Brainscape's Knowledge GenomeTM


Top Flashcards (Certified)
All Flashcards

z F1: Med Chem > Exam 1 > Flashcards

Exam 1 Flashcards

(76 cards)

Start Studying
1
Q

What are the principles on which modern drug development and discovery is based

A

Absorption: how much gets into body
Distribution: where drug ends up
Metabolism: body deal with substance
Excretion: how much it gets rid of
Toxicity: will it hurt

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

High protein binding drugs are __________ drugs

A

lipophilic

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

Consequence of high protein binding is

A

drug-drug interactions

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

Consequence of hERG

A

drugs bind to hERG can cause fatal arrhythmias

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

The behavior of all drugs is determined by their chemical properties which is due to their _________ ______

A

functional groups

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

Drugs get the _____ number on alicyclic rings

A

lowest, the substituents are then counted lowest from there

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

The three most common heteroatoms in drugs are

A

N, S, O
highest priority is based on molecular weight

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

Alpha and Beta are used to indicate a carbon atom that is adjacent to _____

A

C=O or a heteroatom

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

Omega is used to indicate the ____ of an alkyl chain

A

end

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

On a molecule which side is the alpha side and which is the beta side

A

Beta side is on top with bold lines
Alpha side on the bottom with dashed lines

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

The same functional group can serve _______ roles depending on the location in the drug

A

different

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

Each functional group can serve _____ roles at the same time

A

several

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

What are the three major chemical properties to consider when evaluating functional groups

A

Electronic effect (electron withdrawing or donating)
Solubility
Steric (how big is it)

-Each functional group effects all of the factors
-The overall effect of each group depends on other functional groups surrounding it

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

Negatively charged groups can donate electrons through

A

induction

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

Functional groups with a lone pair can donate electrons through

A

resonance

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

alkyl groups can donate electrons through

A

induction

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

Electron withdrawing groups

A

positive charged groups can pull e- via induction
When alcohol, ether, thiol groups are NOT adjacent they are EWG
Halogens are withdrawing groups

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

Solubility effects are based on the ability of a functional group to

A

Enhance interactions with water (hydrophobic or lipophilic)
Enhance interactions with lipids (hydrophobic or lipophilic)

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

What two major properties enhance the water solubility of a functional group

A

the ability to ionize (atom to become charged)
ability to form hydrogen bonds

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

Acids donate their protons ____ water
Bases accept protons ____ water

A

Acids: to
Bases: from

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
21
Q

Prototype for determining interactions with the aqueous environment, through the interaction of hydroxyls to form _______

A

H-bonds

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
22
Q

General points for alcohols groups: ____ participate in IMF, ____ interact with with water

A

can
can

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
23
Q

While the alcohol group interacts well with a water molecule, the overall stability of ROH is dependent on the _____ of the hydrocarbon side chain attached to that alcohol ________

A

size
R-group

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
24
Q

The ________ effects of the carbons will counteract the __________ effects of the alcohol

