chapter 8 Flashcards
accidentally discovered the
antibacterial properties of
penicillin from Penicillium
notatum in 1929
Sir Alexander Fleming
purify penicillin and introduced it into
therapy
Florey & Chain
discovered the anthrax bacilli
Pasteur & Joubert
a substance produced by
microorganisms, which has the
capacity of inhibiting the growth
and even of destroying other
microorganisms (Waksman,
1942)
ANTIBIOTIC
β-LACTAM
ANTIBIOTICS
*Penicillins
* Cephalosporins
interfere with the last step of
bacterial cell wall synthesis
(transpeptidation or cross linking of peptidoglycan
chains)
β-LACTAM
ANTIBIOTICS
beta-lactam attached to
thiazolidine ring
- nucleus: 6-aminopenicillanic
acid
PENICILLINS
enzymes that catalyze the
hydrolytic opening of the β-lactam
ring of penicillins to produce
inactive penicilloic acid (S.
aureus and most gram-negative
bacteria)
Penicillinases (β-lactamases)
Benzylpenicillin
* given IV/IM
* was made available in the form of
water-soluble salt of potassium,
sodium and calcium
* poorly absorbed from the intestinal
tract, oral doses must be very large
PENICILLIN G
- its rapid elimination from the
bloodstream led to the
development of repository forms - Repository Forms (IM): Pen G
Benzathine, Pen G Procaine - DOC for many bacterial infections
(Ex: Rheumatic Heart Disease in
children and Syphilis)
PENICILLIN G
Crysticillin®, Duracillin®,
Wycillin®
* mixture of penicillin with
procaine HCl
Penicillin G Procaine
Bicillin®, Permapen®
* gives the compound great
stability and prolonged
duration of action
Penicillin G Benzathine
Phenoxymethylpenicillin
* Pen Vee®, V-Cillin®
* acid stable thus used orally
Penicillin V
2,6-dimethoxyphenylpenicillin
* Staphcillin®
- off the market due to high incidence of
interstitial nephritis - absence of the benzyl methylene group of penicillin G and the steric protection by the 2- and 6-methoxy groups makes it resistant to penicillinase
METHICILLIN
6-(2-ethoxy-1-naphthyl)penicillin sodium
* Unipen®
- acid stable enough to be used orally
- relatively small amounts are excreted
through kidneys, with the major portion
excreted in the bile - can be given to patients with renal
problem
NAFCILLIN
Isoxazoyl Penicillins:
*Oxacillin
* Cloxacillin
* Dicloxacillin
Prostaphlin®
*resistant to acid
hydrolysis thus
administered orally
OXACILLIN
Tegopen®
* resembles oxacillin but oral
absorption is more
enhanced
CLOXACILLIN
Dynapen®, Pathocil®,
Veracillin®
* similar to cloxacillin
* enhanced stability
DICLOXACILLIN
have an antibacterial spectrum similar
to that of Pen G but are more
effective against gram-negative bacilli
AMINOPENICILLINS
Penbritn®, Polycillin®,
Omnipen®, Amcill®, Principen®
* poor GI absorption
* more frequently administered
parenterally
* not resistant to penicillinase
AMPICILLIN
used in UTI caused by E.coli or
P.mirabilis
* DOC for Haemophilus influenzae
infection
oral dose should be repeated every
6 hours because its is excreted
rapidly and unchanged through the
kidneys
AMPICILLIN
DOC for gonorrhea
Ampicillin + Probenecid
Prodrugs of Ampicillin
-Bacampicillin
* Cyclacillin
* Hetacillin