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D&D Infectious Disease Midterm > Med Chem - B lactamase inhibitors + Carbapenems + Monobactams > Flashcards

Med Chem - B lactamase inhibitors + Carbapenems + Monobactams Flashcards

1
Q

name 4 combination products that contain a beta lactamase inhibitor

A

augmentin
unasyn
sulperazone
sultamicillin

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2
Q

augmentin

A

amoxicillin + clavulanic acid

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3
Q

sulperazone

A

cefoperazone + sulbactam

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4
Q

sultamicillin

A

ampicillin + sulbactam
(another brand for unasyn)

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5
Q

Unasyn

A

ampicillin + sulbactam
(another brand for sultamicillin)

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6
Q

name 5 beta lactamase inhibitors

which 2 do NOT structurally mimic beta lactam antibiotics

A

clavulanic acid
sulbactam
tazobactam
avibactam
valorbactam

avibactam and valorbactam do not structurally mimic beta lactam

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7
Q

which beta lactamase inhibitor contains boron

A

valorbactam

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8
Q

in general, which are more resistant to beta lactamases – penicillins or cephalosporins?

A

cephalosporins, especially higher generations (3rd) have built in resistance

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9
Q

true or false

beta lactamase inhibitors target PBP

A

false

THEY HAVE NO ANTIBACTERIAL PROPERTIES

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10
Q

what was the natural starting point with carbapenems and what were the issues with it

A

thienamycin

had chemical and enzymativ instability

chemical instability in the side chain. terminal NH3+ is electron withdrawing, causing the beta carbon to sulfur to be e- deficient and electrophilic. this will cause sulfur to attack the beta carbon and the reaction will occur because NH3+ is a good leaving group. side chain spontaneously falls apart

enzymatic instability because the beta lactam ring is hydrolyzed by a human renal enzyme called DHP1

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11
Q

imipenam

A

chemical instability of thienamycin was fixed by adding a terminal atom.
however, enzymatic instability still there

to fix, was combined with CILASTATIN which protects imipenem from hydrolysis

THIS COMBINATION PRODUCT OF IMIPENEM + CILASTATIN IS CALLED PRIMAXIN

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12
Q

meropenem

A

fixed both issues of thienamycin

no chemical instability because while sulfur and N are still 2 atoms apart, the N is part of a cyclic ring for addtional protection

no enzymatic instability because a METHYL GROUP was added onto the 5 membered ring, providing DHP-1 resistance

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13
Q

what can meropenem be combined with and what is the brand name of this combination product

A

meropenem + vaborbactam
called VABOMERE

vaborbactam is a non beta lactam, boron containing beta lactamase inhibitor.it enhances the action of meropenem by protecting it from certain serine B-lactamases like klebsiella pneumoniae carbapenemase

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14
Q

true or false

vaborbactam does not have any antibacterial activity

A

TRUE

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15
Q

the vaborbactam component of vabomere is a ________ ________ inhibitor that protects meropenem from degredation

A

non-suicidal beta lactamase inhibitor

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16
Q

what was the 1st successful carbapenem that fixed both issues of thienamycin (chemical and enzymatic instability

A

meropenem

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17
Q

name 4 carbapenems

what was natural prototype

A

natural prototype = thienamycin

meropenem
imipenem
etrapenem
doripenem

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18
Q

which has more hydrophilic substituents and which has more lipophilic substituents between doripenem and etrapenem

A

etrapenem has more lipophilic

doripenem has more hydrophilic

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19
Q

structurally, what are monobactams

A

monocyclic beta lactams

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20
Q

1 and only example of a monobactam

A

aztreonam

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21
Q

how are monobactams able to have sufficient beta lactam activity, without the beta lactam ring being fused with another ring?

