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Published byTyler Dickerson Modified over 6 years ago
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Biological synthesis reactions within cells ( in vivo) produce only one enantiomeric form. However, when drugs are produced by synthetic processes outside the body (in vitro), they yield a mixture of enantiomers known as a racemate. Pharmaceutical companies face the challenge of finding out the physiological effects of each isomer, before determining whether the drug can be marketed as the racemic mixture or whether a single enantiomer must be produced. The motivation for this research activity came from the thalidomide tragedy. Thalidomide was produced and sold as a racemic mixture. However, it was later discovered that only one of the isomers had a beneficial effect. The other isomer was teratogenic, meaning that it caused serious deformities in the fetus.
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Many drugs are marketed as racemates, including fluoxetine (Prozac) and the anti-inflammatory drug Ibuprofen. However, it is becoming more common to develop drugs as single enantiomers. It is estimated that of the chiral drugs on the market, approximately 50% are single enantiomers.
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Taxol – a powerful anti-cancer drug
Taxol, also known as Paclitaxel, belongs to a group of compounds known as taxoids. Taxol has potent effects against solid tumors and it is used primarily in the treatment of breast and ovarian cancers. Taxol binds to a protein called tubulin in cells. Tubulin is the main component of microtubules, which form structures called spindles during cell division. When the Taxol binds at the microtubules , it prevents the spindle fibers from breaking down, and this halts the cell division cycle. In this way taxol prevents the growth of a tumor.
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Chiral auxiliary
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