Advices For Studying Organic Chemistry

5.10 CHIRAL DRUGS

1. Chiral drugs over racemates:
   
   
   1. Of much recent interest to the pharmaceutical industry and the U.S. Food and
      Drug Administration (FDA) is the production and sale of “chiral drugs”.
   
   
   2. In some instances, a drug has been marketed as a racemate for years even though
      only one enantiomer is the active agent.
   
   
   
   


2. Ibuprofen (Advil, Motrin, Nuprin): an anti-inflammatory agent

O

CH 3

OH

H^3 CO

O

H

OH

CH 3

Ibuprofen (S)-Naproxen

1) Only the (S) enantiomer is active.

2) The (R) enantiomer has no anti-inflammatory action.

3) The (R) enantiomer is slowly converted to the (S) enantiomer in the body..

4) A medicine based on the (S) isomer is along takes effect more quickly than the

racemate.

3. Methyldopa (Aldomet): an antihypertensive drug

H 2 N

CO 2 H

HO

HO

CH 3

(S)-Methyldopa

1) Only the (S) enantiomer is active.

4. Penicillamine:

HS

H 2 N

CO 2 H

H

(S)-Penicillamine