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19 Cards in this Set

  • Front
  • Back
Racemic switches
economic considerations
-overcome patent protection
-circumvent generics
-sepracor: company founded to do this

biological considerations
-active isomer
-nonactive isomer: side effects
-different pharmaco/metabolic profiles
Ketoprofen
S: analgesic
R: toothpaste additive
Albuterol
D isomer
promote airway constriction
Allegra
came from seldane
its metabolite
Desloratadine
pure isomer of claritin
taking twice as much drug
R fluoxetine
pure isomer of prozac: depression
S: treat migraine
effective for eating disorders
Nexium
S enantiomer of prilosec
enantiomer
differ by 1
mirror-like images
hands
cant overlap
rotate plane polarized light differently
diastereomer
1 or more different
NOT mirror images
physical properties are different
epimer
differ by 1 chiral center
geometric isomers
changes about the double bond
trans v. cis
3 pts of binding
the enantiomers will have differential binding affinities
1-2 pts of binding
enantiomers will nto have different binding affinities

similar
acetylcholine
not chiral
acetylcholine agonists
3 pt binding
if you take away charge on N.... neutral and lose hydrophobic interaction
separation of enantiomers
enantiomer-- make salt (diastereomer) -- separate via physical method-- remove salt for pure enantiomer
Production of chiral drugs: Enzymatic Resolution
ie. chemical reaction catalyzed by lipase
lipase only hydrolyzes 1 of 2 enantiomers
one will be ester, one will be acid
easy to purify
Transaminase
chemical reaction catalyzed by transaminase to produce an enantiomeric amine... create pure enantiomer

chemical reaction catalyzed by transaminase to degrade an unwanted enantiomeric amine... make achiral ketone
Microorganisms
conversion of aromatics to chiral diols by bacteria
by enzymes