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PHRM 824 Final > Exam 1 Material > Flashcards

Exam 1 Material Flashcards

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1
Q

Any substance that brings about a change in biologic function through its chemical actions

A

Drug

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2
Q

To modulate the biological activity of a receptor, a drug needs to

A

move to the location of the receptor and bind to it

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3
Q

A similar structure motif that drugs bind to when they bind to the same target, set of features similar between a group of molecules

A

Pharmacophore

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4
Q

Examples of pharmacophore

A

Fentanyl, naloxone, morphine

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5
Q

Structure activity relationship

A

Structure determines activity, can determine binding and membrane permeability

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6
Q

Properties determined from structure

A

Stereochemistry, solubility, ionization, hydrophobicity, size

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7
Q

Properties that affect biological activities

A

Permeability, target binding, metabolism, excretion

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8
Q

Drug property affected by pH

A

ionization

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9
Q

Ionizable groups

A

Arylcarboxylic acid, arylamine, aromatic amine, alkyl carboxylic acid, alkyl amine, phenol, guanidine

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10
Q

Henderson hasselbach equation

A

pH=pKa+log [A]/[HA]

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11
Q

pH < pKa

A

protonated

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12
Q

pH > pKa

A

deprotonated

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13
Q

At pH 6.4 what is the ratio of drug in acid form to base form? pKa is 4.4

A

6.4=4.4+Log A/HA
=2 move 2 zeros
1:100
deprotonated, more base than acid

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14
Q

Modes of drug permeation into body

A

Intercellular junctions
Lipid cell membranes
Transporters
Endocytosis
Exocytosis

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15
Q

Hydrophilic groups

A

Alcohol, carboxylic acid, amine, ketone, amide, ester

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16
Q

Hydrophobic

A

Methyl, chloro, phenyl, hexyl, cyclohexyl

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17
Q

Less OH means more

A

hydrophobic

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18
Q

H bond donors

A

OH, NH

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19
Q

H bond acceptors

A

O, N

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20
Q

Lipinski’s rule of 5

A

Describes orally active drugs
No more than 5 H bonds
No more than 10 H acceptors
Molecule mass less than 500
LogP under 5

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21
Q

Predict effect of a structural change in a drug on its solubility in water

A

Lose OH, may no longer be soluble/orally active

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22
Q

LogP <0 favors ?

A

Water

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23
Q

LogP = 0 ?

A

Equal distribution

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24
Q

LogP > 0

A

Favors 1 octanol

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25
bigger logP means
More hydrophobic
26
Explain why the relationship of drug effectiveness vs LogP is parabolic
Lipophilicity improves drug permeation but too much may hinder crossing
27
Calculate ClogP
Sum of Pi values lower number means more acidic
28
Estimate LogD
LogD = LogP - (pH-pKa) When pH is bigger than pKa it is first in equation
29
When are drugs most absorbed?
Where they are mostly neutral
30
Location with pH of 5-7
jejunum and duodenum
31
Location with pH 6-8
Illium
32
Location with pH 1-3
stomach
33
Can a quaternary amine be absorbed?
No, tubocurarine fine to eat not orally available
34
What makes electronic effects weaker
going through multiple bonds
35
Positive sigma value
Electron withdrawing, more acidic, lower pKa
36
Negative sigma value
electron donating, less acidic, higher pka
37
Meta position
diagonal
38
Para position
across
39
Ortho position
next to
40
Resonance effect
Ortho and para positions Through pi bonds
41
Inductive effect
Ortho and para positions Through sigma bonds
42
Only inductive effect
Meta position
43
electron donating
Negative sigma value, increase pKa, decrease acidity
44
Electron withdrawing
Have unshared electron pair, ortho para directing
45
Fluorine characteristic
Metabolism resistant
46
Isoteres
similar shapes and electronic effects H and F
47
Stereoisomers
Mirror images, 1+ chiral centers, same properties except for optimal rotation
48
R/S
Absolute configuration, 3D arrangement, primary method
49
d/l
Optimal rotation, experimentally determined, dependent on solution conditions
50
D/L
Relative configuration to glyceraldehyde, only for amino acids and sugars
51
S notation
Counter clockwise
52
R notation
clockwise
53
The more potent
the more interactions with receptors needed
54
List factors other than receptor binding that result in different biological properties of drug enantiomers
Permeation by transporters Nonspecific binding to serum proteins Metabolism
55
Issues of racemic drugs
Separation is difficult and costly inactive is physiologically inert
56
Enantiomers
non superimposable mirror images
57
Diastereomers
not mirror images
58
Geometric isomers
have double bonds cis z and trans e
59
KD value at 1
100% occupied
60
KD value at 0
0% occupied
61
DeltaGD=-RTlnKD
R = gas constant 8.314 T = temp in kelvin
62
Change in KD from deltaGD
Reduce KD 10 fold, add 1.4 to G
63
Hydrophobic interactions
Between nonpolar groups in water
64
Electrostatic interactions
+ and - , long distances
65
Hydrogen bonding
O and N with H in middle
66
Aromatic ring interactions
Faces electron rich Edges electron deficient Pi stacking, T stacking
67
Atorvastatin and HMG-CoA reductase
Hydrophobic interaction
68
QSAR
Mathematical, correlation between structure and activities Derived by statistical regression Receptor info not needed
69
QSAR structural descriptors
Logp, LogD, MW, pKa
70
QSAR structural descriptors
Logp, LogD, MW, pKa pi values, sigma values, size
71
Lead identification approaches
natural products, anti-metabolites, structure based drug design, high throughput screen, in silico drug screening
72
Lead optimization approaches
Structure based drug design, QSAR, isoteric replacement, prodrug
73
Antimetabolites
analogs of endogenous metabolites resemble and essential metabolite and competes with the metabolite in physiological reactions
74
Structure based drug design
design drug based on 3D structure, zanamivir
75
Bio isotere use
Improve pharmacokinetics, selectivity, reduce side effects, simplify synthesis process, avoid patient issues
76
Prodrugs
Inactive or carrier form of a drug that is transformed in vivo, prolong/shorter duration of action, get drug to site, formulation process, decrease toxicity

PHRM 824 Final (4 decks)

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