stereochemistry in pharmacy and drug therapy
DESCRIPTION
Brief highschool presentation on an introduction to stereochemistry and chiraltyTRANSCRIPT
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Stereochemistry Importance of Chirality in Pharmacy
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R/S notation E/Z notation
Enantiomers
(S)-(+)-Lactic acid (R)-(-)-Lactic acid
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DiastereomersD-Threose D-Erythreose
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Racemate/ Racemic mixture Enantiopure/ Enantiomerically pure
Racemate vs Enantiopure
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In a survey of 1850 drugs: 1327 were synthetically obtained 528 contained one or more chiral centers 88.4% were used as a racemate
Racemate
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Enantiomers in Biological Systems
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Thalidomide
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Thalidomide became an over the counter drug in Germany on October 1, 1957.
Shortly after the drug was sold, in Germany, between 5,000 and 7,000 infants were born with phocomelia (malformation of the limbs).
Throughout the world, about 10,000 cases were reported of infants with phocomelia due to thalidomide; only 50% of the 10,000 survived.
Contergan
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Today, thalidomide is being marketed by Celgene mainly as a treatment of certain cancers and of a complication of leprosy.
Contergan
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To separate unwanted effects if they reside exclusively in one enantiomer
Less drug dosage Easier assessment of
drugs
Enantiopure
Escitalopram
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Complexity of process Cost Thermodynamically unstable causing
racemization to occur◦ e.g. Thalidomide undergoes racemization in
aqueous media
Disadvantages
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Enantiomerically pure drugs are genarally preferred over racemates
Disadvantage lies at the cost and the technology needed to separate the enantiomers
Conclusion