Unit 1 Flashcards
penicillin G
Natural penicillin. Very active against sensitive bacteria. Gram + only. Very acid labile. Readily hydrolyzed by B-lactamases.
penicillin V
Natural penicillin. Very active against sensitive bacteria. Gram + only. Less acid labile than penicillin V because of modification. Readily hydrolyzed by B-lactamases.
methicillin
B-lactamase Resistant Penicillin.
Less potent but more resistant.
Very acid labile.
Even more acid labile than penicillin G - side chain electron rich.
Nafcillin
B-lactamase Resistant Penicillin.
Most active of class.
Orally active.
Isoxazoyl Penicillins
B-lactamase Resistant Penicillins. Oxacillin - H, H. Cloxacillin - Cl, H. Dicloxacillin - Cl, Cl. Each are orally active. Very good resistance.
Ampicillin
Aminopenicillin. NH2 extends spectrum to Gram -. NH2 in R-form. Prodrug form Bacampicillin for GI absorption (Diarrhea, microbiome damage). Vulnerable to B-lactamase.
Amoxicillin
Aminopenicillin. NH2 extends spectrum to Gram -. Para-hydroxyampicilin NH2 in R-form. 2x as potent as ampicillin. Combine with clavulanic acid.
Carbenicillin
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.
Ticarcillin
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.
Pipericillin
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.
Azlocillin/Mezlocillin
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.
Cephalothin
Cephalosporin. First Generation. Good Gram+, Modest Gram-. Not orally active Good B-lactamase resistance; most resistant of First Gen.
Cefazolin
Cephalosporin. First Generation. Good Gram+, Modest Gram-. Parenteral. Longest t1/2 of First. Gen. Good B-lactamase resistance.
Cephalexin
Cephalosporin. First Generation. Good Gram+, Modest Gram-. Side-chain like Ampicillin. Orally active - Methyl at C-3. Good B-lactamase resistance.
Cefproxil
Cephalosporin. Second Generation. Good Gram+, Decent Gram-. Side-chain like Amoxicillin. Orally active. Good B-lactamase resistance.
Cefuroxime
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.
Cefoxitin
Cephamycin
?
Cefotaxime
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.
Ceftriaxone
Cephalosporin. Third Generation. Decent Gram+, Good Gram-. Most widely used injectable cephalosporin. Good B-lactamase resistance.
Cefepime
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.
Ceftaroline fosamil
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.
Aztreonam
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.
Clavulanic Acid
B-lactamase Inhibitor. Class One. Oxapenam. Weak broad antibacterial. Inhibits many B-lactamases. Synergistic with many B-lactams. w/ Amoxicillin = Augmentin. w/ Ticarcillin = Timentin.
Sulbactam
B-lactamase Inhibitor.
Class One.
Weak antibiotic activity.
Potentiates activity of ampicillin and carbenicillin.
Tazobactam
B-lactamase Inhibitor.
Class One.
Broad B-lactamase inhibition.
Goes with Pipericillin.
Thienamycin
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.
Imipenem
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%
Meropenem
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.
Ertapenem
Carbapenem Antibiotic. Newer type. Resistant to DHP-1. Stable against Serine B-lactamases. Not against Ps. Aer. 1g/day dosing.
Doripenem
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.
Bacitractin A
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.
Vancomycin
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.
Telavancin
Glycopeptide Antibiotic.
Vancomycin derivative.
Added lipid tail.
Multiple mechanisms.
Dalbavancin
Glycopeptide Antibiotic. Teicoplanin derivative. Lipid tail added. NAG replaced with N,N-dimethylpropionamide. Active vs VanB. Greater potency.
Oritavancin
Glycopeptide Antibiotic.
Chlorobiphenyl derivative of chloroeremomycin.
Active vs VanA and VanB
Polymyxins/Colistins
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.
Gramicidin
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.
Daptomycin
Peptide Antibiotic.
Branched cyclic lipopeptide.
Gram+ and MRSA.
Oligomerization with Ca2+; inserts into membrane; disruption.
Quinupristin/dalfopristin
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.
