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D&D Infectious Disease Midterm > Med Chem - Intro + Sulfa > Flashcards

Med Chem - Intro + Sulfa Flashcards

1
Q

true or false

the development of drugs to treat infectious disease is one of the most important advances in the history of medicine

A

TRUE

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2
Q

what was the life expectancy in 1900 and what was the leading cause of death

A

47

infections

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3
Q

what year and event marked the birth of anti-infective chemotherapy

A

1911

Paul Erlich showed that arsphenamine (salvarsan) was active for syphilis in an experimental rabbit model

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4
Q

as mentioned, in 1911 marked the birth of anti-infective chemotherapy when paul erlich should salvarsan/arsphenamine was active for syphilis in an experimental rabbit

what did Ehrlich do next?

A

he introduced the concept of systemic screening

this lead to the discovery of sulfa drugs by bayer chemists

later, systemic screening became the cornerstone of strategies of searching for drugs

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5
Q

who and what year was penicillin discovered

A

1929
alexander fleming

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6
Q

true or false

penicillin is not a natural product

A

FALSE

it is a natural product derived from penicillium mold

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7
Q

name 4 subclasses of beta lactams

A

penicillins
cephalosporins
carbepenems
monobactams

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7
Q

why were antimicrobial advances in discovering sulfa drugs and penicillin perfectly timed?

A

bc they helped in ww2

death from sepsis had previously been an almost certain consequence following injury

with the discovery of antibiotics (specifically sulfa and penicillin), it became avoidable

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8
Q

macrolides and ______ are structural cousins

A

ketolides

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9
Q

true or false

quinolones are synthetic

A

true

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10
Q

lincosamides are _____ containing

A

sulfur

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11
Q

structural derivatives of tetracyclines
what makes them better

A

glycylcyclines

they have better resistance profile

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12
Q

2 glycopeptides

A

vancomycin and daptomycin

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13
Q

what class is gramicidin

A

peptide class

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14
Q

true or false

streptogramins are 2 components combined

A

true

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15
Q

sulfa drugs are derivatives of…..

A

p-aminobenzene sulfonamides

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16
Q

are sulfa drugs bacteriostatic or cidal?

A

static

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17
Q

is spectrum of sulfa drugs broad or narrow spectrum

A

broad

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18
Q

true or false

sulfa drugs were once used wisely but not as much anymore

A

true

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19
Q

what year were sulfa drugs discovered

A

1935

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20
Q

what is the simplest sulfa drug

A

sulfanilamide

the R substituion is just an H

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21
Q

explain what sulfanilamide is

A

its prodrug is PROTONSIL

protonsil gets bioreduced to form its ACTIVE METABOLITE - sulfanilamide

22
Q

why is protonsil not used anymore

A

when it gets bioreduced to produce sulfanilamide, the N=N is clipped

the biproduct is polyamino benzene, which is a potent carcinogen

23
Q

name for N=N

A

azo

24
Q

TYPICALLY, aliphatic amines are considered acidic, neutral, or basic?

A

basic

25
Q

when N connected to sulfonyl as in the case of sulfonamide, is it acidic, neutral, or basic?

A

NEUTRAL, but polar

behaves like carboxamide

26
Q

azo gets bioreduced to….

A

amine (NH2)

27
Q

name 4 precursors that depend on bioreduction to get activated to a primary amine for sulfonamide activity

A

azo (N=N)
nitro (NO2)
-NHOH
-N=O (nitroso)

carboxamide depends on HYDROLYSIS

28
Q

main MOA of sulfonamides

A

inhibit dihydropteroate synthase

(the enzyme that catalyzes the conversion of PABA + dihydropteroate diphosphate to dihydropteroic acid which ic converted to THF, thymine, and then DNA)

29
Q

what does PABA stand for

A

p-aminobenzoic acid

30
Q

differentiate between the durations of different sulfonamides

WHICH IS IDEAL

A

short/medium acting (t1/2 6-12 hours)

long acting (t1/2 20-40 hrs)

ultra long acting (t1/2 100-200 hours)