A

hydrophobic
hydrophilic

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
25
As the length of the hydrocarbon side chain alcohol group increases, the _________ nature of the molecule decreases
hydrophilic
26
In thiols the S atom is ______ than O atom so it can better stabilize a negative charge
larger
27
Thiols can be ________ especially if attached to an aromatic ring or in an enzyme active site
ionized
28
The ability of the thiol SH to H-bond is ______ than an alcohol
weaker, they are not as polar
29
Can ketones and aldehydes h-bond, are they polar
yes yes due to carbonyl
30
Esters increased _______ over the both alcohol and acid parent, but still polar due to dipole of the carbonyl and oxygen in the functional group
lipophilicity
31
Esters can be used to _______ absorption following oral admin of some drugs, relies on hydrolysis of ester to release active form in the blood stream
increase
32
Are amides ionizable groups in the body? If so are they acids or bases and why?
Not readily ionizable because resonance prevents ionization amides have carbonyl and amines do not lone pair of nitrogen is not available = not a base
33
Amides
-found in peptides -less lipid solubility than esters (more hydrophilic) -high degree of H-bonds -As hydrocarbon portion of amide increases so does lipophilic nature
34
Carbamates
fusion between an amide and an ester behave more like an amide than an ester
35
Ureas
look like a fusion between 2 amides properties similar to amides, perhaps a bit more polar
36
Ethers
H-bond acceptor form weak H-bonds from O more polar than alkane
37
Cyclic ethers
locks in 109 degree and enhance dipole, more polar as result
38
Lipophilicity ______ as the number of carbons increase
increases
39
Non polar functional groups lack to ability to _______ and ________
ionize and H-bond
40
Alkyl groups (ethyl, methyl etc)
Are the most lipophilic of the functional groups increase size = increase lipophilicity
41
Alkenes, aromatic groups, heteroaromatic compounds
Have pi system, allows for induction Interact with similar groups on target molecules Can be substituted with heteroatoms, remain aromatic
42
Halides
-Hydrophobic -Electron withdrawing increases as size of atom decreases -Effect on pKa when added carbons adjacent to acid/base functional groups
43
Fluorine halide
size=hydrogen atom used in place of hydrogen to increase a dipole
44
Chlorine halide
larger in size than fluorine, 1/2 that of methyl improve interaction of an aromatic group with an aromatic binding site or to block metabolism on aromatic groups
45
Bromine halide
larger than chlorine, smaller than methyl improve interaction of aromatic group, block metabolism on aromatic groups
46
Iodine halide
size=methyl mimix a methyl group in size, but have an opposite electronic effect than methyl
47
Nitroesters, nitrates, nitrogroups on alkanes
similar to halides
48
functional groups that are ______ will have the strongest interaction with water, and the least with a lipid
charged
49
functional groups that are polar but can't h-bond will have properties __________ aqueous and lipid loving
in between
50
combining a polar functional group with a number of atoms of a non-polar functional group will result in a ________ of properties for the ______ molecule
composite whole
51
Key features of acids
The presence of a hydrogen that can dissociate to form a proton The ability of the other atoms to delocalize the resulting negative charge (via resonance)
52
The ionized form of a carboxylic acid is known as a _________
carboxylate
53
If the R group is electron withdrawing it will stabilize the _____ and increase its _________
anion acidity
54
non-ionized carboxylic acid general points
-carboxylic acids are polar and can hydrogen bond when in protonated form -are more polar than alcohols and will provide stronger interaction -increase R-group length decreases water solubility and increases lipid solubility
55
Are the majority of drugs in a ketone or enol form
enol
56
The imide is an example of a(n) ______ nitrogen
acidic
57
When groups have a similar shape, size, and electron density, they are ________ of each other
bioisosteres
58
A regular alcohol has no resonance stabilization and therefore can not ________
ionize
59
How many acidic protons does phosphonic acid have
2
60
What is a key feature of a base
presence of a lone pair that can accept a proton *ability of electrons to accept proton makes it stronger
61
Steric bulk of groups _____ access to lone pair
hinder -makes it more acidic
62
Amines general points
-solubilize drugs as the free base or as water soluable slat of amine -hold drug to target -alkaline
63
Why are aromatic amine less basic than aliphatic amines
Lone pair gets pulled into aromatic ring contributing to resonance while aliphatic can give lone pair to carbon
64
What are amphoteric molecules
contain both acidic and basic functional groups
65
Protonation occurs on the ___ hybridized nitrogen
sp2
66
Sulfanaminde, sulfonyl urea, imide, tetrazole
acidic nitrogen containing functional groups
67
amide, carbamate, urea, pyrrole, indole
neutral nitrogen containing funcitonal groups
68
ionization = charge = ________ water solubility
increase
69
________ drugs are more readily reabsorbed increasing their half life in body
neutral
70
The degree to which acidic and basic functional groups are ionized depends on the ____ of the functional group in question and on the _____
pka pH
71
pKa provides no information about _____ a molecule will ionize. It will only indicate the degree to which it will occur
how
72
When pH=pKa the solution ...
50% acid and 50% base
73
When pH is below the pKa
acid (neutral) > base (ionized) protonated form > deprotonated form
74
When pH is above pKa
base (ionized) > acid (neutral) deprotonated > protonated
75
AID your BUDdy
pH higher than pKa acidic functional group, ionized form dominates basic functional group, unionized form dominates
76
BID on the AUDience
pH lower than pKa basic functional group, ionized form dominates acidic functional group, unionized form dominates

z F1: Med Chem (3 decks)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2025 Bold Learning Solutions. Terms and Conditions