(SAR) M6 - Fluoroquinolones and Penicillins

What is the name of this structure?

Chloroquine

What is the name of this structure?

7-chloroquinoline

What are the significance of the carbonyl and carboxyl groups on this structure?

Reduce protein binding

What is the name of this structure?

Nalidixic acid

What group was added to 7-chloroquinoline for it to become this structure?

Naphthyridone

What is the name of this group?

Naphthyridone

What is the name of this structure?

Flumequine

This structure is flumequine, what is it’s other name?

Benzo-quinolizine

Flumequine exhibits weak but broad ___ activity

Gram negative

What is the name of this structure?

Pipemidic acid

What ring was added to the structure to form pipemidic acid?

Piperazine ring

This structure is pipemidic acid, what is its other name?

pyrido-2,3-pyrimidine

Pipemidic acid exhibits longer _____

half life

What is the name of this structure?

Norfloxacin

This structure is norfloxacin, what is its other name?

6-fluoro-7-pyrimidino-quinoline

Norfloxacin exhibits broader ______ activity, less protein binding (__%), and longer half-life (____ hrs)

gram negative, 50%, 3-4

what is the name of this structure?

Pefloxacin

What was added to the norfloxacin to form pefloxacin?

Methyl group

Pefloxacin exhibits an even longer _____

half life

What is the name of this structure?

Ofloxacin

What was added in pefloxacin to create this compound?

Morpholine ring

What is the name of this ring?

Morpholine ring

What is the name of this structure?

Ciprofloxacin

Ciprofloxacin exhibits an increased ____

potency

What was added to norfloxacin to create this structure?

cyclopropyl ring

What is the effect of the substituent at R5?

Enhance activity against gram positive

What is the effect of the substituent at R7?

enhance activity against gram negative

What is the effect of the modification at X8?

enhance activity against gram positive and anaerobes

What is the effect of the substituent at R1?

Enhance activity against gram positive and negative, increase potency

What is the effect of the substituent at R5?

enhance activity against gram negative

What is the effect of the substituent at R7?

enhance activity against gram positive

What is the effect of the modification at X8?

increase potency

What is the effect of the substituent at R1?

enhance activity against anaerobe, increase potency

What is the effect of the substituent at R5?

enhance activity against gram positive

What is the effect of the substituent at R7?

increase half life

what is the effect of the modification at X8?

enhance activity against gram positive, negative, and anaerobe; increase potency

what is the effect of the substituent at R1?

enhance activity against gram positive and negative, increase potency

What is the name of this ring?

Beta-lactam ring

What is the name of this structure?

6-aminopenicillanic acid

What is the name of the substituent in Box A?

Acylamino side chain

What is the name of the structure indicated at “B."?

Thiazolidine ring

What is the effect of this modification on its activity?

decrease activity

What is the name of this structure?

Penicillin G

This structure is penicillin G, what is its other name?

Benzylpenicillin

The salt form of this structure would increase what?

Lipophilicity

What is the name of this structure?

Penicillin V

This is penicillin V, what is its other name?

Phenoxymethylpenicillin

What was added to the structure to penicillin V to make it acid stable?

electronegative oxygen

What is the name of this structure?

Methicillin sodium

What is the name of this structure?

Nafcillin sodium

What is the name of the group enclosed in the box?

Isoxazoyl group

Are isoxazoyl penicillins acid resistant and beta lactamase resistant?

Yes

What is the name of this structure?

Cloxacillin

What is the name of this structure?

Oxacillin

What is the name of this structure?

Flucloxacillin

What is the name of this structure?

Dicloxacillin

Because this structure has hydrophobic groups what is the effect on gram (+) activity?

Increase

Because this structure has hydrophobic groups what is the effect on gram (-) activity

Poor

Because this structure has an increased hydrophobic character what is its effect on gram (-) activity?

Significantly reduced

Because this structure has an increased hydrophobic character what is its effect on gram (+) activity?

Decrease

Because this structure have hydrophilic groups on the side chain what is the effect on Gram (+) activity?

Reduced

Because this structure have hydrophilic groups (-NH2) on the side chain what is the effect on Gram (-) activity?

Increase

What is the name of this structure?

ampicillin

What makes this structure acid-stable?

amino group

What is the name of this structure?

Amoxicillin

What makes amoxicillin have better absorption over ampicillin?

hydroxyl group

What is the name of this structure?

Carbenicillin disodium

What makes this structure have better penetration towards Gram (-)?

Ionizable carboxyl group

What is the name of this structure?

Carbenicillin indanyl sodium

What is the name of this group?

Urea

What is the name of this structure?

Mezlocillin sodium

what is the name of this structure?

Piperacillin

What does mezlocillin and piperacillin have that allows them to eliminate pseudomonas aeruginosa?

Urea at alpha position