Prozac is a pharmaceutical used in the treatment of a myriad of mental health problems, ranging from bulimia to obsessive compulsive disorder. It is also known by several other names, including its IUPAC name, N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine, and its generic name, fluoxetine, or fluoxetine hydrochloride. It has the formula C17H18F3NO.
Fluoxetine sets itself apart from the rest with an amine group located near the terminal methyl, at the top of the structure shown above. An amine separates the two benzene rings, and one benzene ring has a carbon attached to three fluorine atoms on its end. Finally, there is one chiral center directly above the benzene ring with only one substituent. It is attached to a hydrogen, the ether, the previously mentioned benzene ring, and to a carbon chain that includes the amine group.
Fluoxetine, CAS number 54910-89-3 , has a melting point of 179-182EC, is a solid at room temperature, and exists as a clear, colorless solution in water, with a odor somewhat similar to mint.. The addition of HCl is used to make is more water soluble, and this is sometimes referred to as fluoxetine hydrochloride. Fluoxetine has a water solubility of 50 mg/mL at 25EC. Its molar mass is 309.326 g/mol, and its IR spectra shows a peak at 1600 and 1475 from the aromatic rings, and a peak at 3300 from the N-H bond. There is also peaks in the 1300-1000 range from the C-O bonds, and a broad 3000 peak from the C-H bonds. NMR spectra is predicted to show multiplets in the 7-8 region from the aromatic rings, a multiplet in the 1-5 region from the N-H bond, a doublet in the 1-2 region from the -CH3, a multiplet from the -CH2 attached to the -NH, and a multiplet from the -CH2 attached to the chiral center. Finally, the H+ attached to the carbon chiral center will be represented by a triplet peak set.
Now that we’ve covered the lovely technical details, let’s take a look at the uses of this controversial pharmaceutical. Fluoxetine is distributed most commonly under the name Prozac by the pharmaceutical giant, Eli Lily. Other companies also produce this compound, and sell it under its generic name, sometimes with their companies name listed after. According to the Prozac website, it is the most widely prescribed antidepressant in the world, and has been used to help over 54 million patients. It is used to treat those suffering from depression, obsessive compulsive disorder (OCD), bulimia, and panic disorder. (“Prozac”) ADHD and several other mental disorders are also treatable with this compound.
Fluoxetine belongs to the family of medications known as Selective Serotonin Reuptake Inhibitors, or SSRI for short. Without delving too far into the subject, SSRIs basically work by keeping serotonin, a neuro transmitter, in the brain. More serotonin in the brain generally is linked to a calming effect on human beings, and may even lead to feelings to euphoria (“Fluoxetine Hydrochloride”). According to one source, fluoxetine is eventually eliminated from the body by the, “R enantiomer degrading more rapidly than the S enantiomer. The liver metabolizes fluoxetine into norfluoxetine (fluoxetine lacking the N-methyl group), which is also a serotonin reuptake inhibitor” (“Fluoxetine Hydrochloride”).
It’s interesting to note that somehow pharmaceuticals, including Prozac, have appeared in water supplies. This is especially intriguing, given the press for greener chemistry in the pharmaceutical industry. In England, and in Canada, Prozac, and other medicines have been found in the drinking water. According to one report, in Canada:
A study by researchers from the National Water Research Institute for Health and Environment Canada, designed to gauge how efficiently plants removed traces of drugs from drinking water, found nine different drugs in water samples taken near 20 drinking water treatment plants across southern Ontario (“Prozac and painkillers found in tap water”).
While the amounts that have been found are very minute, it is still a issue that may continue to grow as modern nations utilize medicines in increasing amounts.
Fluoxetine, as previously noted, is used to treat a variety of mental illnesses. Physicians should just prescribe it for those suffering from these problems, right? Not so fast. Fluoxetine is very controversial medication, and this should be kept in mind before prescribing it to anyone.
While Eli and Lily has been accused of patent infringement over their use of Prozac, the real controversy arises from the possible increased risk of suicide arising from the use of SSRIs. Prozac is not an exception to this tragic phenomenon amongst some SSRIs. As mentioned an article in Fortune about Prozac, it is highly ironic that a drug designed to ward off the negative affects of mental illnesses would lead to suicides, yet this may have been the case for some, as argued by Kim Witczak, who’s husband committed suicide after switching to a SSRI that is a member of the Prozac group of drugs.
Her husband had no history of mental illness, and she (at the time of the article, 2005) was involved in a lawsuit against one of the pharmaceutical giants, and had testified at congressional and FDA meetings. SSRIs have been involved in many lawsuits and legal cases that have taken place over the years, yet many of these have been settled quietly outside of court. In 2004, a warning label was placed on SSRIs, “when they and older antidepressants were shown to double the risk of suicidal thoughts and behavior in children and adolescents” (“Trouble in Prozac”).
Eli & Lily’s website for Prozac states:
Antidepressants increased the risk of suicidal thinking and behavior in children and adolescents with depression and other psychiatric disorders. Patients starting therapy should be observed closely for worsening depression symptoms, suicidal thoughts or behavior, or unusual changes in behavior. PROZAC is approved for use in patients under the age of 18. with depression or obsessive compulsive disorder (OCD) (“Prozac”)
Evidently, SSRIs can be dangerous to some people. However, they have also helped many ward off depression, anxiety, and other problems. Physicians really need to keep both sides of the issue in mind when prescribing these types of antidepressants to their patients. Perhaps if physicians were more well informed about the risks of SSRIs, like Prozac, then some of these tragedies would not have occurred. Further research needs to be done in this area, and more precautions need to be taken by not only physicians, but also by the FDA and pharmaceutical companies. While it’s understandable that companies would want to protect their products, especially ones as lucrative as Prozac, they need to also be clear with the general public about the risks involved with the use of their products. In the long run, a company will be far more trusted and respected by its market for being honest than secretive.
Today we’ve looked at not only the physical and chemical properties of Fluoxetine, but also the uses and importance of it in today’s medical world. The environmental effects of many people using fluoxetine, and other medications has been covered as well. Fluoxetine is a powerful antidepressant, yet dangers do exist in its use. Both physicians and patients need to be aware of the risks and benefits of fluoxetine when considering using it.
References and Works Cited
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Ni, Y G, and R. Miledi. “Blockage of 5HT2C serotonin receptors by fluoxetine (Prozac).” Proc. Natl. Acad. Sci. USA 94 (Mar. 1997): 2036-2040,. PNAS. 15 Apr. 2007 .
“Fluoxetine.” Mental Health. 15 Apr. 2007 .
Staples, Sarah. “Prozac and painkillers found in tap water.” Portland IMC. 15 Apr. 2007
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“Prozac ‘found in drinking water.'” BBC. 15 Apr. 2007 .
Stipp, David. “Trouble in Prozac.” CNNMoney. 15 Apr. 2007 .
“Fluoxetine (APRD00530).” DrugBank. 15 Apr. 2007 .
