Medchem

Question 1

Strong bases have

Answer 1

high solubility

Question 2

Weak bases have

Answer 2

low solubility

Question 3

H-Bond donors

Answer 3

Hydrogens that are attached to N or o

Question 4

H-Bond acceptors

Answer 4

O and N

Question 5

In an amide

Answer 5

N cannot accept H-bonds

Question 6

An increase in one pH unit, means

Answer 6

an 10-fold increase in [H+]

Question 7

Log P >0

Answer 7

more drug in octanol

Question 8

Log P<0

Answer 8

more drug in water

Question 9

ClogP

Answer 9

estimates the logP of molecules

- calculated value

Question 10

Groups w negative values have

Answer 10

increased water solubility and decreased membrane permeability

Question 11

Groups w positive values (logP or ClogP)

Answer 11

decreased water solubility and increased membrane permeability

Question 12

Pro-drugs

Answer 12

A pro‐drug is an INACTIVE drug that is transformed by the body into an ACTIVE drug. Usually this is used to solve a solubility or permeability issue with the
active drug

Question 13

Isomers

Answer 13

Two compounds are isomers if they have the same molecular formula but different chemical structures

Question 14

STRUCTURAL ISOMERS

Answer 14

Same molecular formula, but different bond

connectivity

Question 15

GEOMETRIC ISOMERS

Answer 15

Same bond connectivity, but different arrangement about a fixed bond

Question 16

STEREO‐ISOMERS

Answer 16

Different chirality

Question 17

CONFORMATIONAL ISOMERS

Answer 17

Same bond connectivity, arrangement, and
chirality – but different temporal conformations.
(generally these rapidly interconvert)

Question 18

R-steriochemistry

Answer 18

clockwise

starting Carbon molcule from the dashed wedge then go to colored in wedge

Question 19

S-steriochemistry

Answer 19

counterclockwise

starting from the dashed wedge then go to colored in wedge

Question 20

Enantiomers

Answer 20

have identical physical properties

- if ALL of the stereocenters are switched

Question 21

Diastereomers

Answer 21

have similar (but different) physical properties
-if SOME (but not all) of the stereocenters are
switched

Question 22

Note that a chiral center with a strait line

or squiggly line indicates

Answer 22

a mixture of stereo‐isomers

Question 23

(+) compounds are

Answer 23

chiral molecules that rotate light clockwise

Question 24

(‐) compounds are

Answer 24

chiral molecules that rotate light counterclockwise

Question 25

(+/‐) compounds are

Answer 25

chiral molecules that are racemic

Question 26

Epimerization

Answer 26

The process of converting one stereochemical center into another.

Question 27

Small molecule drugs have

Answer 27

``` < 1000 Da Synthesis Pill (oral) t1/2-Hours High membrane permeability Bio target is intracellular ```

Question 28

Large molecule drugs have

Answer 28

``` > 20000 Da Cellular expresiion taken through IV t1/2- days/weeks Low membrane perm Bio target- extracellular ```

Question 29

Pharmacophore

Answer 29

The key structural components that drive binding to the biological target -A “map” of the “core” interactions that hold a drug in the binding site

Question 30

Amines and carboxylic acids can be inserted for | two purposes

Answer 30

1) To form an ionic interaction with the biological target | 2) To increase the solubility of the drug

Question 31

How do enzymes work?

Answer 31

1) By increasing the “effective concentration” of reactants | 2) By stabilizing the “transition state” of the intermediate

Question 32

Enzymes decrease

Answer 32

activation energy

Question 33

Antimetabolites

Answer 33

designed to “look” like an essential biological molecule – but cannot be processed by a normal metabolic pathway

Question 34

Irreversible inhibitors (suicide inhibitors)

Answer 34

bind covalently to the active site of the enzyme 1. Inhibitor binds 2. Formation of covalent adduct 3. inactivated enzyme - enzyme is usually permanently inactivated

Question 35

Competitive inhibitors sterically

Answer 35

block the active site of the enzyme | -closing the lid of the hopper

Question 36

Potent inhibitor

Answer 36

a molecule that mimics intermediate

Question 37

Noncompetitive inhibitors

Answer 37

``` Binding to allosteric site can activate or inhibit enzyme activity (but usually inhibits... ```

Question 38

Proteases

Answer 38

cleaves an amide

Question 39

Esterases

Answer 39

cleaves an ester

Question 40

Kinases

Answer 40

adds a phosphate (from ATP) to Ser, Thr, or Tyr

Question 41

Phosphatase

Answer 41

removes a phosphate from Ser, Thr, or Tyr