Alyssa De VeraChemistry (H)Period 0

Fluoxetine

Fluoxetine is an antidepressant of the selective serotonin reuptake inhibitor class (SSRI); its common name is more known as the trade terms Prozac or Sarafem. Its main usage is for the treatment of major depressive disorder, obsessive-compulsive disorder, bulimia nervosa, panic disorder, and premenstrual dysphoric disorder.

It first started out as an attempt to find a derivative inhibiting only serotonin reuptake, which is a way to exert psychological and physiological effects in the human brain. David Wong, an Eli Lilly scientist, suggested to retest a series for the in vitro reuptake of serotonin as well as a few others, such as dopamine. Jong-Sir Horng tested this experiment in May 1972 and the results showed the compound that is now known as fluoxetine, was the most potent and selective inhibitor of what they were trying to produce and calculate. Wong published the first article about this compound in 1974 and in 1975 the official chemical name was coined fluoxetine and then it was called its trade name, Prozac by the Eli Lilly and Company, of who sent this compound to the FDA to get approval to later distribute it to potential buyers in pharmaceuticals. The FDA later approved it in in December of 1987, and only a month later before Eli Lilly began marketing the compound. Prozac was later renamed Sarafem once the patent on Prozac expired.

The main medical uses for this compound is to treat major depressive disorder, obsessive-compulsive disorder, post-traumatic stress disorder, bulimia nervosa, panic disorder, premenstrual dysphoric disorder, and trichotillomania. It has also been known to treat some symptoms of cataplexy, obesity, alcohol dependence, and binge eating disorder since the compound holds the elements that trigger and suppresses the emotional responses which link to the disorders listed above. With obsessive-compulsive disorder, it’s stated that high dosage was “much approved” or “very much approved.” With panic disorder, 62% of the patients stated that they had no panic disorders while taking this medication. Fluoxetine is said to be a category C drug for pregnant women as multiple studies indicated that, “he apparent increased risk of fetal cardiac malformations associated with maternal use of fluoxetine has recently been shown also in depressed women who deferred SSRI therapy in pregnancy, and therefore most probably reflects an ascertainment bias. Overall, women who are treated with fluoxetine during the first trimester of pregnancy do not appear to have an increased risk of major fetal malformations.” Those already taking pimozide or Thioridazine should be advised against taking this drug to to its reaction with other chemicals in the body (fluoxetine).

Fluoxetine’s molecular formula is C17H18F3No; also, its systematic name is N-methyl-γ-[4-(trifluoromethyl)phenoxy]benzenepropanamine. The molecular weight is 309.32613 g/mol and an exact mass of 309.134049 g/mol. This compound (in pharmaceutical terms) is taken orally. Some of its physical properties is that fluoxetine’s melting point ranges from 179 to 182 °C and it’s boiling point, which is also high, is 395°C. Fluoxetine’s solubility in water is 50 mg/mL at 25 °C or 14 mg/mL at 20 °C. Other computed properties include: hydrogen bond donor is one; hydrogen bond acceptor is five; and it’s heavy atom count is twenty-two. Fluoxetine’s bioavailability is high at 72% and peak plasma concentrations are achieved from six to eight hours. Its half-life is one to three days (if acute) and four to six days (if chronic). Fluoxetine’s chief active metabolite is norfluoxetine and with that and fluoxetine’s fairly slow

elimination of itself, it’s different from the other antidepressants. With a certain amount of time, fluoxetine and it’s metabolite inhibit their own metabolism and that’s why fluoxetine’s half-life changes from one to three days to four to six days. This means that the concentration of the drug in the blood continues to develop through the first few weeks of initial treatment and a steady concentration is attained at the four-week mark.

Fluoxetine, compared with other antidepressant drugs, is nearly effective with considerably fewer side effects (which relates to its affinity specifically for the serotonin receptor, whereas other drugs interfered with other neurotransmitter systems in the brain).

Some adverse effects are abnormal dreams, abnormal ejaculation, anorexia, anxiety, asthenia, diarrhea, dry mouth, dyspepsia, flu syndrome, impotence, insomnia, decreased libido, nausea, nervousness, pharyngitis, rash, sinusitis, somnolence, sweating, tremor, vasodilatation, and yawning compared to those who took the sugar pill in these trials. Sexual dysfunction can occur, with the loss of libido, anorgasmia, lack of vaginal lubrication, and erectile dysfunction; this is one of the most commonly encountered adverse effects of this treatment. Also, another adverse effect is that it may increase the risk of suicide in people twenty-five and younger. This is based on the increase of suicidal thoughts from that certain age group.

Fluoxetine is a commonly used drug as an antidepressant and if overdosed, the frequent adverse effects include: anxiety, nervousness, insomnia, drowsiness, fatigue or asthenia, tremor, dizziness or lightheadedness as well as many others.