A

the sulfate substituent (SO3-) gives the structure necessary beta lactam activation

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22
Q

quinolones are bactericidal or static??

explain

A

rapidly bactericidal

bc they inhibit DNA gyrase (topoisomerase II) and topoisomerase 4 which are key enzymes for dictating the conformation of DNA

23
Q

why do we say fluoroquinolones have a unique mechanism of action

A

their target is inside the bacteria

24
Q

explain the progressive discovery of fluoroquinolones

A

started with nalidixic acid (not a true quinolone)

structurally modified to oxolinic acid – a true quinolone, but still not good enough

NORFLOXACIN was created, which is considered the prototype for 2nd gen quinolones (aka fluoroquinolones) has a fluorine at the 6 position which is a universal characteristic of 2nd gen quinolones (fluoroquinolones)

25
Q

name 3 macrolides

A

erythromycin
azithromycin
clarithromycin

26
Q

explain the chemical structure of macrolides

A

large (14-15 membered) lactone ring with a glycosidically linked amino sugar

27
Q

MOA of macrolides

A

protein synthesis inhibitor

by binding to 50s ribosomal subunit

bacteriostatic

28
Q

3 SAR components for macrolides

what was the prototype?

A

prototype was erythromycin

decosamine
cladinose
lactone (ester linkage in cyclic form)

29
Q

name a ketolide

A

telithromycin

30
Q

which has a lower incidence of developing resistance and why - macrolides or ketolides?

A

ketolides because of the switch from 3-cladinose to 3-ketone in ketolides

thus, methylase gene expression of bacteria does NOT induce resistance

31
Q

true or false

telithromycin is for oral administration

A

true

32
Q

MOA of ketolides

A

same as macrolides

inhibit protein synthesis by binding 50s ribosomal subunit

33
Q

explain the characteristics of fidaxomicin

A

macrocyclic, but NOT a macrolide because there has to be a cyclic ester and amino sugar but fidaxomicin does NOT have an amino sugar

extremely narrow spectrum and administered orally for c diff infection

34
Q

MOA fidaxomicin

A

inhibits bacterial RNA polymerase

SELECTIVELY eradicates c diff with minimal dectruction to healthy flora

35
Q

fidaxomicin is _____ derived

A

NATURALLY

36
Q

fidaxomixin is part of a new class of ______ spectrum ____ antibiotics

A

narrow spectrum macrocyclic antibiotics
(but NOT a macrolide - no amino sugar)

37
Q

bezlotoxumab

A

human monoclonal antibody designed to prevent the recurrence of c diff infection

38
Q

name 2 lincosamides

A

lincomycin
clindamycin

39
Q

lincosamides are ____ containing

A

sulfur

40
Q

MOA lincosamides

include whether bacteriostatic or cidal

A

bacteriostatic protein synthesis inhibitors

binds 50s subunit (same as macrolides - remember MLS)

41
Q

name 6 aminoglycosides

A

tobramycin
neomycin
kanamycin
amikacin
streptomycin
gentamicin

42
Q

MOA aminoglycosides

cidal or static?

A

bactericidal

binds 30s ribosomal subunit

43
Q

true or false

aminoglycosides are primarily active against gram (+)

A

FALSE

gram (-)

44
Q

how are aminoglycosides administered and why

A

parenteral or topical - NOT ORAL

bc of basic alkyl amines

45
Q

concerns with aminoglycosides

A

because of basic character, can have strong ionic interaction with anions in otic and renal compartments, causing otic and renal toxicitiy

46
Q

MOA tetracyclines

static or cidal?

A

static

binds 30s subunit

47
Q

clinical concerns with tetracyclines

A

under 8 yrs old - permanent teeth staining

also drug drug interaction with metal ions - *milk, iron, antacids

48
Q

briefly explain structure of tigecycline

A

minocycline + 9-glycylamido moeitiy

this 9-glycyl amido gives it enhanced activity

49
Q

MOA tigecycline

A

same as tetracycline

bacteriostatic - binds 30s subunit, blocking entry of amino-acyl tRNA into A site of ribosome

50
Q

color of tigecycline

A

oragee

51
Q

differentiate between resistance of tetracycline vs tigecycline

A

tigecycline has less resistance bc not affected by ribosomal protection or efflux of the drug (while tetracyclines are susceptible to these)

52
Q

2 tetracycline derivatives and name the difference (structurally)

A

tigecycline and eravacycline

tigecycline has addition of 9-glycylamido moeity on minocycline

eravacycline has 2 changes. fluorine atom at C7 and pyrrolidinoacetamido on C9 (both on D ring!!)

BOTH have better resistance profile

53
Q
A

D&D Infectious Disease Midterm (26 decks)

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