Download Group B

Group B
Nicole Yannacone
Anna Leisgang
Matt Edwards
Brett Venable
“Drug May Be First Effective Treatment for Smallpox”
http://www.usatoday.com/news/attack/2001/10/19/smallpox-drug.htm
Editorial:
Stereochemistry is essential in the research and manufacturing of new drugs.
Cidofovir1, sold under the name Vistide2, is synthesized in a way that reduces the racemic
mixture of stereoisomers because only the S-enantiomer is biologically active as an
antiviral drug. The enantiomerically pure form of the drug is recognized by a virus like
smallpox, which enables its destruction, whereas the opposing enantiomer is ineffective.
This concept is known as chiral recognition and is an important concept in modern
pharmaceutical development3.
Initially, the drug was used in the treatment of Cytomegalovirus (CMV)
infections4. Cidofovir was recently approved for the treatment of another virus,
monkeypox, similar to the possible biological weapon smallpox. Since there is no
current antiviral treatment for smallpox, this makes the drug especially important in
consideration of America’s war against terrorism5.
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http://www.chemfinder.com (keyword search: cidofovir)
http://www.gilead.com/webpage_templates/quat.php3?page_name=vistide
http://www.gilead.com
http://www.hivdent.org/drugs/CIDOFOVIR.htm
http://www.usatoday.com/news/attack/2001/11/08/smallpox-usat.htm
Questions:
1. What are the functional groups found in cidofovir?
-Alcohol, Carbonyl, Amine, Ether
2. What medical condition is cidofovir currently treating?
-Cytomegalovirus infections in AIDS patients, monkey pox, possibly smallpox.
3. The IUPAC name for cidofovir is [(S)-1-(3-hydroxy-2phosphonylmethoxypropyl)cytosine]. Would the R enantiomer of the drug be as
effective?
-No, the R-enantiomer of Cidofovir would not be as effective as the S-enantiomer
because it would not have chiral recognition by the virus’ listed above.
4. Identify the chiral center in [(S)-1-(3-hydroxy-2phosphonylmethoxypropyl)cytosine].
-The Carbon connected to the phosphonymethoxypropyl group.
Our group worked very well together. We met several times to work on the
project and each member contributed equally.