Beta-Lactam Antibiotics Flashcards by Sean Colebrook

Describe the mechanism of resistance in beta-lactam antibiotics.

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Describe the MOA of beta-lactam antibiotics.

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Name the classes of Beta-Lactam Antibiotics.

Penicillins

Cephalosporins

Monobactams

Carbapenems

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Name the classes of Penicillin Antibiotics.

Natural

β-Lactamase Resistant

Aminopenicillin

Carboxypenicillin

Acylureidopenicillin

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Name the Natural Penicillins (Brand & Generic).

Penicillin G—benzylpenicillin

Penicillin V—Phenoxymethylpenicillin

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What are the ROA’s for the natural Penicillins.

Penicillin G—IV

Penicillin V—PO

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What are the Gram(+)/(-) for Natural Penicillins?

Penicillin G—Gram(+) Potent

Penicillin V—Gram(+) Potent

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Beta-LA Resistance for Natural Penicillins

Penicillin G—Hydrolyzed

Penicillin V—Hydrolyzed

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Spectrum of Natural Penicillins

Penicillin G—Narrow

Penicillin V—Narrow

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Additional Notes for Natural Penicillins

Penicillin G—Poor amide resonance = fairly basic N

Penicillin V—Electron withdrawing group (EWG) increases bioavailability; T_1/2 = 5hrs

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Name the Beta-Lactamase Resistant Penicillins (Brand & Generic)

Staphcillin—methicillin

Unipen—naphcillin

Prostaphilin—oxacillin (X₁ = X₂ = H)

Tegopen—cloxacillin (X₁= Cl, X₂ = H)

Dynapen—dicloxacillin (X₁= X₂ = Cl)

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ROA for Beta-Lactamase Resistant Penicillins

Staphcillin—IV

Unipen—PO

Prostaphilin—PO

Tegopen—PO

Dynapen—PO

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Gram (+)/(-) for Beta-Lactamase Resistant Penicillins

Staphcillin—Gram (+)-Good

Unipen—Gram (+)-Good

Prostaphilin—Gram (+)-Good

Tegopen—Gram (+)-Good

Dynapen—Gram (+)-Good

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Additional Notes for Beta-Lactamase Resistant Penicillins

Staphcillin—More acid Labile (liable to change) than Pen G

Unipen—Most Active; mass-to-mass comparison

Prostacillin—Differ in the Halogen on Ring (EWG)
Order of increase H Stability (OCD)
↑ Acid Solubility = ↑EWG = Stable

Tegopen—Differ in the Halogen on Ring (EWG)
Order of increase H Stability (OCD)
↑ Acid Solubility = ↑EWG = Stable

Dynopen—Differ in the Halogen on Ring (EWG)
Order of increase H Stability (OCD)
↑ Acid Solubility = ↑EWG = Stable

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Name the Aminopenicillin Penicillins (Brand & Generic)

Polycillin—ampicillin (bacampicillin)

Amoxil—amoxicillin

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ROA for Aminopenicillin Penicillins

Polycillin—PO

Amoxil—PO

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Gram (+)/(-) for Aminocillin Penicillins

Polycillin—Gram (+)-Good, Gram (-)-Low

Amoxil—Gram (+)-Good, Gram (-)-Low

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Beta-LA Resistance for Aminocillins

Polycillin—Hydrolyzed

Amoxil—Hydrolyzed

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Beta-LA Resistance for Beta-Lactamase Resistant Penicillins

Staphcillin—Stable

Unipen—Stable

Prostaphilin—Good

Tegopen—Good

Dynapen—Good

Spectrum for Beta-Lactamase Resistant Penicillins

Staphcillin—Narrow

Unipen—Narrow

Prostaphilin—Narrow

Tegopen—Narrow

Dynapen—Narrow

Spectrum for Aminocillin Penicillins

Polycillin—Moderate

Amoxil—Moderate

Additional Notes for Aminocillin Penicillins

Polycillin—Prodrug-Hydro; R-isomer better for (G-)

