Unit 1

Question 1

penicillin G

Answer 1

Natural penicillin.
Very active against sensitive bacteria.
Gram + only.
Very acid labile.
Readily hydrolyzed by B-lactamases.

Question 2

penicillin V

Answer 2

Natural penicillin.
Very active against sensitive bacteria.
Gram + only.
Less acid labile than penicillin V because of modification.
Readily hydrolyzed by B-lactamases.

Question 3

methicillin

Answer 3

B-lactamase Resistant Penicillin.
Less potent but more resistant.
Very acid labile.
Even more acid labile than penicillin G - side chain electron rich.

Question 4

Nafcillin

Answer 4

B-lactamase Resistant Penicillin.
Most active of class.
Orally active.

Question 5

Isoxazoyl Penicillins

Answer 5

B-lactamase Resistant Penicillins.
Oxacillin - H, H.
Cloxacillin - Cl, H.
Dicloxacillin - Cl, Cl.
Each are orally active.
Very good resistance.

Question 6

Ampicillin

Answer 6

Aminopenicillin.
NH2 extends spectrum to Gram -.
NH2 in R-form.
Prodrug form Bacampicillin for GI absorption (Diarrhea, microbiome damage).
Vulnerable to B-lactamase.

Question 7

Amoxicillin

Answer 7

Aminopenicillin.
NH2 extends spectrum to Gram -.
Para-hydroxyampicilin
NH2 in R-form.
2x as potent as ampicillin.
Combine with clavulanic acid.

Question 8

Carbenicillin

Answer 8

Extended Spectrum Penicillin.
A-Carboxypenicillin subclass.
Most active type of penicillin towards Gram-, including Ps. aeruginosa.
Decarb in acid to form PenG.
B-lactamase sensitive.
Acid labile - prodrugs available.

Question 9

Ticarcillin

Answer 9

Extended Spectrum Penicillin.
A-Carboxypenicillin subclass.
Most active type of penicillin towards Gram-, including Ps. aeruginosa.
Thiphene analog of carbenicillin: 2-4x as potent vs. Ps. aeruginosa.
W/ B-lactamase Inhib or aminoglycoside to extend spectrum.

Question 10

Pipericillin

Answer 10

Extended Spectrum Penicillin.
A-Acylureidopenicillin Subclass.
Ampicillin derivative.
Most active type of penicillin towards Gram-, including Ps. aeruginosa.
2,3-diketopiperazine substituent.
Retains good Gram+ activity.
B-lactamase sensitive - bulk not close enough to carbonyl sidechain.

Question 11

Azlocillin/Mezlocillin

Answer 11

Extended Spectrum Penicillin.
A-Acylureidopenicillin Subclass.
Ampicillin derivative.
Most active type of penicillin towards Gram-, including Ps. aeruginosa.
Both more potent than carbenicillin towards Ps. aeruginosa.
Acid labile.
B-lactamase sensitive.

Question 12

Cephalothin

Answer 12

Cephalosporin.
First Generation.
Good Gram+, Modest Gram-.
Not orally active
Good B-lactamase resistance; most resistant of First Gen.

Question 13

Cefazolin

Answer 13

Cephalosporin.
First Generation.
Good Gram+, Modest Gram-.
Parenteral.
Longest t1/2 of First. Gen.
Good B-lactamase resistance.

Question 14

Cephalexin

Answer 14

Cephalosporin.
First Generation.
Good Gram+, Modest Gram-.
Side-chain like Ampicillin.
Orally active - Methyl at C-3.
Good B-lactamase resistance.

Question 15

Cefproxil

Answer 15

Cephalosporin.
Second Generation.
Good Gram+, Decent Gram-.
Side-chain like Amoxicillin.
Orally active.
Good B-lactamase resistance.

Question 16

Cefuroxime

Answer 16

Cephalosporin.
Second Generation.
Good Gram+, Decent Gram-.
Oxime ether - syn config.
Anti-config: poor B-lactamase resistance.
CSF penetration - Meningitis.
Axetil prodrug - absorption.
Good B-lactamase resistance.

Question 17

Cefoxitin

Answer 17

Cephamycin

?

Question 18

Cefotaxime

Answer 18

Cephalosporin.
Third Generation.
Decent Gram+, Good Gram-.
Syn-oxime ether - potent and very B-lactamase resistant.
Aminothiazole - increased activity, especially in Enterobacteria.
Good B-lactamase resistance.

Question 19

Ceftriaxone

Answer 19

Cephalosporin.
Third Generation.
Decent Gram+, Good Gram-.
Most widely used injectable cephalosporin.
Good B-lactamase resistance.

Question 20

Cefepime

Answer 20

Cephalosporin.
Fourth Generation.
Good Gram+, Good Gram-.
Parenteral.
Quarternary amine - good leaving group; results in charge; good for gram-.
100% excreted in urine - UTIs.
Can cross BBB - Meningitis.

