Chapter 6 structures Flashcards
(27 cards)
Cephapirin
1st gen cephalosporin
3-acetoxy methyl cephalosporin
“Cephaloporanic acid (ester)”
chemically and metabolically unstable
Admin as Na+ injectable (no oral)
hydrolyzed to cyclized lactone (inactive)
short half life
low PPB
renally eliminated
use: MSSA and PSSP (similar to ASP), peptostreptococcus
Cephalothin
1st gen ceph
3-acetoxy methyl cephalosporin
“Cephaloporanic acid (ester)”
chemically and metabolically unstable
Admin as Na+ injectable (no oral)
hydrolyzed to cyclized lactone (inactive)
short half life
low PPB
renally eliminated
Use: MSSA and PSSP (similar to ASP), peptostreptococcus
Cefotaxime
3rd gen ceph
3-acetoxy methyl cephalosporin
Non-acidic AKI = resist NSBL, BSBL inactivation
“Cephaloporanic acid (ester)”
chemically and metabolically unstable
Admin as Na+ injectable (no oral)
hydrolyzed to cyclized lactone (inactive)
short half life = significant metabolism
low PPB
renally eliminated (TS + GF)
Use: PSSP, PRSP, MSSA, BLase producing H. influenza, M. catarrhalis, E. Coli, P. Mirabilis, other gram neg BSBL
Cefoxitin
2nd gen ceph
cephamycin (7-a-methoxy)
oral or IV
Use: G+, G -, B fragilis, E. coli, proteus, salmonella, G+ anaerobe, PSSP, MSSA
Good for dirty surgery prophylaxis
good for non-enterococci GUT infections (intra-ab abscess)
low PPB
Cefmetazole
2nd gen ceph
cephamycin (7-a-methoxy)
3-thioheterocycle
NMTT ring
IV
Use: G+, G -, B fragilis, E. coli, proteus, salmonella, G+ anaerobe, PSSP, MSSA
Good for dirty surgery prophylaxis
good for non-enterococci GUT infections (intra-ab abscess)
longer half life than cephalosporanic acid
more PPB, slow renal elim
cause desulfuram rxn and hypothrombonemia
Cefotetan
2nd gen ceph
cephamycin (7-a-methoxy)
3-thioheterocycle
NMTT ring
IV = chem unstable
chemically and metabolically stable so technically could give orally
Use: G+, G -, B fragilis, E. coli, proteus, salmonella, G+ anaerobe, PSSP, MSSA
Good for dirty surgery prophylaxis
good for non-enterococci GUT infections (intra-ab abscess)
longer half life, higher PPB, slow renal elim
cause desulfuram rxn and hypothrombonemia
Ceftazidime
3rd gen ceph
N-Acidic-alkoximino 3-QUAT
3’ group determines spectrum
acidic AKI group = resists NSBL, BSBL inactivation
Use: pseudo (non-AmpC) and some MRSA, BLase producing H. influenza, M. catarrhalis, E. coli, P. mirabilis, Non-ESBL non-AmpC producing enterobacteriaceae, neisseria
no affinity for strep
Quat: inc OM penetration for pseudo
have low MIC90
Free acid or Na+ IV, IM
Cefepime
4th gen ceph
N-acidic-alkoximino 3-QUAT
NON acidic AKI = resist NSBL, BSBL inactivation
has broadest spectrum, more active
use: staph, strep, PRSP, peptostreptococcus, BLase producing H influenza, M catarrahalis, E. Coli, P. mirabilis, Non-ESBL non-AmpC producing enterobacteriaceae, non-AmpC pseudo.
Ceftaroline
5th gen ceph
QUAT
Non acidic AKI = resist NSBL, BSBL inactivation
IV (prodrug available)
Use: PSSP, PRSP, MSSA, MRSA, MRSE, H. influenza, M. catarrhalis, E coli, P mirabilis, non-AmpC pseudo
Use in community acquired pneum.
