apothecon, SUA) - capsule 250 şi 500 mg.

FLUCLOXACILINA SODIC|FLUCLOXACILLINUM NATRICUM (DCI)

N

SCH3

CH3

COOH

NHC

O

ON

O CH3Cl

F

Sarea de sodiu a acidului (2S, 5R, 6R)-6-3-(2-cloro-6-fluorofenil)-5-metil-4-izoxazolcarboxamido)- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-

carboxilic

• Sinonim: Floxacilin\.

• PF. FLOXAPEN (GlaxoSmithKline) - capsule 250 si 500 mg ; sirop (125 mg / 5 ml); pulbere pentru solutie injectabila (250 mg, 500 mg si 1000 mg).

Alte peniciline rezistente la penicilinază şi stabile la aciditatea gastrică

NAFCILINA SODIC|NAFCILLINUM NATRICUM (DCI)

N

SCH3

CH3

COO-

NHC

O

O

OC2H5

. H2ONa+

Sarea de sodiu a acidului (2S, 5R, 6R)-6-(2-etoxi-1-naftamido)- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

PF: UNIPEN (Wyeth Ayerst, SUA) – capsule 250 si 500 mg ; pulbere pentru solutie injectabila (1000 mg si 2000 mg).

Peniciline cu spectru de activitate lărgit

Aminopeniciline

AMPICILINA SODIC| AMPICILLINUM NATRICUM (DCI, FR X)

Na+

N

SCH3

CH3

COO-

NHC

O

CH

ONH2

(2S, 5R, 6R)-6-(R)-2-amino-2-fenilacetamido- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilat de sodiu

• Sinonim: Aminobenzilpenicilina.

Clorura acidului alfa-amino-fenil acetic

CH

NH2

+

6-APA trimetil- silil ester

C

N CH

CS

C

C

CH3

CH3

COOO

H2N

Si

CH3

CH3

CH3

H H

N

SCH3

CH3

COOH

NHC

O

CH

ONH2

Cl

OC

. HCl

dimetilanilinaapa

pH = 5

. 3 H2O

6-APA sare cu trietilamina

C

N CH

CS

C

C

CH3

CH3

COO-

O

H2NH H

N

SCH3

CH3

COOH

NHC

O

CH

ONH2

CH COOK

NH2

alfa-amino-fenilacetat de potasiu

+ CH3 C CH2

O

COOC2H5

acetil acetat de etil

-H2OCH COOK

N CCH3

CH2COOC2H5

Baza Schiff

CH COOK

NH

CH3C CH C

O

OC2H5

forma enaminica

(CH3)3C COClclorura acidului pivalic

- KClCH

NH

CH3C CH C

O

OC2H5

COO

C O

C(CH3)3

agent de acilare (anhidrida mixta)

NH(C2H5)3+

- (CH3)3C COOH

acid pivalicN

SCH3

CH3

COO-

NHC

O

CH

ON

C CH2COOC2H5H3C

NH(C2H5)3+

H2O (HCl)

- CO2

- C2H5OH

- CH3COCH3- (C2H5)3N . HCl Ampicilina

• PF. AMPICILINA (Antibiotice SA; Europharm SA; Lek Pharmatech; Ropharma, România) -

capsule cu 250 mg si 500 mg ampicilina anhidra, pulbere pentru suspensie orala (125 mg si 250

mg / 5 ml), flacoane cu 250 mg, 500 mg si 1000 mg pulbere uscata sterila ampicilina sodica pentru

administrare parenterala;

PAMECIL (Medochemie, Cipru) – pulbere pentru solutie injectabila (500 mg si 1000 mg)

STANDACILLIN (Biochemie, Austria) - capsule cu 250 mg si 500 mg ampicilina trihidrat;

granule pentru suspensie orala (125 mg si 250 mg / 5 ml), pulbere pentru solutie injectabila (500

mg, 1000 mg si 2000 mg).

