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19 Cards in this Set
- Front
- Back
Racemic switches
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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 |
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Ketoprofen
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S: analgesic
R: toothpaste additive |
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Albuterol
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D isomer
promote airway constriction |
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Allegra
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came from seldane
its metabolite |
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Desloratadine
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pure isomer of claritin
taking twice as much drug |
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R fluoxetine
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pure isomer of prozac: depression
S: treat migraine effective for eating disorders |
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Nexium
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S enantiomer of prilosec
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enantiomer
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differ by 1
mirror-like images hands cant overlap rotate plane polarized light differently |
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diastereomer
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1 or more different
NOT mirror images physical properties are different |
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epimer
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differ by 1 chiral center
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geometric isomers
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changes about the double bond
trans v. cis |
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3 pts of binding
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the enantiomers will have differential binding affinities
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1-2 pts of binding
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enantiomers will nto have different binding affinities
similar |
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acetylcholine
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not chiral
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acetylcholine agonists
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3 pt binding
if you take away charge on N.... neutral and lose hydrophobic interaction |
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separation of enantiomers
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enantiomer-- make salt (diastereomer) -- separate via physical method-- remove salt for pure enantiomer
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Production of chiral drugs: Enzymatic Resolution
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ie. chemical reaction catalyzed by lipase
lipase only hydrolyzes 1 of 2 enantiomers one will be ester, one will be acid easy to purify |
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Transaminase
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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 |
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Microorganisms
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conversion of aromatics to chiral diols by bacteria
by enzymes |