Med Chem - Intro + Sulfa Flashcards

(54 cards)

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

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

A

47

infections

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

who and what year was penicillin discovered

A

1929
alexander fleming

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

true or false

penicillin is not a natural product

A

FALSE

it is a natural product derived from penicillium mold

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

name 4 subclasses of beta lactams

A

penicillins
cephalosporins
carbepenems
monobactams

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

macrolides and ______ are structural cousins

A

ketolides

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

true or false

quinolones are synthetic

A

true

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

lincosamides are _____ containing

A

sulfur

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

structural derivatives of tetracyclines
what makes them better

A

glycylcyclines

they have better resistance profile

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

2 glycopeptides

A

vancomycin and daptomycin

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

what class is gramicidin

A

peptide class

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

true or false

streptogramins are 2 components combined

A

true

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

sulfa drugs are derivatives of…..

A

p-aminobenzene sulfonamides

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

are sulfa drugs bacteriostatic or cidal?

A

static

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

is spectrum of sulfa drugs broad or narrow spectrum

A

broad

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
18
Q

true or false

sulfa drugs were once used wisely but not as much anymore

A

true

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

what year were sulfa drugs discovered

A

1935

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
20
Q

what is the simplest sulfa drug

A

sulfanilamide

the R substituion is just an H

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

24
TYPICALLY, aliphatic amines are considered acidic, neutral, or basic?
basic
25
when N connected to sulfonyl as in the case of sulfonamide, is it acidic, neutral, or basic?
NEUTRAL, but polar behaves like carboxamide
26
azo gets bioreduced to....
amine (NH2)
27
name 4 precursors that depend on bioreduction to get activated to a primary amine for sulfonamide activity
azo (N=N) nitro (NO2) -NHOH -N=O (nitroso) carboxamide depends on HYDROLYSIS
28
main MOA of sulfonamides
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
what does PABA stand for
p-aminobenzoic acid
30
differentiate between the durations of different sulfonamides WHICH IS IDEAL
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
Name the sulfonamides in the short/medium acting (6-12 hours) class
sulfisoxazole sulfacetamide sulfadiazine sulfamethoxazole
32
name the sulfonamides in the long acting class (20-40 hours)
sulfamerazine
33
name the sulfonamides in the ultra long acting class (100-200 hours)
sulfalene
34
give a scenario in which the ultra long acting sulfonamides may actually be beneficial
cases of war where you can't really get meds on a regular basis
35
2 drugs used for burn therapy
mafenide (NOT A TRUE SULFONAMIDE - DOES NOT FOLLOW SULFONAMIDE SAR) silver sulfadiazine - is a sulfonamdie
36
silver sulfadiazine
a sulfonamide silver salt used for external application for burns
37
true or false mafenide is not antagonized by PABA
TRUE it's not a true sulfur drug
38
2 trade names of trimethoprim-sulfamethoxazole
bactrim septra
39
structurally, what is trimethoprim
a diamonopyrimidine
40
true or false trimethoprim is bactericidal
FALSE both trimethoprim and sulfamethoxazole are bacteriostatic when used alone, BUT CIDAL WHEN COMBINED -- SYNERGY
41
what does trimethoprim inhibit
MICROBIAL dihydrofolate reductase (DHFR) humans have this enzyme, but trimethoprim has 100,000-fold selectivity for the BACTERIAL enzyme
42
mafenide is _____-acting and ____ spectrum
short acting and broad spectrum
43
true or false mafenide is not an active antibiotic
FALSE - it is - just not a true sulfonamdie
44
true or false it is hard for bacteria to develop resistance to bactrim
TRUE 2 different steps are being attacked
45
what route are sulfonamides usually admjinisterd
orally
46
true or false sulfonamides do not cross the placenta or blood brain barrier
FALSE it crosses both readily
47
true or false sulfonamides are highly protein bound
true
48
name all the ways that sulfonamides are aexcreted
-parent (not metabolized) -N4-acetate (acetylated) -glucuronides
49
sulfonamides can cause renal crystalluria explain the logic behind this
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
what is the "triple sulfa" method
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
aside from the triple sulfa method, name other methods to overcome the metabolite water insolubility issue with sulfonamides
-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
aside from renal crystalluria, name 3 other concerns with sulfonamides
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