Derivaţi biologic reversibili ai ampicilinei (proampiciline)

PIVAMPICILINA CLORHIDRATPIVAMPICILLINUM HYDROCHLORIDUM (DCI)

N

SCH3

CH3

COOCH2

NHC

O

CH

ONH2 OCO C(CH3)3

. HCl

(2S, 5R, 6R)-6-(R)-2-amino-2-fenilacetamido- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilat de pivaloil-oxi-metil

N

SCH3

CH3

COOCH2

NHC

O

CH

ONH2 OCO C(CH3)3

N

SCH3

CH3

COOH

NHC

O

CH

ONH2

+ CH2O + HOOC C(CH3)3

- H2O

PF: PONDOCILLIN (Leo Pharma, Danemarca; Norvegia; Suedia) – comprimate 500 mg; suspensie 35 mg /ml.

TALAMPICILINA CLORHIDRATTALAMPICILLINUM HYDROCHLORIDUM (DCI)

N

SCH3

CH3

COO

NHC

O

CH

ONH2

O

O

. HCl

(2S, 5R, 6R)-6-(R)-2-amino-2-fenilacetamido- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilat de 3-oxo-1,3-dihidroizobenzofuran-1-il

• Sinonim: Ampicilin-ftalidil clorhidrat

BACAMPICILINA CLORHIDRATBACAMPICILLINUM HYDROCHLORIDUM (DCI)

N

SCH3

CH3

COO

NHC

O

CH

ONH2 CH

CH3

O COOC2H5

. HCl

(2S, 5R, 6R)-6-(R)-2-amino-2-fenilacetamido- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilat de 1-(etoxi-carbonil-oxi)-etil

• PF: PENGLOBE (Astra Zeneca, UK-Suedia) – comprimate 200 mg.

HETACILINAHETACILLINUM (DCI)

N

SCH3

CH3

COOHO

N N

O

H3C CH3

H

Acid (2S, 5R, 6R)-6-(R)-2,2-dimetil-5-oxo-4-fenil-1-imidazolinil- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

• Sinonime: Etacilina; Fenazacilina.

N

SCH3

CH3

COOHO

N

SCH3

CH3

COOH

NHC

O

CH

ONH2

+ H3C C CH3

O

N N

O

H3C CH3

H

- H2O

METAMPICILINAMETAMPICILLINUM (DCI)

N

SCH3

CH3

COOH

NHC

O

CH

ON CH2

Acid (2S, 5R, 6R)-6-(R)-2-(metilen-amino)-2-fenilacetamido- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo

3. 2. 0 heptan-2-carboxilic

• PF: DOMPIL (Spyfarma, Spania) – capsule a 250 mg si 500 mg.

Derivaţi biologic ireversibili ai ampicilinei

AMOXICILINA TRIHIDRATAMOXICILLINUM TRIHYDRICUM (DCI, FR X)

N

SCH3

CH3

COOH

NHC

O

CH

ONH2

HO . 3 H2O

Acid (2S, 5R, 6R)-6-(R)-(-)-2-amino-2-(p-hidroxi-fenil)-acetamido- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

• Sinonim: p-Hidroxiampicilin\.

CH

NH

CH3C CH C

O

OC2H5

COO

C OOC2H5

HOCH COONa

NH

CH3C CH C

O

OC2H5

HO

CH COONa+

NH2

HO

H2O

CO2-

N

SCH3

CH3

COOH

NHC

O

CH

ONH2

HO

CH3COCH3-

C2H5COOH-

N

SCH3

CH3

COOH

NHC

O

CH

ONH

HO

H3C C

CH C

OC2H5

O

C2H5 OH-

agent de acilare (anhidrida mixta)

NaCl-

C2H5O COCl

H2O-

acetil acetat de etil

CH3 C CH2

O

COOC2H5

fenil acetat de sodiualfa-amino-p-hidroxi

HH

C

C

CH

SC

N

CCH3

CH3

COOHO

H2N

6-APA

sare Dane

amoxicilina

• PF: AMOXICILINA (Antibiotice SA; Lek Pharmatech; Europharm; Arena Group, România /

Ozone Laboratories Ltd, UK) – capsule 250 mg si 500 mg; pulbere pentru suspensie orala (125

mg / 5 ml; 250 mg / 5 ml);

OSPAMOX (Sandoz GmbH, Austria) – comprimate filmate 500 mg si 1000 mg; capsule 250

mg; pulbere pentru suspensie orala (125 mg / 5 ml; 250 mg / 5 ml);

DISPAMOX (Lek Pharmatech, România) – comprimate dispersabile 1000 mg;

RANOXIL (Ranbaxy Laboratories Ltd, India) - pulbere pentru suspensie orala (125 mg / 5 ml;

250 mg / 5 ml).

