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Chiral Drugs
What is chirality?
3.
2.
1'
CH3
2' H
N
pseudoephedrine
d
c
ephedrine
Chiral
centre
d
OH
CH3
2H
N
OH
Chiral
centre
H
1
therapeutic effect.
What drugs in our daily life are chiral?
Questions
1.
H
O
NH
O
S-Thalidomide
HN
O
O
H
Cardiovascular disease:
Atorvastatin calcium, Simvastatin,
Pravastatin sodium and Valsartan
Central nervous system:
Paroxetine hydrochloride and
Sertraline hydrochloride
Respiratory:
Fluticasone propionate and
Salmeterol
Hematology:
Clopidogrel bisulfate
Gastrointestinal:
Esomeprazole magnesium
Antibiotic:
Amoxicillin and potassium
clavulanate
R-Thalidomide
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4. What are the advantages of providing drugs in enantiomerically pure form? How
can single-enantiomeric drugs be obtained in practice?
5. Imagine that you can walk through a mirror into a mirror world where all objects,
including atoms and molecules, exist as their mirror images. Assuming that you
remain unchanged by this transition, i.e. enzymes in your body are not affected and
are still capable of processing molecules in the same way as that in the parent world,
what problem would you encounter during your stay in the mirror world? Explain
briefly.
Hint: In the mirror world, you would not obtain energy by taking sugar labeled as
D-glucose because it is in fact L-glucose, the enzyme-inactive form of glucose.
References
1.
Roger Crossley. (1995). Chirality and the Biological Activity of Drugs. Boca Raton: CRC
Press Inc.
2.
Aboul-Enein & Wainer. (1997). The Impact of Stereochemistry on Drug Development and
Use. Wiley International Publication.
3.
Hava Caner, Efrat Groner & Liron Levy (2004). Trends in the Development of Chiral
Drugs. Drug Discovery Today, Vol. 3 No. 3.
4.
Gordon T. Yee (2002). Through the Looking Glass and What Alice Ate There. Journal
of Chemical Education, No. 5, Vol. 79, 569 571.
5.
6.
http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a600045.html
7.
(2002)
8.
http://www.atchem.net/Catalogalphabetic/cf_cz.HTM
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