Stereochemistry and Organic Chemistry

Drug Action & Metabolism

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The importance of stereochemistry in drug analysis is gaining greater attention in medical biology practice, and a basic knowledge of the subject will be necessary for clinicians to make informed decisions regarding the use of single-enantiomer drugs.   Chirality the most important point is that chiral drugs have 2 structurally similar forms that can behave very differently in biological systems due to their different shapes in 3-dimensional space. These 2 possible forms are termed as enantiomers and the 2 enantiomers of a given chiral drug should be considered 2 different drugs. In biological synthesis chiral drugs synthesises enantiomers of a chiral drug have identical physical and chemical properties in an achiral environment. In a chiral environment, one enantiomer may display different chemical and pharmacology of cancer drug behaviour than the other enantiomer. Because living systems are themselves chiral, each of the enantiomers of a chiral drug can behave very differently in vivo. In other words, the R-enantiomer of a drug will not necessarily behave the same way as the S-enantiomer of the same drug when taken by a patient. The importance of chirality in camptothecin drugs and in all drugs approximately 50% of marketed drugs are chiral, and of these approximately 50% are mixtures of enantiomers rather than single enantiomers.  Racemization refers to the conversion of an enantiomerically pure mixture into a mixture where more than one of the enantiomers are present. If the racemization results in a mixture where the enantiomers are present in equal quantities, the resulting sample is described as racemic or a racemate. Mutarotation is the change in the optical rotation because of the change in the equilibrium between two anomers, when the corresponding stereocenters interconvert. Cyclic sugars show mutarotation as α and β anomeric forms interconvert. The optical rotation of the solution depends on the optical rotation of each anomer and their ratio in the solution.