AMOXIL (SmithKline Beecham, UK) - fiole a 250 mg, 500 mg sau 1 g amoxicilina sub forma

de sare de sodiu; capsule a 250 mg sau 500 mg; pulbere pentru preparare de sirop (125 sau 250

mg / 5 ml); pulbere pentru suspensie orala de uz pediatric (125 mg / 1,25 ml).

EPICILINAEPICILLINUM (DCI)

N

SCH3

CH3

COOH

NHC

O

CH

ONH2

Acid (2S, 5R, 6R)-6-(R)-2-amino-2-(1,4-ciclohexadien-1-il)-acetamido- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

• Sinonim: Dihidroampicilina.

CH

NH2

COOHLi / NH3

NaOCH3

CH

NH2

COONa

acid alfa-aminofenil acetic

1,4-ciclohexadienil-alfa-amino-acetat de sodiu

CH3 C CH2

O

COOCH3

acetilacetat de metil

- H2O

CH

NH

COONa

CH3C CH C

O

OCH3

sare Dane

C2H5O COCl

- NaClCH

NH

COO

CH3C CH C

O

OCH3

C

O

OC2H5

anhidrida mixta

N

S

COOH

CH3

CH3

O

H2N

6-APA

C2H5OH

CO2

-

-

N

S

COOH

CH3

CH3

O

NHCH

NH

C

CH3C CH C

O

OCH3

O

CH3COOH

CH3COCH3

-

-

H2O

N

S

COOH

CH3

CH3

O

NHCH

NH2

C

O

epicilina

CICLACILINACYCLACILLINUM (DCI)

N

SCH3

CH3

COOH

NHC

O

ONH2

Acid (2S, 5R, 6R)-6-(1-aminociclohexancarboxamido)- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

• PF. CILINASE (Dovalle, Brazilia) – comprimate a 500 mg.

Amidinopeniciline

AMDINOCILINA

AMDINOCILLINUM (DCI)

N

SCH3

CH3

COOH

NCH

O

N

Acid (2S, 5R, 6R)-6-(hexahidro-1H-azepin-1-il)-metilenamino- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

• Sinonime: Mecilinam; Amidinopenicilina HX; Penicilina Hx.

• PF. COACTIN (Roche, Elvetia) – pulbere pentru solutie injectabila (250 mg, 500 mg şi 1000 mg).

AMDINOCILIN PIVOXIL

AMDINOCILLINUM PIVOXYLUM (DCI)

N

SCH3

CH3

COOCH2

NCH

OO C C(CH3)3

ON

(2S, 5R, 6R)-6-(hexahidro-1H-azepin-1-il)-metilenamino- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilat de 2,2-(dimetil-1-oxopropoxi) metil

• Sinonime: Pivmecilina; Pivamdinocilina.

N

SCH3

CH3

COOCH2

NCH

OO C C(CH3)3

ON

N

N

SCH3

CH3

COOH

NCH

O

+ CH2O + HOOC C(CH3)3- H2O

-Carboxipeniciline

CARBENICILINA

CARBENICILLINUM (DCI)N

S CH3

CH3

COOH

NHC

O

CH

OCOOH

Acid (2S, 5R, 6R)-6-(-carboxi-fenilacetamido)- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-

carboxilic

CH COOH

COOH

2 PCl5

- 2 HCl-2 POCl3

CH COCl

COCl

C C

COCl

O

cetena

N

SCH3

CH3

COOH

H2N

O

+

N

SCH3

CH3

COOH

NHC

O

CH

OCOCl

HOH

- HClN

SCH3

CH3

COOH

NHC

O

CH

OCOOH

• PF. CARBENICILINA (Antibiotice SA, România) - flacoane cu pulbere uscata sterila, sare de sodiu, echivalent cu 1 g sau 5 g carbenicilina.

INDANIL CARBENICILINA

INDANYL CARBENICILLINUM (DCI)

COO

O

CH

O

C NH

COOH

CH3

CH3S

N

Acid (2S, 5R, 6R)-6--(5-indaniloxi) carbonil-fenilacetamido- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

• Sinonim: Carindacilina.

