Structure Based Therapeutic Evaluations

Question 1

Crum-Brown and Fraser incorrectly hypothesized that muscle relaxant activity requires a __________ _________ group within the structure

Answer 1

Quaternary ammonium

Question 2

True or false: Molecular structure does not influence biologic activity of a drug

Answer 2

False

Question 3

True or false: Each chemical group provides one biological action

Answer 3

False

Question 4

Ehrlich developed the concept of functional groups of drugs exerting their effect by binding with _____ ________

Answer 4

drug receptors

Question 5

Ing hypothesized that ______ and _______ act at the same receptor

Answer 5

Acetylcholine and tubocurarine

Question 6

What explains the blocking effect of tubocurarine?

Answer 6

It is a large molecule that partly occupies the receptor, preventing acetylcholine from interacting with the receptor

Question 7

True or false: Different functional groups can yield similar physical physicochemical properties

Answer 7

True

Question 8

PABA reverses the _______ action of sulfanilamide

Answer 8

Antibacterial

Question 9

Three physicochemical properties that affect relative fit

Answer 9

3d spatial orientation
Functional group shape and size
Acid-base chemistry and related ionization

Question 10

What is a prodrug?

Answer 10

Compounds that are metabolized into their active form once inside the body

Question 11

What are reasons prodrugs are used?

Answer 11

Poor oral bioavailability due to poor GI absorption
Too hydrophobic to be dissolved in aqueous and given intravenously
Chemical instability
Unacceptable odor/taste
GI irritation
Etc.

Question 12

True or false: Most common prodrugs are ethers

Answer 12

False: Esters

Question 13

Esters are readily hydrolyzed by what?

Answer 13

Ubiquitous esterases

Question 14

True or false: Enalapril must be converted to its active form enalaprilat to inhibit ACE

Answer 14

True

Question 15

What is the active functional group of Enalaprilate?

Answer 15

Carboxylic acid. It is hydrolyzed from its ester form

Question 16

What are stereoisomers?

Answer 16

Same # and kinds of bonds, same atoms, same arrangement, DIFFERENT 3D STRUCTURES

Question 17

Enantiomers are pairs of molecules for which the 3D arrangement of atoms are ______________ mirror images

Answer 17

Nonsuperimposable

Question 18

True or false: Diastereomers exhibit the same melting point, boiling point, solubility, and chromatographic behavior.

Answer 18

False

Question 19

The physicochemical properties of a drug depend on what two factors?

Answer 19

Functional groups on the molecule

Spatial arrangement of the atoms

Question 20

Approximately one in how many drugs currently on the market is some type of isomeric mixture?

Answer 20

1 out of 4

Question 21

Differences in what between racemates lead to adverse effects and toxicity?

Answer 21

PK and PD

Question 22

A racemate is indicated by what symbol?

Answer 22

±

Question 23

What is the Cahn, Ingold and Prelog system?

Answer 23

The R & S name system that ranks atoms attached to the chiral center in order of atomic number

Question 24

True or false: Enantiomers can exhibit different biologic actions

Answer 24

True

Question 25

Easson-Stedman Hypothesis

Answer 25

More potent enantiomer must be involved in a minimum of three intermolecular interactions with the surface of the biologic target and the less potent enantiomer with only two sites

Question 26

Diastereomers are molecules that are nonsuperimposable, _______ images

Answer 26

Nonmirror

Question 27

What conditions can result in diastereomer formation?

Answer 27

More than 1 chiral center
Double bonds
Ring systems

Question 28

How do conformational isomers form?

Answer 28

Rotation occurs around 1 bond

Question 29

Explain the difference between anti/staggered conformation and Gauche/skew conformation

Answer 29

Anti- bond angles between groups are 180

Gauche- more stacked conformation of atoms