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z F1: Med Chem > Exam 3 > Flashcards

Exam 3 Flashcards

1
Q

The first molecule with the desired pharmacological activity is the …

A

Lead compound

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2
Q

Testing the purification of active compounds from plants, microbes, and animals is known as

A

Natural sources

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3
Q

The scientific study of ethnic groups, physical habits, and how they use medicinal planes

A

Ethnopharmacology

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4
Q

Testing a variety of compounds using a bioassay

A

Screening

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5
Q

Libraries of all compounds on hand

A

Random libraries

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6
Q

Synthetic libraries made up of only drug like molecules

A

Directed libraries

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7
Q

Using a computer modeling program go test compounds in computer for ability to fit in a binding cavity or for 3D similarity to natural ligand

A

In Silico Library

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8
Q

Identify target molecule
Design high potency enzyme inhibitors based in substrate, products, and reaction mechanism

A

Rational drug design

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9
Q

Special type of drug design where 3D structure of the target is used to direct the synthesis of new compounds

A

Structure based design

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10
Q

What is the goal of lead modification

A

Make lead compound fit it’s target better increasing its potency and specificity

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11
Q

SAR: understand the relationship between each drugs _________ and it’s ________

A

Structure and activity

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12
Q

3D arrangement of atoms that is responsible for the drugs activity

A

Pharmacophore

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13
Q

3D arrangement of atoms that is responsible for the metabolic properties

A

Metabophore

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14
Q

3D arrangement of atoms responsible for toxicity-eliciting interactions

A

Toxicophore

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15
Q

Simplification makes the compound easier to synthesize and tells us which groups are _______ which are ______

A

Needed and not needed

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16
Q

Deletion studies identify the ___________ which is the portion of a molecule containing essential functional group that directly interact with the target

A

Pharmacophore

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17
Q

The pharmacophore included the _______________ of those critical functional groups

A

3D arrangement

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18
Q

Inserting a methylene group between two parts of a drug molecule is called

A

Homologation

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19
Q

Adding a branch point can have what kind of effects on the drugs activity

A

It can increase or decrease its activity

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20
Q

In ring chain transformations atoms can rotate freely around carbon-carbon _______ bonds and this free rotation will often produce different ___________

A

Single
Conformations

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21
Q

Introduction of rings restricts the shape of a molecule making it more ________ sometimes increasing the molecules potency or making it more specific

A

Rigid

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22
Q

Breaking rings or removing them will slow a molecule to be more _________ this molecules might be able to alter its shape and fit more receptors but it also might produce more side effects

A

Flexible

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23
Q

Converting single bonds to double bonds will after geometry and may ______ the molecule

A

Rigidify

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24
Q

Bioisosteres are functional groups that possess almost equal _____________ and _____________

A

Molecular shapes and volumes
Similar distribution of electrons

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25
Q

Hydrogens are the same size as what

A

Fluorine

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26
Q

Methyl is the same size as what

A

Chlorine

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27
Q

The more polar and charged the molecule the ______ well absorbed

A

Less

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28
Q

More lipophilic to point of non-dissociation is ______ absorbed

A

Less

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29
Q

Reducing the number of charged groups on a drug decreases it’s water solubility however this conversion is only _________

A

Temporary (will cleave back to normal molecule)

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30
Q

A hERG pharmacophore has a lipophilic base that has a ________ _______

A

Tertiary amine (2-5 atom chain that includes rings, hetero atoms or polar groups)

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31
Q

Excretion ____________ removes drug from the body. The major excretory organ is the ______

A

Physically
Kidney

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32
Q

What drugs are excreted often without needed major metabolism

A

Polar and ionized drugs

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33
Q

Lipophilic drugs are largely _____________ back into systemic circulation during passage through renal tubules

A

Reabsorbed (require modification to make them more polar)

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34
Q

The metabolism of lipophilic drugs into more _________ metabolites is essential for the elimination of these compounds from the body

A

Hydrophilic

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35
Q

Phase 1 metabolism: polar functional groups are

A

Introduced into the molecule or modified by reactions

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36
Q

Phase II modification (conjugation)

A

Attaching small, polar, and ionizable endogenous molecules to phase I metabolite or parent drug

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37
Q

What are the 4 things that can happen in an oxidation reaction

A

Gain of oxygen
Loss of hydrogen
Loss of alkyl group
Loss of hetero atom

38
Q

Isozymes

A

Multiple forms of same enzyme

39
Q

What CYP families cause the most of the drug metabolizing enzymes

A

CYP 1,2,3

40
Q

Unsubstituted phenyl rings are hydroxylated to ______ ________

A

Arene Oxides

41
Q

Arene Oxide spontaneously rearranges to give a ______ hydroxylated product

A

para (NIH shift)

42
Q

EWG groups ___________ rings causing a __________ in -OH

A

deactivate
decrease

43
Q

EDG groups ___________ rings causing a __________ in -OH

A

activate
increase

44
Q

Oxidation of alkenes

A

non aromatic carbon-carbon double bonds can be oxidized
Results in epoxide
Epoxide can be open to produce a diol

45
Q

Oxidation only occurs if there is a ________ atom on each alkene carbon

A

hydrogen

46
Q

Allylic carbons are aliphatic carbons directly adjacent to ________________ double bonds

A

non-aromatic

47
Q

Benzylic Carbons are aliphatic carbons ___________ attached to an aromatic ring

A

directly

48
Q

Oxidation does not usually occur if there is a __________ attached to the benzylic carbon as well

