Chapter 5 Structures Flashcards
(18 cards)
Penicillin G
natural penicillin (NP)
true antibiotic
Use in strep BUT NOT IN staph
intermediate BL ring stability and higher solubility
BL instability limited absorption
admin: oral, IV or IM
half life: 0.5-1.5
median PPB
Pen V
natural penicillin (NP)
high oral bioavailability
use in strep BUT NOT IN staph
less reactive than Pen G due to electron withdrawing groups (-I) linked to the side chain carbonyl = slower hydrolysis
intermediate BL ring stability and higher solubility
BL instability limited absorption
admin: oral
half life: 0.5-1.5
median PPB
Methicillin
Antistaphylococcal penicillin
Aroyl ASP - designed to not be hydrolyzed by Group 2a Blases (staph)
created to combat NP resistance in bugs
IV only
not stable in gut
+R groups
use: MSSA, strep
More reactive than Pen G due to electron donating (+R) group linked to the side chain carbonyl = faster hydrolysis
Low BL ring stability
admin: injection
half life: 0.5-1.5
high PPB
Nafcillin
anthistaphylococcal penicillin
Aroyl ASP - designed to not be hydrolyzed by Group 2a Blases
IV and oral
not stable in gut
+R group
Use: endocarditis, MSSA, strep
More reactive than Pen G due to electron donating (+R) group linked to the side chain carbonyl = faster hydrolysis
Naf is completely conjugated
Low BL ring stability
admin: injection
high PPB = difficulty treating privileged compartment
undergoes significant hepatic metab.
high hepatic elimination
renal impairment does not increase half lives significantly
Isoxazole penicillin
Antistaphylococcal penicillin
designed to not be hydrolyzed by Group 2a Blases
oral and IV
stable in gut
group includes: oxacillin, cloxacillin, dicloxacillin, flucloxacillin
dicloxacillin and oxacillin are use in US
less reactive than Pen G due to electron withdrawing groups (-I) linked to the side chain carbonyl = slower hydrolysis
solubility - limited absorption
half life: 0.5-1.5
very high PPB
renal impairment does not increase half lives significantly
Mezlocillin
ureido-penicillin
extended spectrum penicillin
Use: G - , but NOT STREP
side chain stability-limited absorption
admin: injection
half life: 0.5-1.5
very low PPB
Amoxicillin
amino penicillin
less reactive than Pen G due to electron withdrawing groups (-I) linked to the side chain carbonyl = slower hydrolysis
solubility-limited absorption
admin: oral
half life: 0.5-1.5
low PPB
Ticarcillin
Carboxy-penicillin
Extended spectrum penicillin
Use: Gram - , strep
has an alpha carboxy acid
undergoes decarboxylation in the gut
Kills enterobact and pseudomonads because of CO2
COOH gives extended spectrum
side chain stability-limited absorption
admin: inj
half life: 0.5-1.5
median PPB
Azlocillin
Ureido-penicillin
extended spectrum penicillin
Use: Gram - , but NOT STREP
side chain stability - limited absorption
admin: injection
half life: 0.5-1.5
very low PPB
Carbenicillin
Carboxy-penicillin
Extended spectrum penicillin
Use: Gram - bugs, NOT STREP
too toxic for use
side chain stability-limited absorption
admin: inj
prodrug form allows oral bioavailability
half life: 0.5-1.5
median PPB
Ampicillin
Aminopenicillin
alpha amino gropu is EWG by induction (not in conjugation)
Hospital Use
less reactive than Pen G due to electron withdrawing groups (-I) linked to the side chain carbonyl = slower hydrolysis
solubility-limited absorption
admin: oral, IV
produg form enhances solubility and absorption
half life: 0.5-1.5
low PPB
Piperacillin
ureido-pen
extended spectrum pen
Used in the US
Use: Gram - , BUT NOT STREP
side chain stability-limited absorption
admin: inj
6-side chain instability
half life: 0.5-1.5
very low PPB
Sulbactam
BLI
use with ampicillin
IV
Clavulanic Acid
BLI - suicide inhibitor
use with amoxicillin or ticaricillin
oral and IV
Tazobactam
BLI - suicider inhibitor
use with piperacillin
IV
2 Oral drugs
Pen V
amoxicillin
2 IV drugs
ticarcillin
piperacillin
Oral and IV drugs
Pen g
Nafcillin
Isoxazole
Ampicillin