Amoxil—2x better absorption; Less GI upset; #1

Name the Carboxypenicillin Penicillins (Brand & Generic)

Geopen—carbenicillin

Ticar—ticarcillin

ROA for Carboxypenicillin Penicillins

Geopen—PO, IV

Ticar—IV

Gram (+)/(-) for Caboxypenicillin Penicillins

Geopen—Gram (+)-Good, Gram (-)-Good Ticar—Gram (+)-Good, Gram (-)-Good

Beta-LA Resistance for Carboxypenicillin Penicillins

Geopen—Hydrolized Ticar—Hydrolized

Spectrum for Carboxypenicillin Penicillins

Geopen—Extended Ticar—Extended

Additional Notes for Carboxypenicillin Penicillins

Geopen—Racemize in Soln, Affect platelet=bleed Ticar—Req High Dose (30-40g) QD, Thiophene

Name the Acylureidopenicillin Penicillins (Brand & Generic)

Piperacil—pipericillin Azlin—azlocillin Mezlin—mezlocillin

ROA for Acylureidopenicillin Penicillins

Piperacil—IV Azlin—IV Mezlin—IV

Gram (+)/(-) for Acylureidopenicillin Penicillins

Piperacil—Gram (+)-Good, Gram(-)-Good Azlin—Gram (+)-Good, Gram(-)-Good Mezlin—Gram (+)-Good, Gram(-)-Good

Spectrum for Acylureidopenicillin Penicillins

Piperacil—Extended Azlin—Extended Mezlin—Extended

Beta-LA Resistance for Acylureidopenicillin Penicillins

Piperacil—Hydrolized Azlin—Hydrolyzed Mezlin—Hydrolyzed

Additional Notes for Acylureidopenicillin Penicillins

Piperacil—+20g QD, Bulk not close to block attack Azlin—More potent than Carbencillin, Acid Labile; Mezlo forms sulfonamide Mezlin—More potent than Carbencillin, Acid Labile; Mezlo forms sulfonamide

Name the classes of Cephalosporins

1st, 2nd, 3rd, and 4th Generation

Name the 1st Generation Cehphalosporins (Brand & Generic)

Keflin - Cephalothin Ancef - Cefazolin Keflex - Cephalexin

ROA for 1st Generation Cephalosporins

Keflin - IV Ancef - IV Keflex - PO

Gram (+)/(-) for 1st Generation Cephalosporins

Keflin - Gram (+): Good, Gram (-): Modest Anceft - Gram (+): Good, Gram (-): Modest Keflex - Gram (+): Good, Gram (-): Modest

Beta-LA Resistance in 1st Generation Cephalosporins

Keflin - Stable Anceft - Stable Keflex - Stable

Spectrum for 1st Generation Cephalosporins

Keflin - Moderate Ancef - Moderate Keflex - Moderate

Additional Notes for 1st Generation Cephalosporins

Keflin - Thiophene; R2 = Acetoxymethyl Activity Ancef - Longest T1/2; 85% Serum Protein Bound Keflex - Not metabolized (90% urine); UTI

Name the 2nd Generation Cephalosporins (Brand & Generic)

Ceftin - cefuroxime (axetil) Mefoxin - cefoxitin

ROA for the 2nd Generation Cephalosporins

Ceftin - PO, IV Mefoxin - IV

Gram (+)/(-) for 2nd Generation Cephalosporins

Ceftin - Gram (+): Good, Gram (-): Modest Mefoxin - Gram (+): Low, Gram (-): Modest

Beta-LA Resistance for 2nd Generation Cephalosporins

Ceftin - Good Mefoxin - Good

Specturm for 2nd Generation Cephalosporins

Ceftin - Moderate Mefoxin - Moderate

Additional Notes for 2nd Generation Cephalosporins

Ceftin - Prodrug-Ester; Oxime Ether in Syn; CSF Mefoxin - Anaerobes; Competitive Inhibitor