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Chemistry

College Presentation
by

Nour H

on 4 April 2015

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Transcript of Chemistry

Ibuprofen
Resolution of Racemic Mixture
Reaction with an optically active base or acid gives a pair of diastereomeric salts.

Members of this pair exhibit different physicochemical properties (solubility, Melting point, …) and can be separated owing to these differences.

A solution in which both enantiomers of a compound are present in equal amounts is called a
racemic mixture.

Absolute configuration is the arrangement of atoms in a chiral molecule.
Thalidomide
Raemic drug which was used as a sedative to treat insomnia and reduce nausea associated with pregnancy.

In 1960, Harmful side effects of thalidomide were reported. Patients’ nerves in their hands and feet deteriorated.

Worse still, thalidomide was later found to cause severe birth defects when taken by pregnant women.

Stereoisomers
Isomeric molecules that have the same molecular formula, but that differ in the three-dimensional orientations.
Ibuprofen is a chiral drug which is used as anti-inflammatory.

The pharmacological properties of ibuprofen is induced by S-enantiomer only.

However, a portion of R-ibuprofen is metabolically inverted to S-ibuprofen, thus increasing the bioavailability of drug.

Role of
Stereochemistry
in Pharmaceutical Science

Babies were born with hands and feet protruding directly from their torsos, a condition known as phocomelia. Others had limbless trunks with toes extending from their hips.

Enantiomers
molecules that are non superimposable mirror images of one another resulting from the chirality.
Thalidomide (cont.)
R-thalidomide is a sedative, but S-thalidomide is a teratogen, which inhibits new blood vessel growth.
Unfortunately, the human liver contains an enzyme that can convert R-thalidomide to S-thalidomide.

Therefore, even administration of enantiomerically pure R-thalidomide results in a racemic mixture.

Cetirizine
Cetirizine consists of equal parts R- and S-enantiomer, with an anti histaminic effect.

But several studies have shown that the pharmacological effect is induced by the R-enantiomer (Eutomer) only. While The S-enantiomer has no shown effects (Distomer).

The R-enantiomer is not converted into an S-enantiomer after ingestion.

Reference
http://www.ncbi.nlm.nih.gov/pubmed/2207301
http://www.irf.dk/en/reviews/xyzal_levocetirizine.htm
http://en.wikibooks.org/wiki/Structural_Biochemistry/Organic_Chemistry/Stereochemistry
https://www.google.com.eg/?gfe_rd=cr&ei=MbnKU93_O83Q8gel9YGYBA&safe=on&gws_rd=cr#safe=active&q=sterioisomers
http://chemwiki.ucdavis.edu/Organic_Chemistry/Chirality/Chirality_and_Stereoisomers
http://www.docbrown.info/page07/isomerism2a.htm
http://en.wikipedia.org/wiki/Thalidomide
http://www.chemgapedia.de/vsengine/vlu/vsc/en/ch/12/oc/vlu_organik/stereochemie/trennung_enantiomere.vlu/Page/vsc/en/ch/12/oc/stereochemie/trennung_von_enantiomeren/trennung_von_enantiomeren.vscml.html

A curved arrow is drawn from the highest priority substituent to the lowest priority substituent.

Thank you
Why can't we give patients only the (R)-thalidomide?
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Task Distribution
Norhan Hesham Mohammed 782 Presentation and Prezi Design
Nourhan Amr Farouk 769 Introduction
Nourhan Mahmoud Ali 777 Thalidomide
Nourhan Sadek Kamel 763 Cetrizine
Norhan Adel Abdel-Razik 766 Ibuprufen
Nourhan Abdel Hakim Ibrahim 768 Separation
Nourhan Mohamed Abdullah 774 Separation
Nourhan Essa Ramadan 770 Chem sketch
Full transcript