A

heteroatom

49
Q

Aliphatic chains will undergo oxidation at the terminal methyl group or at the ____________ carbon

A

penultimate

50
Q

In general, you need how many unbranched carbons in order to get oxidation

A

3-4

51
Q

Oxidation will occur at either omega or omega-1 but ___ ______ since one is usually enough to increase water solubility and facilitate excretion

A

not both

52
Q

For deamination the alpha carbon must contain at least one _________ atom. This amine attached quaternary carbons cannot undergo deamination reactions

A

Hydrogen

53
Q

N-dealkylation can occur on what three types of molecules

A

2, 3 amines and amides

54
Q

N-oxidation involves direct oxidation of the __________ instead of the adjacent carbon atom

A

Nitrogen atom

55
Q

Dealkylation of ethers usually only occur when it is a _______ ether because of steric hinderance

A

Methyl

56
Q

Oxidative dehalogenation usually occurs when

A

-Requires two halogens on carbons
-Have to remove hydrogen so 3 halogens is too many

57
Q

The reduction of a functional group on a drug will result in the gain of what

A

Hydride ion

58
Q

How are aldehydes formed

A

Oxidative deamination or N, O, or S-dealkylation

59
Q

All reductions reactions require a source of electrons which is usually carried in the electron carrier

A

NADPH

60
Q

Ketones can be reduced to what

A

2’ alcohol

61
Q

Azo group (N=N) can be used in a

A

Prodrug strategy

62
Q

You usually only see nitro groups when it is attached directly to what

A

an aromatic ring

63
Q

The unmasking of polar groups does what to water solubility

A

Increases

64
Q

Functional groups that are most accessible are most _____________ to metabolism

A

Susceptible

65
Q

Conjugation reactions involve attaching small, polar, and ionizable _______ ________ to phase 1 metabolite or parent drug to further increase water solubility

A

Endogenous molecules

66
Q

Phase 2 metabolism requires what two things

A

High energy molecule
Enzyme

67
Q

Most conjugates are biologically inactive and usually nontoxic because they are highly polar and unable to cross cell membranes. What are the two exceptions

A

Acetylation
Methylation

68
Q

In order for glucuronic to be added to drug molecules, it first has to be converted into a high energy intermediate called what

A

UDP-Glucuronate

69
Q

In a glucuronic acid conjugation the stereo center at C1 is __________ during the nucleophilic attack by the drug

A

Inverted

70
Q

Sulfate conjugation occurs primarily with what

A

Phenolic OH

71
Q

In for for sulfate to be conjugated to drugs, it also has to be converted into a high energy intermediate is called what

A

3’-phosphoadensine 5’phosphosulfate (PAPS)

72
Q

Sometimes sulfate conjugation is unstable and this can be susceptible to nucleophilic attack by various proteins causing what

A

A toxic metabolite

73
Q

What does amino acid conjugation usually occur with

A

Aromatic COOH
Aryl acetic COOH
(Requires activation of amino acid before attachment to drug)

74
Q

Glutathione conjugation requirements

A

Can react with large functional groups
Does not require activation before attachment to drug

75
Q

Actuation increases __________. Acetylation is usually used to terminate ________ activity and not necessarily increase excretion

A

Lipophilicy
Physiological

76
Q

Methylation occurs on what

A

Catecholes
Phenolic OH
Amines
Thiols

77
Q

Inactive material requiring conversion, usually by metabolism, to an active drug

A

Prodrug

78
Q

Typical functional groups used in the creation of prodrugs

A

Carboxylic acids and alcohols (convert to ester)
Amines (convert to Azo or Amide)

79
Q

Prodrugs can improve high hydrophilicity

A

Poor oral bioavailability due to inability to cross membrane
Incompatibility with lipid based formulation

80
Q

Prodrugs can improve chemical instability

A

Drug is inactivated before it reaches its site of action

81
Q

Prodrugs can improve poor aqueous solubility

A

Drug can’t be formulated in water solutions for injection
Solid forms of the drug don’t dissolve well producing poor and variable oral bioavailability

82
Q

Prodrugs can improve 1st pass metabolism

A

Orally administered drug is rapidly inactivated by drug metabolizing enzymes in the intestine and liver before reaching general circulation

83
Q

The longer the alkyl chain on the ester the more lipophilic = deep intramuscular injection = ______ ______ ______

A

Longer half life

84
Q

In double esters the eaters will cleave off the _______ which will unmask the second ester, which will spontaneously decompose to ______

A

1st ester
-COOH

85
Q

You can also use the acetoxymethyl method to mask a phosphate groups which does what to the drug

A

Reduce the charge and increase absorption
Get the phosphate back

86
Q

Cleaving by eaters enzymes can make a diet more resistant to cleavage making the drug slower to convert from inactive prodrug to active drug what does this mean for the body

A

Active drug released at slow steady rate = extended release

87
Q

Soft drugs undergo a metabolic ________. This is because they have a soft spot and causes the drug to have a fast metabolism

A

Inactivation

88
Q

What are some benefits of soft drugs

A

Precise control over duration of action
Obtain better steady state
Avoid toxicity due to over medication
Limit drug distribution for topicals

89
Q

__________ is hydrolysis fast which inactivated compounds making the molecule have a short half life

A

Ester

90
Q

When the ester is added to the outside of the drug it is converted to a what

A

Carboxylic acid (this is negatively charged at pH 7)

z F1: Med Chem (3 decks)

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