Question 21

Ceftaroline fosamil

Answer 21

Cephalosporin.
Fifth Generation.
Prodrug.
Good Gram+, Gram- good but less than 4th Gen, especially with Ps. aeruginosa.
Active against MRSA.
CAPB and acute bacterial skin infections
Parenteral.
Fosamil is the P containing group on the right.

Question 22

Aztreonam

Answer 22

Monobactam.
Weak antibacterial activity but highly resistant to B-lactamase.
Many Gram-, but no Gram+.
Parenteral.
Aztreonam lysine - lyophilized for inhalation for Ps. aeruginosa in CF patients.

Question 23

Clavulanic Acid

Answer 23

B-lactamase Inhibitor.
Class One.
Oxapenam.
Weak broad antibacterial.
Inhibits many B-lactamases.
Synergistic with many B-lactams.
w/ Amoxicillin = Augmentin.
w/ Ticarcillin = Timentin.

Question 24

Sulbactam

Answer 24

B-lactamase Inhibitor.
Class One.
Weak antibiotic activity.
Potentiates activity of ampicillin and carbenicillin.

Question 25

Tazobactam

Answer 25

B-lactamase Inhibitor. Class One. Broad B-lactamase inhibition. Goes with Pipericillin.

Question 26

Thienamycin

Answer 26

B-lactamase Inhibitor. Class Two. A Carbapenem - double bond increases reactivity. Developed as an antibiotic but used as an inhibitor now. Good antibacterial activity however. Unstable in concentrated solution - polymerizes. Easily inactivated by DHP-1.

Question 27

Imipenem

Answer 27

Carbapenem Antibiotic. Formimide derivative of Thienamycin. True antibiotic. Stable against Serine B-lactamases and inhibits many Gram- B-lactamases. Co-Admin. with Cilastatin; inhibits DHP-1. Seizure in 2%

Question 28

Meropenem

Answer 28

``` Carbapenem Antibiotic. Newer than Imipenem. Extremely broad spectrum. Better in-vivo for Ps. Aer than Imipenem. Stable against Serine B-lactamases. No Cilastatin required. Only slow hydrolysis by DHP-1. Good CSF penetration. Fewer seizures. ```

Question 29

Ertapenem

Answer 29

``` Carbapenem Antibiotic. Newer type. Resistant to DHP-1. Stable against Serine B-lactamases. Not against Ps. Aer. 1g/day dosing. ```

Question 30

Doripenem

Answer 30

``` Carbapenem Antibiotic. Newer type. Extremely broad spectrum. Includes anaerobes and great for Pseudomona. Only slowly hydrolyzed by DHP-1. Stable against Serine B-lactamases. IV. ```

Question 31

Bacitractin A

Answer 31

``` Bacitracin - Peptide Antibiotic Gram+ only. Topical. Often Combined w/ Polymyxin. Blocks the diphosphatase that converts Di to Mono by binding the Di with a Mg2+: it blocks translocation. ```

Question 32

Vancomycin

Answer 32

Prototypical Glycopeptide Antibiotic. Gram+ only. Usually reserved for B-lactamase resistant strains. IV. Inhib Transglycosylation and Transpeptidation; strong non-covalent complex with D-Ala-D-Ala terminus of lipid II and/or peptidoglycan.

Question 33

Telavancin

Answer 33

Glycopeptide Antibiotic. Vancomycin derivative. Added lipid tail. Multiple mechanisms.

Question 34

Dalbavancin

Answer 34

``` Glycopeptide Antibiotic. Teicoplanin derivative. Lipid tail added. NAG replaced with N,N-dimethylpropionamide. Active vs VanB. Greater potency. ```

Question 35

Oritavancin

Answer 35

Glycopeptide Antibiotic. Chlorobiphenyl derivative of chloroeremomycin. Active vs VanA and VanB

Question 36

Polymyxins/Colistins

Answer 36

Peptide Antibiotic Decapeptide - seven in the ring, three as a linear extension, which has a fatty acid tail. Detergent like. Inserts into lipid A of the LPS layer of Gram-; Gram- activity only. Fatty acid tail into lipid bilayer. Cationic head into anionic phospholipid head groups.

Question 37

Gramicidin

Answer 37

``` Peptide Antibiotic 15 linear peptides. Alternate b/w D and L. Not charged. N-term capped with formyl. C-term capped with ethanolamine. Helical structure formed. Inserts into Gram+ membranes; takes two Gramicidins to span membrane. Cytoplasmic cations escape. Topical only. ```

Question 38

Daptomycin

Answer 38

Peptide Antibiotic. Branched cyclic lipopeptide. Gram+ and MRSA. Oligomerization with Ca2+; inserts into membrane; disruption.

Question 39

Quinupristin/dalfopristin

Answer 39

Peptide Antibiotic; Streptogramins. Combo product; synergistic together. Must get within cell and appears to do so. Each binds different parts of bacterial ribosomes and block protein synthesis.