Prozac molecule

More dramatic examples of how a change in chirality can affect the biological properties of a molecule are found in many drugs, such as fluoxetine, a heavily prescribed medication sold under the trade name Prozac. Racemic fluoxetine is an extraordinarily effective antidepressant but has no activity against... 

Structure is also essential in complex biological molecules. A lot of medicines used for psychiatric illnesses such as depression rely on their ability to interact with certain proteins in the brain. For instance, a class of antidepressants—medications that alleviate the symptoms of depression—act on proteins involved with the collection (reuptake) of the chemical serotonin, and they are known as selective serotonin reuptake inhibitors (SSRIs). This class of antidepressants includes Prozac and Zoloft. Earlier medications were also effective and are still sometimes used though they produce a number of side effects, such as dietary problems. Although an SSRI can also generate potentially dangerous side effects, psychiatrists tend to observe these effects less often. (Brain chemistry is the subject of chapter 3.)... 

FIGURE 2—22. If an inhibitor of the transport carrier binds to its own binding site, it prevents neurotransmitter molecules from being able to bind to their sites. This figure shows an antidepressant, fluoxetine (Prozac), binding to the serotonin transporter. When this drug binds to the serotonin transporter, it essentially bumps serotonin neurotransmitter molecules out of their seats on the transport carrier. This causes inhibition or blockade of neurotransmitter transport into the neuron. Sodium binding is also decreased, and the tires go flat, so that transport is halted. 

FIGURE 2-24. Shown here is how the antidepressant fluoxetine (Prozac) disrupts neurotransmitter from shuttling into the neuron. In this case, binding of the transport carrier by fluoxetine prevents serotonin neurotransmitter molecules from taking a seat on the shuttle. Thus, there is no ride for the serotonin into the neuron. This means that the neurotransmitter serotonin remains in the synapse until it diffuses away or is destroyed by enzymes. 

Chinch Gryniewicz. Ecoscene/Corbis. Reproduced by permission p. 89 Matrix of diamond, photograph. U. S. National Aeronautics and Space Administration (NASA) p. 104 Chaney, Atichael wearing special 3-D glasses to view a computer model of Fluoxetine, or Prozac. Lilly Research Labs, Indianapolis, February 22, 1994, photograph. Corbis. Reproduced by permission p. 115 Three-dimensional computer model of a protein molecule of matrix porin found in the... 

There are several SSRI inhibitors. Their chemical structures are different but they have similar modes of action, namely binding to the SERT. However, they have different pharmacokinetic parameters such as half-life, and differences in adverse effects and drug interactions [54]. Fluoxetine was the first drug of the class, approved in the U.S. in 1987. It is a chiral molecule and the racemic mixture is used as the hydrochloride salt (Prozac , Lilly). It has been approved and marketed in more than 90 countries and used by more than... 

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