• PF. GEOCILLIN (Pfizer, USA) – comprimate

FENIL CARBENICILINA

PHENYL CARBENICILLINUM (DCI)

CH3

CH3

NO

NH

O

CH

COO

C

COOH

S

Acid (2S, 5R, 6R)-6--(fenoxicarbonil)-fenilacetamido- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

• Sinonim: Carfecilina.

TICARCILINA

TICARCILLINUM (DCI)

N

S

COOH

CH3

CH3NHC

O

O

CH

COOH

S

Acid (2S, 5R, 6R)-6-(-carboxi-3-tienilacetamido)- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

N

S

COOH

CH3

CH3NHC

O

O

CH

COOH

S

S

CH

COOH

COClSOCl2

S

CH

COOH

COOH

N

S

COOH

CH3

CH3H2N

O+

- HCl

• PF. TICAR (SmithKline Beecham, USA) – pulbere sterila injectabila (1 g si 5 g ticarcilina);

TICARPEN (SmithKline Beecham, Fran]a; Olanda; Spania)

TEMOCILINA

TEMOCILLINUM (DCI)

N

SCH3

CH3

COOH

NHC

O

CH

OCOOH

OCH3S

Acid (2S, 5R, 6R)-6-(carboxi-3-tienilacetil) amino-6-metoxi- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

• PF: NEGABAN (Eumedica, Elvetia) - pulbere sterila injectabila (1 g temocilina sodica).

Ureidopeniciline

PIPERACILINA

PIPERACILLINUM (DCI)

N

OC

NHO

CH

O

C NH

COOH

CH3

CH3S

N

N

C2H5

O

O

Acid (2S, 5R, 6R)-6-(R)-2-(4-etil-2,3-dioxo-1-piperazin-carboxamido)-2-fenilacetamido- 3,3-dimetil-7-oxo-4-tia-1-

azabiciclo 3. 2. 0 heptan-2-carboxilic

N

S

COOH

CH3

CH3NHC

O

O

CH

NH

NH2

CH COOH + NN

O O

H5C2 COCl(C2H5)3N

(C2H5)3NH Cl-+

-

N

N O

O

C

C2H5

O

NH

CH COOH

N

S

COO-

CH3

CH3H2N

O(C2H5)3NH

++

ClCOOC2H5

C O

N

N O

O

C2H5

acid -(4-etil-2,3-dioxo-1-piperazino-

carbonilamino)-fenilacetic

-fenilglicina clorura de 4-etil-2,3-dioxo-1-piperazino-carbonil

• PF: PIPRIL (Wyeth, Austria; Irlanda) - pulbere sterila injectabila (1 g sau 2 g piperacilina sodica);

PIPRACIL (Lederle, USA)

AZLOCILINA

AZLOCILLINUM (DCI)

N

SCH3

CH3

COOH

NHC

O

CH

ONH

C O

N

N

O

H

Acid (2S, 5R, 6R)-6-(R)-2-(2-oxo-1-imidazolidin-

carboxamido)-2-fenilacetamido- 3,3-dimetil-7-oxo-

4-tia-1-azabiciclo 3. 2. 0 heptan-2-carboxilic

N

S

COOH

CH3

CH3NHC

O

O

CH

NH2

N N

O

C

O

Cl H+

(C2H5)3N

(C2H5)3NH Cl-+

-

N

S

COOH

CH3

CH3NHC

O

O

CH

NH

N

N

O

C O

H

ampicilinaN-cloro-carbonil-imidazolidin-

2-ona

• PF: SECUROPEN (Bayer, Germania; Austria; Irlanda) – pulbere sterila pentru solutie injectabila (2g si 5 g azlocilina).

MEZLOCILINA

MEZLOCILLINUM (DCI)

N

SCH3

CH3

COOH

NHC

O

CH

ONH

C O

N

N

O

SO2 CH3

Acid (2S, 5R, 6R)-6-(R)-2-3-(metil-sulfonil)-2-oxo-1-imidazolidin-carboxamido-

2-fenilacetamido- 3,3-dimetil-7-oxo-4-tia-1-azabiciclo 3. 2. 0 heptan-2-

carboxilic

• PF. BAYPEN (Bayer, Germania; Austria; Fran]a; Italia; Spania; Israel) - pulbere sterila pentru

solutie injectabila (echivalentul a 1g si 2 g mezlocilina).