Stereochemistry

Importance of Chirality in Pharmacy

Enantiomers

(S)-(+)-Lactic acid

R/S notation
E/Z notation

(R)-(-)-Lactic acid

Diastereomers
D-Threose

D-Erythreose

Racemate vs Enantiopure
Racemate/ Racemic mixture
Enantiopure/ Enantiomerically pure

Racemate
In a survey of 1850 drugs:
1327 were synthetically obtained
528 contained one or more chiral centers
88.4% were used as a racemate

Enantiomers in Biological
Systems

Thalidomide

Contergan

Thalidomide became anover the

counterdrug in Germany on October 1, 1957.

Shortly after the drug was sold, in Germany,

between 5,000 and 7,000 infants were born
withphocomelia(malformation of the limbs).

Throughout the world, about 10,000 cases were

reported of infants withphocomeliadue to
thalidomide; only 50% of the 10,000 survived.

Contergan

Today, thalidomide is being marketed

byCelgenemainly as a treatment of certain
cancers and of a complication ofleprosy.

Enantiopure
To separate unwanted
effects if they reside
exclusively in one
enantiomer
Less drug dosage
Easier assessment of
drugs

Escitalopram

Disadvantages
Complexity of process
Cost
Thermodynamically unstable causing
racemization to occur

e.g. Thalidomide undergoes racemization in

aqueous media

Conclusion

Enantiomerically pure drugs are genarally

preferred over racemates

Disadvantage lies at the cost and the

technology needed to separate the
enantiomers