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CEPHALOSPORIN

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1

2

3

45678

N

SH H

N

COOH

O

H

C

OAc

O

CH2CH2CH2CH

H2N

COOH

nhanh ben 7-aminoadipic

Cephalosporin C

7-aminocephalosporinic acid (7-AC

1945: Cephalosporium acremonium

Peni N, cephalosporin P1,cephalosporin C

Cephalosoprin C :

- hot tnh KK khim tn, nhng hot tnh trn S. aureus.- bn vi peniciina!e c"a Bacillus subtillis

#ephao!porin $%

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azetidine-2-on

NH +

OHN

S

dihydrothiazine

NO

S

cephem

#ephao!porin & '(etidin-)-on * dih+drothia(incephem

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Cephalosporin C (hi!n

nhi!n"

CEPHALOSPORIN #$N

%&N' HP- / r0ng ph1 KK !ang gram m- 2ia t3ng kh4 n3ng kh5ng i betaactama!e- #4i thi6n v dc 80ng h9c

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N

O

67 CCe

ham

cin N

O

67

CCar

bace

he N

O

67

C

Oxace

h

)*N CH+%CEPHE

-h.n/ cephalosporin n0i ch.n/ 2n h3n penicillin i 67i aci8

oracarbe:

ce:o;itin atamo;e:

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Cephalosprin h= h> INH? 1: ce@aloin,NH? : ce@alori8in, ce@aBolin,NH? D: ce@alein, ce@a8roil, ce@aclor,

Cephalosprin h= h> IICe@a

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N

O

XHN R7

O

R

COOH

R31

37

H

)*N CH+% CEPHELi!n .an cJ. rKc Mc8n/

12

3

4567

8N

S

H HN

COOH

O

H

C

OAcO

CH2CH2CH2CH

H2N

COOH

nhanh ben 7-aminoadipic

Cephalosporin C

7-aminocephalosporinic acid (7-AC

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B5n t1ng hp tC cephao!porin #

IQCH

12

3

45678

N

SH H

N

COOH

O

H

C

OAc

O

CH2CH2CH2CH

H2N

COOH

nhanh ben 7-aminoadipic

Cephalosporin C

7-aminocephalosporinic acid (7-AC

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S

O

HNR1

O

H H

OAc

CO2SiMe3

protecting group

3

7

!C"#R1

C"

imino ch"ori$e

ROHR1

OR

imino ether

H2O

- R1CO2H

S

O

H2N H H

OAc

CO2H

3

7

7ACA

R2 C"

O

Aci$ ch"ori$e

S

O

HN

H H

OAc

CO2H

3

7

O

R2

Range o% cepha"o&porin&

%n/ hTp UACA 6 cMc chJ V3n/ Wn/cephalosporin

HNR1

7

''

O

H

!C"

C"

NR1

7

O

H

C"3!

C"

C"

''

''( (

R1

C"O

H

C"3!)O

Cch= Xo i

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%YNH CH+% Z% L[- B0t tinh thD trEng hoFc cG m?@ nhH, khIng mi.J?i cephao!porin cG mi @ h@nh ce:ae;in, ce:radin.

- #G n3ng !@Lt M@a+ c>c nhLt 8Nnh- $h1 OJP cL@ trQc cephem cho hai hLp th@P ))Rnm v?\]n IIce@a

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- #@ kh@An gram * P #epha SS x cephao!porin S.

- #@ kh@An gram +-,P cepha SS y cepha S, 8Fc bi6ttrn c@ kh@An kh5ng peniciin.

- _ot tnh tt 8i vi vi kh@An gram - 8ng r@0t8 kh5ng vi cepha S mEc ph4i ti b6nh vi6n(ce@a IIPh dhMn/ dh.n

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Cephalosporin h= h> hF III

z@Lt hi6n tC %ZVR, nhi@ tin b0 !o vi c5c th h6trcPnh hn 8i vi vi kh@An gram -, S# thLp.$hn phi tt / nhng vng cepha S v? SS khIng 8n

8c.` dng ch" +@ b{ng 8ng tim nhng c|ng cG m0t! phn t hot tnh khi dng @ng.

= > F

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Cephalosporin h= h> hF III

;S.l@ocephalosporinrLt bn 8i vi -

actama!e

SO

O

O

N

O CO2H

R3

ce%&u"o$in

#e:otiam

Qrei8o cephalosporin

#e:opera(on

A hF

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eho^i

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#e:ta(idim

Cephalosporin heM he htu IIIeho^i III

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#L@ trQc %-o;acephem kh5ng mnh trn gram - hi@ kh

Cephalosporin h= h> IIIOacepha

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_ot tnh mnh trn JK gram - ]rn ch"ng gram * v? hi@ kh t cG tha+ 81i. _ot tnh ch" +@ trn unterobacterie 8a 8 kh5ngP ce@oai

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Cephalosporin h= h>hF I

#e:pirom %ZZ#P c+copentenop+ridint3ng hot tnh kh5ng c@ kh@Angram * v? enterobacterie, JK titcephao!porina!e.

#e:epim %ZZ

# P -^-meth+p+rroidin.

N

SHN

H H

COOHO

R1-----------------------------------------------------------------------------

R2

O

NOR1

R2

N

SH2N

CH3 N

CH3 NH3C

Ce%pirom

Ce%epim

N

S

O

HN

N

O

H H

O

O

O

CH3

S

N

H2N N

1-+4R57R,-7-+26,-+2-Amino--thia*o"y",-+methoxyimino,acety"amino-2-carboxy-8-oxo-

#-thia-1-a*abicyc"o'2'9-oct-2-en-3-y"methy"-#545758-tetrahy$ro:uino"iniuminner &a"t

Ce./inome

CHv wNH CHQN'

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#ephao!porin th h6 % v? )P

- d> ph\ng phl@ th@jt nhLt ? nhng trng hp cGng@+ c nhim `taph+ococc@! !a@ m1.

- dng trong nhng trng hp nhim trng ngo?ib6nh vi6n