6-12 hours (short-medium acting) IS IDEAL

31
Q

Name the sulfonamides in the short/medium acting (6-12 hours) class

A

sulfisoxazole
sulfacetamide
sulfadiazine
sulfamethoxazole

32
Q

name the sulfonamides in the long acting class (20-40 hours)

A

sulfamerazine

33
Q

name the sulfonamides in the ultra long acting class (100-200 hours)

A

sulfalene

34
Q

give a scenario in which the ultra long acting sulfonamides may actually be beneficial

A

cases of war where you can’t really get meds on a regular basis

35
Q

2 drugs used for burn therapy

A

mafenide (NOT A TRUE SULFONAMIDE - DOES NOT FOLLOW SULFONAMIDE SAR)
silver sulfadiazine - is a sulfonamdie

36
Q

silver sulfadiazine

A

a sulfonamide silver salt used for external application for burns

37
Q

true or false

mafenide is not antagonized by PABA

A

TRUE

it’s not a true sulfur drug

38
Q

2 trade names of trimethoprim-sulfamethoxazole

A

bactrim
septra

39
Q

structurally, what is trimethoprim

A

a diamonopyrimidine

40
Q

true or false

trimethoprim is bactericidal

A

FALSE

both trimethoprim and sulfamethoxazole are bacteriostatic when used alone, BUT CIDAL WHEN COMBINED – SYNERGY

41
Q

what does trimethoprim inhibit

A

MICROBIAL dihydrofolate reductase (DHFR)

humans have this enzyme, but trimethoprim has 100,000-fold selectivity for the BACTERIAL enzyme

42
Q

mafenide is _____-acting and ____ spectrum

A

short acting and broad spectrum

43
Q

true or false

mafenide is not an active antibiotic

A

FALSE - it is - just not a true sulfonamdie

44
Q

true or false

it is hard for bacteria to develop resistance to bactrim

A

TRUE

2 different steps are being attacked

45
Q

what route are sulfonamides usually admjinisterd

A

orally

46
Q

true or false

sulfonamides do not cross the placenta or blood brain barrier

A

FALSE

it crosses both readily

47
Q

true or false

sulfonamides are highly protein bound

A

true

48
Q

name all the ways that sulfonamides are aexcreted

A

-parent (not metabolized)
-N4-acetate (acetylated)
-glucuronides

49
Q

sulfonamides can cause renal crystalluria

explain the logic behind this

A

as mentioned, it’s excreted as parent, N4 acetate, and glucuronides.

therefore, 2/3 is excreted as the parent molecule and N4 acetate – which are not necessarily water soluble

this can cause renal crystalluria – can precipitate out
(advise pt to stay hydrated!!!)

50
Q

what is the “triple sulfa” method

A

old method used to try to enhance water solubility of sulfonamides and prevent renal crystalluria

combines 1/3 of 3 different sulfonamides (sulfadiazine, sulfamerazine, and sulfamethazine) with the idea that their water solubilities will combine to enhance water solubiliy

51
Q

aside from the triple sulfa method, name other methods to overcome the metabolite water insolubility issue with sulfonamides

A

-take or instill bicarbonate to enhance urine flow

-substitute the sulfonamide for one with a lower pka (6-7) – like sulfamethoxazole! so this isn’t really concern anymore

52
Q

aside from renal crystalluria, name 3 other concerns with sulfonamides

A

hypersensitivity - can cause SJS (erythema multiforme)

kernicterus (brain damage caused by hyperbilirubinemia) so CONTRAINDICATED IN PREGNANT WOMEN
bb’s have lack of glucuronidation and competition for plasma proteins – sulfonamides bind to same binding site as bilirubin – can displace

can cause hypoglycemic shock by interfering with the excretion of oral hypoglycemics for diabetes

53
Q
A

D&D Infectious Disease Midterm (26 decks)

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