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PHRM 824 Final > Exam 1 Material > Flashcards

Exam 1 Material Flashcards

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
Q

bigger logP means

A

More hydrophobic

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26
Q

Explain why the relationship of drug effectiveness vs LogP is parabolic

A

Lipophilicity improves drug permeation but too much may hinder crossing

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27
Q

Calculate ClogP

A

Sum of Pi values
lower number means more acidic

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28
Q

Estimate LogD

A

LogD = LogP - (pH-pKa)
When pH is bigger than pKa it is first in equation

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29
Q

When are drugs most absorbed?

A

Where they are mostly neutral

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30
Q

Location with pH of 5-7

A

jejunum and duodenum

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31
Q

Location with pH 6-8

32
Q

Location with pH 1-3

33
Q

Can a quaternary amine be absorbed?

A

No, tubocurarine fine to eat not orally available

34
Q

What makes electronic effects weaker

A

going through multiple bonds

35
Q

Positive sigma value

A

Electron withdrawing, more acidic, lower pKa

36
Q

Negative sigma value

A

electron donating, less acidic, higher pka

37
Q

Meta position

38
Q

Para position

39
Q

Ortho position

40
Q

Resonance effect

A

Ortho and para positions
Through pi bonds

41
Q

Inductive effect

A

Ortho and para positions
Through sigma bonds

42
Q

Only inductive effect

A

Meta position

43
Q

electron donating

A

Negative sigma value, increase pKa, decrease acidity

44
Q

Electron withdrawing

A

Have unshared electron pair, ortho para directing

45
Q

Fluorine characteristic

A

Metabolism resistant

46
Q

Isoteres

A

similar shapes and electronic effects
H and F

47
Q

Stereoisomers

A

Mirror images, 1+ chiral centers, same properties except for optimal rotation

48
Q

R/S

A

Absolute configuration, 3D arrangement, primary method

49
Q

d/l

A

Optimal rotation, experimentally determined, dependent on solution conditions

50
Q

D/L

A

Relative configuration to glyceraldehyde, only for amino acids and sugars

51
Q

S notation

A

Counter clockwise

52
Q

R notation

53
Q

The more potent

A

the more interactions with receptors needed

54
Q

List factors other than receptor binding that result in different biological properties of drug enantiomers

A

Permeation by transporters
Nonspecific binding to serum proteins
Metabolism

55
Q

Issues of racemic drugs

A

Separation is difficult and costly
inactive is physiologically inert

56
Q

Enantiomers

A

non superimposable mirror images

57
Q

Diastereomers

A

not mirror images

58
Q

Geometric isomers

A

have double bonds cis z and trans e

59
Q

KD value at 1

A

100% occupied

60
Q

KD value at 0

A

0% occupied

61
Q

DeltaGD=-RTlnKD

A

R = gas constant 8.314
T = temp in kelvin

62
Q

Change in KD from deltaGD

A

Reduce KD 10 fold, add 1.4 to G

63
Q

Hydrophobic interactions

A

Between nonpolar groups in water

64
Q

Electrostatic interactions

A

+ and - , long distances

65
Q

Hydrogen bonding

A

O and N with H in middle

66
Q

Aromatic ring interactions

A

Faces electron rich
Edges electron deficient
Pi stacking, T stacking

67
Q

Atorvastatin and HMG-CoA reductase

A

Hydrophobic interaction

68
Q

QSAR

A

Mathematical, correlation between structure and activities
Derived by statistical regression
Receptor info not needed

69
Q

QSAR structural descriptors

A

Logp, LogD, MW, pKa

70
Q

QSAR structural descriptors

A

Logp, LogD, MW, pKa
pi values, sigma values, size

71
Q

Lead identification approaches

A

natural products, anti-metabolites, structure based drug design, high throughput screen, in silico drug screening

72
Q

Lead optimization approaches

A

Structure based drug design, QSAR, isoteric replacement, prodrug

73
Q

Antimetabolites

A

analogs of endogenous metabolites
resemble and essential metabolite and competes with the metabolite in physiological reactions

74
Q

Structure based drug design

A

design drug based on 3D structure, zanamivir

75
Q

Bio isotere use

A

Improve pharmacokinetics, selectivity, reduce side effects, simplify synthesis process, avoid patient issues

76
Q

Prodrugs

A

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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