PBP2a binds on quat
cleared renally
cefamandole naftate
2nd gen ceph
3-thioheterocycle and 7-polar fxn group (non ester form)
NMTT ring
ester prodrug = IV
hydrolyzes during reconstitution
No metabolism in body = metab stable
chemically unstable
longer half life (than cephalosporanic acid), more PPB, slow renal elim
use: PSSP, MSSA, H. influ, M catarrhalis, pasturella, eikenella, neisseria, E coli, P mirabilis
Resp. tract infection
cause desulfuram rxn and hypothrombonemia
cefuroxime axetil
note: without axetil, its not a prodrug
2nd gen ceph alkoximino
NON acidic AKI = resist NSBL, BSBL inactivation
oral prodrug = chem/metab stable
use: PSSP, PRSP, MSSA, H influ, M catarrhalis, G -, neisseria, E. coli BSBL, P. mirabilis
food increases absorption
low PPB
cefpodoxime proxetil
note: without axetil, its not a prodrug
marketed as 2nd gen ceph alkoximino, but is a 3rd gen b/c of AT ring
NON acidic AKI = resist NSBL, BSBL inactivation
oral prodrug = chem/metab stable
use: PSSP, PRSP, MSSA, H influ, M catarrhalis, G -, neisseria, E. coli BSBL, P. mirabilis
has AT (higher binding affinity for G - ) and AKI group
food increases absorption
AKI group = resist NSBL, BSBL
low PPB
cefditoren pivoxil
3rd gen ceph
N-methoxyimino
oral prodrug
hydrolysis –> active drug
food increases absorption
Use: PRSP, PSSP, H influ, M catarrhalis, E coli, P mirabilis, non-ESBL, non-AmpC producing enterobact
resp. tract infection
low PPB
Cefazolin
1st gen ceph
3-thioheterocycle
Na+ IV only = chem unstable
No metab = metab stable
orally inactive due to chem unstable 3-methylthioheterocycle group
Longer half life (than cephalosporanic acid), high PPB, slow renal elim
Use: MSSA, PSSP, peptostreptococcus
choice drug for clean surgery prophylaxis
Cefonicid
2nd gen ceph
3-thioheterocycle
7-polar fxn group
NO NMTT RING
DiNa+ IV = chem unstable
no metab = metab stable
longer half life (than cephalosporanic acid), more PPB, slow renal elim
use: PSSP, MSSA, H. influ, M catarrhalis, pasturella, eikenella, neisseria, E coli, P mirabilis
Resp. tract infection
Ceforanide
2nd gen ceph
7-polar fxn group
3-thioheterocycle
NO NMTT RING
free acid or Na+ IV = chem unstable
no metab = metab stable
longer half life (than cephalosporanic acid), more PPB, slow renal elim
use: PSSP, MSSA, H. influ, M catarrhalis, pasturella, eikenella, neisseria, E coli, P mirabilis
Resp. tract infection
Ceftrixaone
3rd gen ceph
3-thioheterocycle
N-methoxyimino
NON acidic AKI = resist NSBL, BSBL inactivation
Na+ and diNa+ IV = chem unstable
no metab = metab stable
longer half life, very high PPB, slow renal + biliary elim
use: PSSP, PRSP, BLase producing H influ, M catarr, E coli, P mirabilis, non-ESBL non-AmpC enterobact, neisseria (drug of choice)
ADR: biliary sludging, IM injection site pain
cefoperazone
3rd gen ceph
ureido
NMTT ring
Na+ IV = chem unstable
no metab = metab stable
use: MSSA and PSSP
long half life, high PPB
biliary excretion
ADR: Biliary sludging, desulfurame rxn with EtOH, hypothrombonemia in elderly/malnourished
Cefixime
3rd gen ceph
N-acidic-alkoximino
oral
COOH = better G - OM penetration
acid AKI group = resists NSBL, BSBL inactivation
no affinity for strep
use: H influ, M catarr, E coli, P mirabilis, enterobact, neisseria
low PPB
ceftibuten
3rd gen ceph
N-acidic-alkoximino
oral
COOH = better G - OM penetration
acid AKI group = resists NSBL, BSBL inactivation
no affinity for strep
use: H influ, M catarr, E coli, P mirabilis, enterobact, neisseria
low PPB
cephradine
1st gen ceph
7 polar fxn
chemically and metab unreactive
oral
low PPB
Use: PSSP, MSSA, H influ, M catarr, e coli, p mirabilis
cefadroxil
1st gen ceph
7 polar fxn group
chem and metab stable (unreactive) 3 substituent
oral
short half life, no metab, low PPB
renal elim (TS + GF)
Use: PSSP, MSSA, peptostreptococcus
Cephalexin
1st gen ceph
7 polar fxn group
chem and metab stable (unreactive) 3 substituent
oral
short half life, no metab, low PPB
renal elim (TS + GF)
Use: PSSP, MSSA, peptostreptococcus
loracarbef
2nd gen ceph
7 polar fxn group
Use: PSSP, MSSA, H influ, M catarr, E coli, P mirabilis
Oral
low PPB
